Did you know that Richard Gere had it going with Cindy Crawford during the Julia Roberts and “Pretty Woman” days? Were you aware that the princess of rock n’ roll married the King of Pop? The celebs dated one another in turns, making sure they all got a taste of each other. Now, you tell us how many times Johnny Depp appears on the list.
Alyssa Milano and Corey Haim
Like many child stars (and adult ones), Corey Haim had substance dependency issues during the 1980s'. He was a teen idol and dated some young ladies during those days, with Alyssa Milano being the most famous of them all.
She was a huge star at the time, with "Who's the Boss?" and would go on to be an even bigger star with roles in hit shows like "Charmed" and "Mistresses". They dated for a few years and broke up at the beginning of the 1990s'. He must have left his mark on Alyssa's life, as she was devastated when she learned about Corey's passing in 2010.
Dennis Quaid and Lea Thompson
The movie "Jaws- 3" brought us a bit more than scary sharks. In 1996, Lea Thompson and Dennis Quaid (who starred in the movie) were seriously dating, and Dennis even proposed. The two were engaged for almost a year but never took the next step.
A few years later, Thompson started to date Howard Deutch, who she met on the set of "Some Kind of Wonderful" and ended up marrying. It seems that Lea Thompson has a thing for men she meets on sets. Then again, these things are bound to happen when people are literally paid to play each other's love interest.
Gwyneth Paltrow and Brad Pitt
In the 1980s and 1990s, you couldn't get better looking than Brad Pitt and Gwyneth Paltrow. They were the most glamorous couple of that era and were adored by all. They dated for two years, which at the time seemed like a lifetime.
A few years later, Gwyneth Paltrow admitted that their relationship ended because she was in a very unstable time in her life and that she practically messed it up. You never know; Paltrow could have saved us the whole Anniston-Jolie story if she would have stuck around. Though it seems like they both landed on their feet eventually.
January Jones and Ashton Kutcher
January Jones and Ashton Kutcher were pretty much leveled out when they first met in 1998. They were both in the spring of their careers, still taking any role proposed, and were working their way up the success ladder. They dated for three years and decided to go on their separate ways in 2001.
Jones has remarked on several occasions that Kutcher was not the ideal partner and was not supportive of her career at all. Since then, the couple kept climbing, though separately. Jones went on to star as Betty Draper in "Mad Men" and Ashton went on to marry Mila Kunis.
Drew Barrymore and Luke Wilson
Many couples start their love story on the sets of a movie, and so did Luke Wilson and Drew Barrymore. "Home Fries" and "Best Man" were where it all began for these two. It must make things so easy when your on-screen partner is your real-life partner.
They started to date in 1997 but only lasted until 1999. Barrymore has said in a number of interviews that Luke Wilson is one of the most important people in her life and that she has been privileged to have known him. We feel he's not the only guy Drew said this about...
Madonna and Sean Penn
Sean Penn and Madonna met in the winter of 1985 and married soon after, in August of the same year. That's a good way to make one year the best in less than six months. "True Blue", one of Madonna's greatest albums, was, in fact, dedicated to Penn.
In January 1989, just before celebrating their fourth anniversary, they decided to call it quits and got divorced. None of them seems to have wallowed in it for too long. They have since moved on, with Sean Penn remarrying twice (one to actress Robin Write and once to actress Leila George) and Madonna remarrying once (to filmmaker Guy Ritchie).
Melanie Griffith and Don Johnson
Don Johnson and Melanie Griffith starred in the last three decades of the 20th century. The mid-1970s is when it all began. Less than a year after they married, they already got divorced, only to retie the knot in 1989.
That second round only lasted for five years during which the two became parents to actress Dakota Johnson who you probably know from the 50 Shades franchise. The mid-1990s were the days when Jonson and Melanie eventually realized that they weren't meant to be, and 1996 was the year they ended the love story for good. What a rollercoaster of a relationship!
George Clooney and Kelly Preston
We bet you never knew that Mr. Nespresso, George Clooney, had a guest appearance on the 1980s show "The Facts of Life." Well, he did, and at the same time (and we didn't know this until researching for this article), he dated Kelly Preston before she went off and married John Travolta.
They dated in 1988, which lasted for only a year, but during that year, they moved in together and even raised a pet pig named Max! After the breakup, Clooney kept the pig and raised it until died at the old age of 18. Who knew he had it in him?
Julia Roberts and Matthew Perry
A pretty woman and one of the funniest guys in the house kicked it off, apparently in 1995. Julia Roberts, known for her remarkable performance in many widescreen movies, was a guest star on "Friends," Mattew Perry's home set. Ironically, Roberts played the role of someone who gets payback on Perry's Chandler for bullying her in school.
The two enjoyed each other's company for almost a year before deciding to end the romance. It is thought that this was the turning point for Mattew Perry, as his drinking problem is said to have begun slightly after the breakup, but this is all hearsay.
Sandra Bullock and Matthew McConaughey
These two did a very good job of hiding their relationship. So much so, that by the time the tabloids realized they were an item, they had already broken up. Apparently, Bullock and McConaughey were together for almost two years and even got engaged secretly!
They met in 1996 and immediately felt the sparks while filming on the same set. For their own reasoning (they kept this a secret, too), they decided to go on their separate ways; however, they have remained close until today. They are very close friends and make it a point to share it with the world.
Arsenio Hall and Paula Abdul
"American Idol" judge Paula Abdul dated Arsenio Hall, who had his very own show. The two met on the set of a movie and lived hectic lives in the entertainment industry. They met while filming "Coming to America," which was a classic Eddie Murphy comedy, and became inseparable.
Even though they broke up, Arsenio mentions that he has only good memories of Paula. They stayed friends, and she even appeared on his show after they broke up. Abdul has since married twice (actor Emilio Estevez and fashion designer Brad Beckerman) but Hall has never married, though he does have one son.
Janice Dickinson and Rob Lowe
Like everyone in the 1980s', all men wanted to be Rob Lowe, and all women wanted to date Rob Lowe. And Janice Dickinson is one woman who actually did that. 1988 was the year it all happened, though it only lasted a few months.
She was a stunning supermodel who escalated her career and later became one of the judges on "America's Next Top Models," in addition to being a successful businesswoman and author. Rob Lowe, on the other hand, is a loved actor, producer, and director, but the 1980s will always be remembered as his peak and pride decade.
Cher and Val Kilmer
Movie stars and musicians of the 1980s and 1990s', practically lived in the same bubble. They mixed with the same people, mingled at the same parties, and dated the same loved ones. Cher, who was at the peak of her career in those days, set her eyes on Val Kilmer, who later co-starred in "Top Gun" with Tom Cruise.
They were a hot item between 1982 and 1984 and then called it quits. Cher said that Kilmer was much younger than her, which was a big issue back in the day, and that older guys (or guys the same age as she was) just weren't interesting enough for her.
Michal Jackson and Brooke Shields
Unlike today, at the beginning of the 1980s, things were different, and the number of stars was limited. Not every artist that came up with a new song instantly became famous, whereas today, you don't need much to be recognized worldwide. Michal Jackson, at the time, was known and loved globally. As was Brooke Shields
He dated Brooke Shields for a while, but apparently, they weren't both aligned with how they wanted things to go. Jackson proposed a number of times; however, Shields tells a different story and has always claimed that they were no more than two good friends.
Christina Applegate and Brad Pitt
In the '80s, Brad Pitt and Christina Applegate were (like many well-known stars at the time) in the spring of their careers. Pitt just started to walk through the path of fame, and Applegate was breaking through with her role in "Married With Children." These two were friends as teenagers.
Pitt (together with other future stars such as Jason Priestly) would come to her parent's house for Sunday lunches. Pitt was even her date to the 1989 MTV Movie Awards, though she left with someone else… awkward! They both went on to other partners eventually, though. Applegate is now married to musician Martyn LeNoble, and Pitt, well... we all know what happened with him.
Christine Taylor and Neil Patrick Harris
Dr. Doogie Howser is not all a goody two shoes. Way before he came out and revealed to the world his orientation, he dated actress Christine Taylor. She is best known and loved for her role in "The Brady Bunch" and in "The Wedding Singer." They dated from 1997 until 1998. A relationship that lasted just over a year.
They were a relatively private and quiet couple, with not too many horror stories to make the paparazzi's day. These days, Doogie is happily married to David Burtka, and Christine is married to Ben Stiller, also in a very happy way.
Robert Downey Jr. and Sarah Jessica Parker
Way back in the 1980s, Robert Downay Jr. was still unknown for his roles as Iron Man in the MCU. In fact, he was so out of it with his substance dependency that it seems that Sara Jessica Parker came just in time to put him back on his feet.
The two were filming a movie together, ending in a seven-year relationship. Downey found it hard to let go of his former lifestyle, which was difficult for Parker to handle. Since then, he has left his mark in "Chaplin" and "Sherlock Holmes," and Parker has left us wondering whatever happened to Mr. Big and the City.
Lisa Marie Presley and Michael Jackson
This is about as good as it gets. The King of Pop dated the King of Rock n Roll's daughter. AKA the Rock n Roll princess. The early 1990s were the days when everything was about Michael Jackson's legal accusations, and Lisa Marie managed to make the wind blow in a different way.
Lisa Marie even famously starred in Jackson's music video for his ballad "You Are Not Alone". They were married for under two years and had no children together, yet they managed to preserve their titles, which they both left as their legacy following each of their deaths.
Winona Ryder and Matt Damon
Sometimes in life, all you need is a best friend to introduce you to their partner's best friend, and there you go. You get yourself a boyfriend. In the late 1990s', Gwyneth Paltrow was Winona Ryder's best friend. Paltrow was also dating Ben Affleck. Matt Damon was Affleck's best friend and you can see where this is going.
The two hit it off and a match was made. Damon and Ryder dated for over three years and were known as Hollywood's hottest couple back then. Matt Damon quickly moved on to his next story in life, and Winona Ryder wasn't left far behind.
Elle Macpherson and Billy Joel
Apparently, you don't have to be the best-looking guy in the class to date the most beautiful girl around. Well, that's how it was back in the 1980s'. Back then, the known and loved "Piano Man" was (and still is) a successful musician and one of the best-selling artists of all time.
During those days, Joel started to date Elle Macpherson, who back then was (and still is) a beautiful model making her way through law school (though that law part was only true for about a year). The two dated for a short time and then decided to go their own way.
Courtney Love and Edward Norton
Courtney Love's most famous relationship was and will always be the one she had with the late Kurt Cobain but this entry is about a different relationship. The movie "The People vs. Larry Flynt" is where it all began. Norton and Love co-starred and started to date shortly after.
They dated for over four years, which turned them into a well-known couple in the Hollywood scene. Like all couples, they had their ups and downs. However, their downs seemed to make the headlines way too often. In 1999, Courtney Love practically ditched Edward in the middle of a fight and never returned.
Alyssa Milano and David Arquette
When you get into show business at a very young age you are bound to have at least one VIP relationship. Alyssa Milano was under the age of 20 when she began her romantic affair with David Arquette. Those were the shining days of "Who's The Boss?" for Milano and the days of "The Outsiders" and "Parenthood" for Arquette.
There was such a buzz covering these two back in the day that you might have thought there was a huge love affair going on between them. The truth is, their story lasted for just over 60 days, turning this romantic episode into a 60 minutes show.
Jon Bon Jovi and Diane Lane
Diane Lane is best known for her role in the 1979 movie, "A Little Romance." Only years later, she returned to the public eye with the 1989 TV series, "Lonesome Dove." Since then, she has captured our hearts in numerous roles and has left her mark in Hollywood.
During her 20s, she dated Jon Bon Jovi, who, in those days, did no more than sweep floors and write songs. It was only at the end of the 1 Nowadays, the man is happily married to the same woman (Dorothea Hurley) since 1989.980s that Bon Jovi became the Bon Jovi we know and love today.
Jennifer Grey and Matthew Broderick
Before Jennifer Grey put on her dirty dancing shoes, she starred in the 1986 huge teen hit "Ferris Bueller's Day Off," where Bueller was played by no other than Matthew Broderick. Funnily enough, in the movie, they played siblings who were always at each other's throats, but the sparks between the two were still there and undeniably so. However, they were kept secret for quite a while.
Their romance was revealed shortly before "Dirty Dancing" was released, and not long after, they decided to call it quits. The two have since had their fair share of much-publicized relationships: Broaderick with actress Sarah Jessica Parker and Grey with actor Clark Gregg.
Tatum O'Neal and John McEnroe
In the 1980s', John McEnroe was a professional superstar tennis player. He is known for throwing his temper on the tennis court, eventually leading to conflicts with the tennis association. Tatum O'Neal is a well-known actress who snagged an Academy Award when she was just ten years old.
When these two met back in 1986, he was at the peak of his career, and she was dealing with an illegal substance issue, which didn't stop them from getting married. They ended their marriage in 1994, which was followed by an ugly court case, accusations on both sides, and a 1980's story to be told.
Drew Barrymore and Edward Norton
Everyone says I love you, and everyone loves Drew Barrymore. How could you not? She has "adorable" written all over her face. Drew Barrymore and Edward Norton starred together in "Everyone Says I Love You" but only started to date a few years later. In 1999, Barrymore escorted Norton to the Acadamy Awards, and the stars were glowing for the two.
Their relationship didn't survive the welcoming of the new millennium, and before 2000 burst into the world, the two went their separate ways. Norton's way has led him to marry his current wife, Shauna Robertson, and Barrymore's way led her to two marriages and two divorces.
Kristen Johnson and Ryan Reynolds
Between 1999 and 2000, the sun shone for Kristen Johnson and Ryan Reynolds. Back then, Reynolds was making it big on "Two Guys and a Girl," and Johnson was doing the same while starring on "3rd Rock From the Sun". For a while, these two had it going.
People are always looking for spicy or interesting relationship stories but they won't be getting them from these two, who seem to have ended things on good terms. In recent interviews, both couldn't come up with any juicy stories about their past, but Kristen did say that Reynolds was a one-of-a-kind kind of guy, just not suited for her.
Sylvester Stallone and Brigitte Nielsen
During the 1980s, Sylvester Stallone and Brigitte Nielsen were one relationship that was always starring at the top of the headlines. Most of the gossip around them was based on rumors, but plenty of it was based on real-life issues the couple went through.
Nielsen, a Danish actress who appeared on the UK "Big Brother Show," and Stallone managed to preserve their marriage for less than two years, and in 1987 the two went their separate ways. Today they are both happily married — Stallone to Jennifer Flavin (third and current wife) and Nielsen to Mattia Dessì (fifth and current husband).
Winona Ryder and Johnny Depp
The indie couple of the early 90s, Johnny Depp and Winona Ryder were the black sheep of Hollywood. Both dark-haired beauties that took on some quirky films, their love seemed like a match made in heaven. The two met in 1989 at the premiere of Ryder's film "Great Balls of Fire!" — the classic biopic of the late Jerry Lee Lewis.
By the time they co-starred in "Edward Scissorhands" in 1990, the world was enamored by them. Constantly overwhelmed by the press, the public pressures weighed on their relationship. Eventually, they gave in and, by 1993, decided to end it.
Heather Locklear and Tommy Lee
If you're from the 1980s', you probably remember Heather Locklear from "Dynasty". If you're from the 1990s', you are obviously a "Melrose Place" lover. Either way, Locklear was on top of the list, making her an icon of those decades. Tommy Lee was the Mötley Crüe drummer, and in 1996 they both tied the knot.
After him being unfaithful to her, they divorced in 1993, which allowed her to marry Richie Sambora, and allowed him to marry Pamela Anderson (and later Britney Furlan). It looks like Locklear has a thing for musicians, and Tommy Lee, for sure, has a thing for blondes.
Cameron Diaz and Matt Dillon
"A Kiss Before Dying," "Singles," and "There's Something About Mary" are only some of the movies Matt Dillon is recognized for. He might have been happily (or not so happily) married in the movies he starred in, but in real life, the facts are slightly different.
1995 was the year for Matt Dillon and Cameron Diaz, who was at the highlight of her career at the time. The relationship lasted for three years, and the two decided to break up in 1998. Rumors say Cameron wanted to take the next step in life together with Dillon. He, however, was nowhere near.
Jerry Hall and Mick Jagger
Models and rockstars go hand in hand like burgers and fries. Just ask these two. In 1991, lead singer and one of the founder members of The Rolling Stones, Mick Jagger, and actress-model Jerry Hall married in exotic Bali, Indonesia.
However, eight years later, their fairy tale marriage ended after Hall discovered that Mick had been unfaithful to her, which ended up with the third party bearing a child. It seems that as one of the most influential figures in rock and roll, you have one too many temptations. Jagger has fathered eight children with five women. Jagger, stick to music!
Lenny Kravitz and Lisa Bonet
Last century (ugh, we know it's technically true but we still get the creeps when we see those words in that context), Lisa Bonet was making it big as Denise Huxtable on "The Cosby Show," while Lenny Kravitz was making it big as a musician.
To us, they always seemed like the perfect match; however, things were not all stable for the two. They married not long after they met and divorced not long after they married. They had a daughter together, which will keep them in some ways together for as long as they live, whether they like it or not.
Sheryl Crow and Owen Wilson
The country, jazz, pop, and rock star Sheryl Crow has dated a few big names; the famous Eric Clapton is one of them. She never really settled down with anyone and never bore children of her own. She has, though, adopted two boys who she brings up alone.
Back in the 199os', Crow had an on-and-off relationship with Owen Wilson that ended not much longer after it started. Wilson is known for his unsteady ways when it comes to relationships, so the ending of this little romance story didn't come as a surprise to us. He later went on to have three children with three other partners.
Tom Cruise and Rebecca De Mornay
1983 was the year for Rebecca De Mornay and Tom Cruise. They were both working on the set of "Risky Business" at the time, which turned into a real-life romance. Apparently, while they were shooting the movie, Rebecca was already involved with Harry Dean, but this didn't stop her from starting a new relationship with Cruise.
By 1985, the story between the two was over. Tom Cruise had an amazing career in front of him, with "Top Gun" being the biggest success of those days, and Rebecca De Mornay went on to star in numerous movies, such as "The Three Musketeers," and "The Hand That Rocks The Cradle."
Gwyneth Paltrow and Ben Affleck
This story has somewhat of a circular structure: Ben Affleck and Gwyneth Paltrow met on the set of one movie and then had to meet again, after they had already broken up, to promote another movie. That, in itself, already sounds like a movie.
They first fell in love in 1998's "Shakespeare in Love," and by the time their 2000 flick "Bounce" came out in the year 2000, they were already apart. Gwyneth was quoted saying that Ben isn't the type of boyfriend you marry, but the one you date to heal childhood trauma. We don't know if that's a compliment or not.
Melissa Gilbert and Rob Lowe
Mellisa Gilbert spent most of her childhood years on the little prairie, so no wonder she fell madly in love with mega babe Rob Lowe when she first met him. We doubt it if there were charmers like Lowe on the prairie. Gilbert and Lowe went out for over six years, with a few breakups along the way.
At one stage, they got engaged, but that never led to a wedding. Rob carried on with his life, spreading his charms on other women, and Melissa nourished her career, became a producer and politician, and is happily married to Timothy Busfield.
Emilio Estevez and Demi Moore
Before starring as Andrew Clark, the athlete in "The Breakfast Club," Emilio Estevez was introduced to the stunning Demi Moore (who was still before her "Indecent Proposal" and "Ghost" days). They dated for a while and got engaged but never tied the knot.
They were both madly in love with one another, but apparently, that was not enough for Estevez to not play the game with another woman simultaneously. When Demi's therapist advised her not to take it any further with Emilio, she knew they had to go separately. But other relationships were not too far ahead for either of them.
Tyra Banks and Seal
In the 1990s, Seal was one of the biggest stars around, with his greatest hit, "Kiss From a Rose," winning several awards at the time. Seal is better known for his relationship with Heidi Klum (which was highly publicized but famously ended in a divorce), but before then, another supermodel was on the scene.
Seal and Tyra Banks dated for three months. Their relationship was kept relatively low-key, and besides one event that they appeared together, no one made a fuss of them. In fact, other than Seal's marriage to Klum, both stars' love life didn't make too many headlines.
Corey Feldman and Drew Barrymore
The child stars of the 1980s were very different than the ones of today. Back then, if you appeared in one movie, you probably appeared in them all. During his teens, Corey Feldman starred in "Friday the 13th", "Gremlins," "The Goonies," and the all-time classic, "Stand by Me."
In 1989, Feldman dated Drew Barrymore, also known as a child star of those days. It's actually kind of sweet when you think about it — they were probably the only people who could fully understand each other. The two came together as an item to the Oscars that very same year.
Kate Moss and Johnny Depp
Johnny Depp and Kate Moss were quite an item for a hot minute. And by hit minute we mean about four years, between 1994 to 1998. In 2007, Johnny Depp was interviewed speaking fondly about Kate Moss, which would have made you think Moss and Depp had it going really well at the time.
Well, the truth is that it wasn't all that good. Their relationship came after Depp's love story with Winona Ryder, which became a huge story within the Hollywood tales and lasted for just over three years. All parties involved went on to have other high-profile relationships.
Cher and Tom Cruise
The iconic Cher can get away with almost anything. When she was a 38-year-old lady, she got away with dating a 22-year-old young man by the name of Tom Cruise. Now, we aren't really sure what they mean when they say "get away with" in this context. It's not like people (let alone people in Hollywood) get punished for a relationship with an age gap.
He was just taking his first footsteps in the Hollywood world, while she had already built her reputation as a successful singer. The two dated for a while, not turning their story into something great. They were busier smiling to the cameras than actually trying to make something work.
Gary Oldman and Uma Thurman
Uma Thurman is one you just gotta love. And Gary Oldman thought that, too, back in the 1990s. Oldman was Thurman's first true love, as she once said in an interview. She said she was a young and inexperienced woman involved with a man twelve years her senior.
She also said that it isn't a surprise that their relationship ended when it did — less than two years after they tied the knot. Uma even took it a step further by adding that this was the mistake of her life. He was 12 years older than her, and what was done has been done.
Madonna and Vanilla Ice
The queen of pop dating the king of ice cream. What a strange couple they were. There was a slight age gap between the two, and according to Vanilla's story, she taught him many things he didn't know about relationships.
They dated for just under a year and broke up because Vanilla Ice didn't approve of the book she released at the time, which exposed him in a disrespectful way. Now, we ask you, Mr. Vanilla, it is known that the queen says whatever is on her mind, anywhere, anytime, and about anyone. What exactly did you expect when you started to date her?
Tom Cruise and Nicole Kidman
You might have thought this golden oldie wouldn't get a mention on this list. But how could we forget the Nicole Kidman-Tom Cruise love story? Kidman met Cruise in 1989, during the filming of "Days of Thunder," and from her dating history, it seems she may have a thing for guys who are shorter than her.
On Christmas Eve of 1990, Kidman and Cruise got married. It was Cruise's second marriage at the time. They even adopted two children, Isabella Jane and Connor Anthony, while they were married. In 2001, the couple split. Cruise filed the divorce. In 2006, Kidman admitted that she still loved Cruise dearly, and it wasn't easy to totally erase him from her life.
Molly Ringwald and Anthony Michael Hall
Molly Ringwald and Anthony Michael Hall are the perfect examples of "when a beauty dates a geek." They both starred in the 1980's movies, "Sixteen Candles" and "The Breakfast Club," and dated for a short while after making these hits. These were 80s idols that were adored by teenagers all over the world who loved to see them together.
The fans grew up, and so did the stars, each going their separate way but remaining good friends until this day. Nowadays, Ringwald is married to American writer Panio Gianopoulos and shares a daughter with him. Hall is married to actress Lucia Oskerova.
Richard Gere and Cindy Crawford
In 1987, Richard Gere already had a resume of women he had dated, which listed, amongst others, Kim Basinger, Priscilla Presley, and a few other big names. He was the stud to end all studs. Stunning Cindy Crawford was only in her early twenties when she met Mr. Gere, which led to the two marrying in 1991.
Crawford didn't want to waste her precious twenties with the silver fox and decided to untie the knot. She was one of the hottest women alive during the 1990s, and he was, and still remains, a true charmer any woman would love to have.
Kim Basinger and Prince
The movie "Batman," which was screened in 1989, was where it all began for Kim Basinger and musician Prince. Basinger starred in the movie, while Prince was responsible for the amazing soundtrack. Kim Basinger was interviewed once, and she said very freely that the time with Prince was very meaningful for her, as all moments were back then.
She was a free spirit who did whatever was on her mind, and judging by Prince's public image, he was very similar to her in that respect. Apparently, dating Prince was right up her alley. The two even worked together on music projects!
Winona Ryder and Christian Slater
It is no surprise that this romantic story took its first steps on set. It happened to many stars, and it happened to Christian Slater and Winona Ryder too. Slater and Ryder starred together in the 1988 movie "Heathers" and had a massive crush on one another, so it's a good thing they played a couple.
They announced publicly that they were an item, even though their relationship didn't last too long. Winona Ryder said that Slater was just another story to add to her relationship book. Slater, however, admits that Winona was the love of his life and the woman he always wanted.
Reese Witherspoon and Ryan Phillippe
Where would we be without the ultimate '90s rollercoaster romance between Reese Witherspoon and Ryan Phillipe? The pair met when Ryan crashed Reese's birthday party. He turned out to be a very welcomed uninvited guest!
In 1999 they went on to star as doomed lovers in the cult classic "Cruel Intentions" and got hitched a few months later. After rumors and suspicions of Ryan allegedly playing around with other women, Phillipe and Witherspoon called it quits. They have two children together — a daughter named Ava and a son named Deacon, who they continue to happily co-parent to this day.
Brooke Sheilds and Liam Neeson
Despite their 13-year age gap, Brooke Sheilds and Liam Neeson hit it off in late 1991. Their love connection was so intense that Neeson popped the question after only 3 months of dating! However, shortly after the proposal, Liam flew home to deal with his home flooding.
Brooke apparently patiently waited to hear from her fiance but never did. Yep, he ghosted her! Even Brooke Shields can get ghosted, apparently. No one is safe anymore. A few months later, when he got his senses back, he came crawling back to her and re-proposed, to which Sheilds answered, "NO." Go, Brooke!
Lance Bass and Danielle Fishel
"Boy Meets World" star Danielle Fishel and NSYNC member Lance Bass were high school sweethearts back in the 90s and even went to prom together. The young lovers weren't meant to be but remained good friends. After Lance came out as gay in 2006, Danielle was incredibly supportive of her former flame.
Lance recently told Danielle, "I always knew you would completely accept me," on his podcast "The Daily Popcast with Lance Bass." Now that's love! The two eventually found romance in other partners — Bass is married to actor Michael Turchin and Fishel is married to film producer Jensen Karp.
Ellen DeGeneres and Anne Heche
Just mere days before Ellen DeGeneres's iconic "InStyle" magazine cover where she announced to the world that she was gay hit the stands, she met the late actress Anne Heche at the 1997 Vanity Fair Oscars Afterparty. It was an instant connection and very soon the two skyrocketed into being the most famous queer couple in Hollywood at the time.
Unfortunately, their relationship ended a few years later when Heche apparently left Ellen with no explanation. In a 2001 interview with the "Los Angeles Times," Ellen admitted, "I'm left with everybody else wondering what happened...I feel betrayed." Talk about being blindsided!
Matt Damon and Minnie Driver
1997 was a great year for Matt Damon. Not only was his critically acclaimed film "Good Will Hunting" released (for which he would later win an Academy Award for best screenplay) but he also found love. Matt and Minnie met on the set of the film and started dating.
However, any good will (pun absolutely intended) between the two fizzled out when Damon broke up with Minnie by announcing to the world that he was single on "Oprah." Millions of viewers, including Minnie herself, were shocked by the announcement! Not a cool move, Matt. We wonder what Luciana, his current wife, has to say about it.
Notorious B.I.G and Faith Evans
In a whirlwind romance, the iconic rapper, the late Notorious B.I.G. (also known as Biggie Smalls) met musician Faith Evans on the set of a photoshoot in 1994. A mere eight days later — yes eight days — the two were married! These two knew how to move quickly!
Reportedly, while the romantic relationship between the two began to fizzle out, they remained friends. They even welcomed a baby boy into the world in 1996. Unfortunately, the rapper never got to enjoy being a father for too long as he was killed a mere six months after his son's birth.
David Spade and Kristy Swanson
It is no secret that Spade is more celebrated for his humor and comedic work than he is for his physical appearance, but that has not stopped him from dating some of the most attractive women in the industry. In fact, the "Saturday Night Live" alum and comedian has a rather lengthy list of former flames.
One of the first on the list is actress Kirsty Swanson. Spade and Swanson met on the set of the 1996 film, "Heads in a Duffel Bag." With a title like that, it's no wonder the film bombed. However, love blossomed between the stars which lasted for almost a year.
Joaquin Phoenix and Liv Tyler
It seems that Live Tyler really believes in love at first sight! In an interview with "The Morning Call," Liv revealed that, "I fell in love with Joaquin the second I saw him" on set for the 1997 film "Inventing the Abbots." Sadly, their romance only lasted for three years until the pair split.
It's alleged that Liv was more dedicated to the relationship than he was. Whatever the case may be, they remain friends. According to Tyler she doesn't fall in love very often. She has, however, had two more serious relationships after Phoenix. Phoenix is currently in a relationship with actress Rooney Mara.
Ted Danson and Whoopi Goldberg
While on the set of the 1993 film, "Made in America," Ted Danson and Whoopi Goldberg started a romance that has since been dubbed "the affair that cost Danson $30 million." Quite the title. Ted Danson had been married to his wife Casey Coates for almost two decades when he and Whoopi ignited their surprising romance.
Once the secret was out, Coates filed for divorce which ultimately cost Danson a cool $30 million as well as a butchered reputation. After a year and a half, Whoopi and Ted called it quits in an anything-but-amicable breakup. Was it all worth it?
Michael Keaton and Courteney Cox
The year was 1989. Before Michael Keaton donned the Batman suit and before Courteney Cox was having coffee with her friends at Central Perk, the pair met and fell in love. After six years together, and rumored potential engagement, Keaton and Cox called it quits.
The two went their separate ways and got married — Cox married David Arquette and Keaton married Caroline McWilliams. While it's never been revealed what caused the breakup, Courteney admitted to "People" magazine in 1995 that "We still love each other." Considering they are both divorced now, could there ever be a comeback? We sure hope so.
Salma Hayek and Ed Norton
There are so many Hollywood couples who met while working together on one set or another. But apparently, there are more ways for celebrities to be introduced to each other. Who needs Cupid when you have a chiropractor? Yup, Hollywood royalty Selma Hayek and Edward Norton met through their mutual chiropractor in 1999!
Turns out he or she really had the couple's backs...Ha Ha Ha. The private pair dated for a few years until parting ways in 2003. While the cause of the split has never come to light, Hayek and Norton still seem amicable, even attending each other's weddings.
Thurston Moore and Kim Gordon
Thurston Moore and Kim Gordon were the ultimate romantic Rock and Roll royalty. The two musicians met, fell in love, and formed the iconic band Sonic Youth back in 1981. Moore and Gordon even tied the knot in 1984 making them the coolest married couple in the music industry at the time.
Unlike a love song, the rockers' relationship untimely turned very sour. It turned out that Thurston was secretly seeing his book editor Eva Pinz. Kim discovered the truth when she noticed suspicious texts on Thurston's phone. Sonic Youth imploded and the couple's relationship ended in a messy divorce.
Spike Jonze and Sofia Coppola
It seems that the band Sonic Youth was a hotspot for romance. Not only did former flames Thurston Moore and Kim Gordon form the band but directors Spike Jonze and Sofia Coppola met on the set of Sonic Youth's music video "100%."
What was first a formidable friendship soon blossomed into a romance that led the two to say their vows at Sofia's famous father's (Francis Ford Coppola's) vineyard in 1999. Sadly, Coppola and Jonze sadly split up a few years later. Some have even speculated that Sofia's film "Lost in Translation" drew inspiration from her strained relationship with Jonze.
Carson Daly and Jennifer Love Hewitt
If you were a TRL-loving teen, then you know all about the iconic relationship between MTV star Carson Daly and 90's actress Jennifer Love Hewitt, star of "I Know What You Did Last Summer." The two got together in 1998 and were so loved up that Daly went and got a tattoo of Jenniffer on his leg! Talk about a commitment.
As we all know, relationship tattoos often jinx a relationship. Carson and Jennifer called it quits. While the two remain good friends, Carson was shocked to discover the news of his break-up from "E! News" and not from Jennifer directly.
Fiona Apple and Paul Thomas Anderson
In 1997, songstress and indie music princess Fiona Apple and Director Paul Thomas Anderson were regarded as the ultimate 90s power couple. Not only was the pair a love match, but they collaborated on various projects together. Fiona lent her musical talent to Paul's film "Magnolia," while Paul directed four of Fiona's music videos.
What an idyllic portrait of the life of a couple of artists! Unfortunately, after four years, the relationship fizzled out. Fiona has since spoken out about the high pedestal the media put the relationship on and has revealed that the relationship had many negative and toxic elements.
Brad Pitt and Jennifer Aniston
Possibly THE It Couple of the 90s (and yes, the early 2000s) and America's sweethearts were, of course, Brad Pitt and Jennifer Aniston. One of the most famous celeb couples in Hollywood history began in a rather ordinary way. The pair was set up on a date by mutual friends. The rest was pop-culture history.
The end of Brad and Jennifer's marriage marked the beginning of a tabloid tsunami that would last years of rumors and gossip surrounding the failed romance. The two re-ignited rekindled romance rumors when spotted being very supportive of one another during the 2021 awards season.
Bruce Willis and Demi Moore
Talk about a whirlwind romance! Demi Moore and Bruce Willis first laid eyes on one another in July 1987 when... ahem... Demi was still involved with another man. She was engaged to Emilio Estevez at the time. It didn't take long for Demi to end her engagement with Estevez and jump head-first into a relationship with Bruce.
A mere five months after the first meeting, the two eloped in Las Vegas (how original). For a long time, they were one of the most high-profile couples in show business. However, After giving birth to three daughters and ten years of marriage, Moore and Willis divorced.
Gwen Stefani and Gavin Rossdale
In a burst of magical music match-making, Gwen Stefani's band, No Doubt, opened for Gavin Rossdale's band, Bush, in 1995. The songbirds quickly became love birds, and after a six-year relationship, the two got married! Sounds like a classic story. We're sure it can be made into a musical in a heartbeat. However, it didn't last.
Things seemed to be peachy for the pair, who then welcomed three children into the world. However, after it became apparent that Gavin was engaging in some...extra-marital activities with the family nanny...yawn... The two soon got divorced, and Gwen has since moved on with country crooner Blake Shelton.
David Bowie and Iman
One of the most successful showbiz couples has got to be David Bowie and Iman. While they had both been married, it seems that their love for each other was bigger than anything they had experienced before. The power pair were together for 26 years before Bowie's untimely passing.
The two first locked eyes on one another in 1990 at a dinner party. In an interview with "Hello Magazine," Bowie said, "My attraction to her was immediate and all-encompassing... That she would be my wife, in my head, was a done deal.” *Sniff* Can someone pass us the tissues, please?
David Copperfield and Claudia Schiffer
Some call it love, and some call it magic. Famous magician and illusionist David Copperfield managed to woo supermodel Claudia Schiffer by asking her for assistance during one of his shows in 1993. Would you look at that, apparently, magic tricks can, in fact, get you a girl! A year later, the two were engaged!
However, the engagement would never bloom into a marriage. The pair split up in 1999. What's particularly peculiar about the pairing is the controversy that surrounded it. Many have speculated that the relationship was a long ruse in order to boost Copperfield's fame. However, both Schiffer and Copperfield strongly deny this. Hmm...
Goldie Hawn and Kurt Russell
It's not unusual for co-stars to canoodle; however, what is unusual is for the canoodling to last for over 30 years. That happens to be the case for the loved-up pair Goldie Hawn and Kurt Russell. The two ignited their long-lasting relationship flame while on the set of the 1983 film "Swing Shift."
The two have welcomed a son named Wyatt as a sibling to Goldie's Kate and Oliver from her previous marriage to Bill Hudson. While all three children have the acting bug, it's pretty clear that Kate Hudson has garnered the most fame and success. When asked about the key to the pair's relationship success, Goldie credits the two for never marrying and having time to themselves.
Christie Brinkley and Billy Joel
In a meeting that would only be possible for the rich and famous, music icon Billy Joel and supermodel Christie Brinkley met while on a luxurious vacation in the Caribbean in 1983. How fancy! The piano man himself used his musical talents to woo his future wife.
Joel played the piano on the island where Brinkley and her group were vacationing, and the rest is history! It seems that the couple had a love for the sea as they tied the knot on a super yacht two years later. Sadly, due to busy schedules and failed communication, the pair divorced.
Pamela Anderson and Tommy-Lee
One of the most infamous couples of the 90s was undoubtedly Pamela Anderson and Tommy Lee. The two had a rather off-beat first encounter. After locking eyes at a New Year's Eve Party in 1994, Tommy Lee licked Pamela's face. Apparently, that swept her off her feet!
In what only can be described as a whirlwind romance, Tommy and Pamela were married only days later! Unfortunately, the pair's private love life became tabloid fodder which ultimately lead to their marriage breaking down. The two share two sons — Brandon and Dylan — both of whom are making their way in entertainment.
Hugh Grant and Elizabeth Hurley
As costars do, Hugh Grant and Elizabeth Hurley met and fell in love on the set of the 1987 film "Remando al Viento." The couple was together for an impressive 13 years (which may as well be 50 years in Hollywood time). If England hadn't already had actual royals, these two could definitely fill in that spot.
However, the relationship was far from perfect. Hugh was caught in a rather compromising position with a... let's call her a lady of the night... in 1995. Despite the shock and hurt on Hurley's part, the two stayed together for another five years before finally ending their relationship.
Melanie Griffith and Antonio Banderas
It's not surprising, given all the glamourous stars in attendance, that Hollywood award shows make for a great opportunity to meet your future lover. After all, that red carpet is right there and it's full of attractive people looking their absolute best. This was the case for Antonio Banderas and Melanie Griffith.
Banderas first saw Griffith at the 1989 Academy Awards and fell in love. Griffith was still married to Don Johnson at the time. It was only six years later, while co-starring in the 1995 film "Two Much", that the pair (who were...ahem...both married at the time) got together. Well, the pair lasted together until 2014, when they eventually split.
Jude Law and Sadie Frost
Before the tumultuous tabloid headlines surrounding Jude Law and Sienna Miller, there was Jude Law and Sadie Frost's relationship. Law and Frost met on the set of the film 1992 film "Shopping." While Frost was married to Gary Kemp at the time, she admitted in her biography "Crazy Days," "The force of the love I felt for Jude and his intense ambition made me feel out of control."
The two got together and eventually got hitched in 1997. Jude's career skyrocketed at the time, which added great strain on the already rocky relationship. Frost eventually filed for divorce in 2013.
Busy Phillips and Colin Hanks
Unlike most celebrity couples, Busy Phillips and Colin Hanks did not need the entertainment industry to put them together. There were no movie sets or award shows in their meeting story. The two met and started dating in college in 1997. The love between the two blossomed while they were both attending Marymount University.
Despite breaking up a few years later, the two have only had good things to say about one another over the years. The two remain such good friends that they've made several talk show appearances together over the years and their children (from separate relationships) even go to the same school!
Alec Baldwin and Kim Basinger
Ah, yet another loved-up co-star couple! Alec Baldwin and Kim Basinger met on the set of the 1990 film "The Marrying Man" and ignited their fiery relationship. As if the name of their film was a premonition for their future, Basinger and Baldwin were married a mere six weeks after first getting together.
Unfortunately, their love wasn't built to last. Basinger filed for divorce from Baldwin eight years after tying the knot. They famously have one daughter together — Ireland Baldwin, who has been enjoying quite an established career in the industry as a model, actress, and social media personality.
Chloe Sevigny and Harmony Korine
Ah, young love! Before Chloe Sevigny was an acclaimed actress and Harmony Korine a cult-classic director, the pair were just friends in their early teens. When it came time to cast actors for his first film, "Kids", Korine turned to Sevigny. Once the film was completed in 1994, the pair became more than just friends and co-workers.
Sevigny and Korine embarked on an on-again-off-again relationship that lasted several years but finally ended in the early 2000s. Since then, both of them have found true love — Sevigny is now married to an art gallery owner named Siniša Mačković, and Korine is married to former actress Rachel Simon.
Julia Roberts and Lyle Lovett
In a relationship that no one saw coming, Julia Roberts and Lyle Lovett had a whirlwind romance in 1993. The pair got hitched only three weeks after dating! Three weeks is usually enough time to finish a book (depending on the book) or go on a really fancy vacation. They are hardly enough time to decide you want to spend the rest of your life with a person.
The writing was on the wall when Lovett admitted in an interview with "People Magazine" that before tying the knot, "we’d never spent more than seven days together.” After two years of marriage, the relationship fizzled out and ended in divorce.
John Cusack and Jami Gertz
Back in the 1980s and 1990s, John Cusack set the standards for all men in the industry. Apparently, not only was he an inspiration for other men, but he was also very popular amongst women. Take Jami Gertz, for example. Gertz was a member of the famously known "Brat Pack" of the 1980s, and the two had things going around 1983.
They met on the set of "Sixteen Candles," and before it even began, the romance was already over. Cusack has since moved on to other relationships, though he has been extremely private about all of them, and Gertz went on to marry philanthropist Tony Ressler.
Jay Leno and Sharon Osbourne
Wait, what? Hasn't Sharon Osbourne been married to Ozzy since the dawn of time? Well, apparently she hasn't. Just like anyone else, she has her own history, though hers is arguably cooler than most. Before Sharon Osbourne was titled the First Lady of Rock&Roll, she had a short affair with Jay Leno.
Yes, THE Jay Leno. They met by coincidence at a bar and had a little fling. As it turns out, Osbourne didn't take the whole thing too seriously. Two months after they had their fling, Leno introduced his now-wife, the love of his life, to Osbourne, making the whole fling — history.
Chris O'Donnell and Reese Witherspoon
In 1993, Chris O'Donnell was 22 years old, and Reese Witherspoon was barely 16. She accompanied O'Donnell to a tribute party following his appearance in the movie "Scent of a Woman" and if anyone ever looked like the dictionary definition of the term "baby face", it has to be these two.
There was a bit more going on than just accompanying one another. Chris O'Donnell had reportedly admitted at the time that he had a soft spot for Whitherspoon and thought she was very nice. She, on the other hand, never spared a compliment and said that they were just friends.
Emilio Estevez and Paula Abdul
Emilio Estevez, known to most of us as the star of "The Breakfast Club" and "Young Guns," met Paula Abdul in 1991. They married just one year later, in 1992, and by 1994 the couple was already divorced. Well, that's the short version of it, at least. We are sure that each of them has a whole narrative to spill.
In one interview, Abdul said that their relationship ended because she wanted to have children. Emilio, who already had two children from a previous relationship, wasn't interested, leaving the two devastated and heartbroken. While she did get married after that, she has never had children.
Jennifer Garner and Scott Foley
Jennifer Garner met Scott Foley in 1998 when they were shooting "Felicity." Garner played Foley's girlfriend and, as so often happens for actors, ended up falling madly in love with him, for real. In 2000 they were married and, in 2003, divorced.
They both believe that their marriage never made it because they see themselves as "Hollywood victims." Everything is done in seventh gear, everything is instant and done in the heat of emotions, so it is not surprising that so many couples break up. Garner famously met her next husband, Ben Affleck, on a movie set too, and while their marriage lasted longer than her first, they eventually divorced.
John Cusack and Melissa Gilbert
In a turn of events, these two got involved in what looks like a classic game of jealousy, guilt, and emotional tugging. So, the little girl from the little prairie supposedly used Cusack to get back at Rob Lowe, who she dated for almost six years prior to bumping into Cusack.
Just one important detail: Lowe was Cusack's best friend at the time. She admitted this happened and excused it by saying that this was her own personal way of dealing with a broken heart and John just happened to be at the right time but in the wrong place.
Jennifer Love Hewitt and Will Friedle
When Jennifer Love Hewitt and Will Friedle were just 18 years old, they played best friends on the set of the movie "Trojan War", and we have a feeling you know where this is going to go but we will tell you anyway. The two kicked off a true love relationship from there on.
Later on, Hewit would play one of Friedle's love interests in "Boy Meets World." The relationship between the two on set was far more interesting than what was going on in reality, and the couple split up not long after they became publicly known as an item.
Denise Richards and Paul Walker
The late Paul Walker made it big when he starred in the movie "Tammy and the T-Rex" alongside Denise Richards. Now, he didn't succeed because of how great the movie was but because of what followed. He hit it off with one of the biggest names in the industry at that time.
Obviously, you can't just put these two beautiful creatures in the same room and NOT expect something to happen. These were the mid-1990s, and Denise Richards was one of the most beautiful and desirable women around. They were a ridiculously stunning couple who enjoyed the limelight for a good while.
Joey Lawrence and Keri Russell
Way before he became one of our most hated yet loved characters on "Felicity," Joey Lawrence was busy galavanting with Keri Russell down the streets of Hollywood. Their short relationship lasted for just under six months and had its share of drama.
As it turns out, while Russell was involved with Lawrence, she was still in an on-and-off relationship with the ex-boyfriend Tony Lucca of "The Mickey Mouse Club." The two have since tried their hand in marriage (to other people, of course), in divorce, and in parenting. Lawrence is currently married and Russell is in a relationship with another co-star, Matthew Rhys.
Fred Savage and Jennifer Love Hewitt
Fred Savage gained immense popularity in the late '80s and early '90s for his role as the lead in "The Wonder Years." At the same time, Hewitt was 14 and making a name for herself on Disney's "Kids Incorporated." The two young stars eventually crossed paths.
In an Instagram Live interview with TooFab, Hewitt reminisced about crushing on Savage. She revealed that for their first date, Savage took her to the Laugh Factory for a comedy show. Unfortunately, their love story was short-lived because of Hewitt's unusual pet: a pig. She said she never saw him again because he was really creeped out.
John Cusack and Lili Taylor
John Cusack and Lili Taylor starred together on "Say Anything." As it turns out, Taylor wasn't satisfied with only dating Cusack, as it was reported that she had a bit on the side with D.V. DeVincentis, one of Cusack's best friends at the time. Though they probably didn't stay friends after that.
In 2000 Taylor and Cusack starred together again, this time in the movie "High Fidelity." How ironic, considering how their previous relationship ended. The affair between the two never skyrocket, and maybe that's a good thing when you think about the uncomfortable events that made them go their separate ways in the first place.
Liam Neeson and Helen Mirren
This might come as a shock to you, but during the 1980s, the queen of the Oscars dated the king of the screen for almost five long years. Neeson and Mirren met playing the roles of Gawain and Morgana on the set of "Excalibur" when they were still both unknown.
They lived together, loved one another deeply, and admitted that, at the time, they were considered a serious item. Mirren confessed that the two broke up because Liam had difficulty being under Helen's shadow. If only he would have realized that such a great actor could never be under anyone's shadow.
Justin Timberlake and Fergie
Before NSYNC became NSYNC, the pop girl group Wild Orchid was a big thing, and Justin Timberlake and Fergie had it going. They were both in the entertainment industry from a young age, which is probably what drew them to one another. Timberlake was just 16 years old, and Fergie was seven years his senior.
Age was never a barrier until Britney came along. They have since both had high-profile relationships. Fergie married actor Josh Duhamel, had a son with him, and then the two got divorced. Timberlake is currently married to actress Jessica Biel, and they now share two kids.
Charlie Sheen and Robin Wright
Notoriously a bad boy, every single relationship that Charlie Sheen has been involved in reached the tabloids and the headlines. Except for one. Not much is known about his short affair with Robin Wright, and we are here to tell you all about it.
Sheen and Write had a sweet teenage romance that went on from 1981 until 1982. Sheen was 16, Write was 15, and they two were both in high school. This obviously explains why the press wasn't in on it when the two were an item. Since then, the two have dated many other Hollywood stars, enough to fill up another list.
Juliette Lewis and Brad Pitt
Before he became an A-lister, before his Hollywood royalty days, and before "Thelma and Louise," Pitt dated his co-star at the time, Juliette Lewis. She starred alongside him in "Too Young to Die?" and they were together for just over four years, despite a significant age difference between them.
In 1993 the couple decided to go their separate ways. They had an innocent love affair that would probably never survived if they would have met at an older age. Lewis married (and divorced) professional skateboarder Steve Berra, and Brad became Brad Pitt and had a lot of women to date.
Lisa Kudrow and Conan O'Brien
It is Conan O'Brien who we must thank for turning Lisa Kudrow into Lisa Kudrow (and Phoebe). As it turned out, Kudrow met O'Brien at an improv comedy class, and as soon as she set her eyes on him, she fell madly in love. Honestly, these two make such sense together that we're surprised we couldn't guess their history with each other.
The two dated for a while until they realized that a great sense of humor on both sides was not enough to keep the two together. O'Brien was the one who encouraged Kudrow to follow her dream and become an actress. And what a great job he did.
John Cusack and Janice Dickinson
The romance between John Cusack and Janice Dickinson was intensive and wild. Or, at least, that is what the papers said when they discovered the two were getting romantic with each other. The two were seeing each other a little after Cusack ended his story with Claire Forlani and before he had a short fling with Melissa Gilbert. What a busy guy.
It was reported that the two were caught while playing adult games in an airplane restroom. Hey, when they say "get a room" this isn't the kind of room they mean. Dickinson claimed that Cusack had no sense of humor and that she found him pretty dry.
Jessica Simpson and Jensen Ackles
Jenson Ackles was Jessica Simpson's first love and the first guy to give her a broken heart. In 1998, when Simpson was just 18 years old, she dated the "Supernatural" star, Jensen Ackles. Not long after, their romantic love affair in life would turn into a horror movie, for Simpson at least.
It took Simpson a long time to get over Ackles. The poor thing. On one episode of "Newlyweds," Simpson told her ex-husband Nick Lachey, that she was devastated after the breakup with her first love. She never mentioned the name, but it was obvious who she was referring to.
Jon Hamm and Jennifer Westfeldt
The love story between Jon Hamm and Jennifer Westfeldt began in the late 1990s and lasted almost two decades. They first met in 1997, way before Westfeldt starred in "Kissing Jessica Stein" and before Hamm found himself on the set of "Mad Men."
Jon was a party animal who enjoys the big and ravishing Hollywood parties, while Jennifer was the stay-at-home kind of girl, so they were destined to eventually go their separate ways. Really, people? You're together from 1997 to 2015 and THIS is the thing that finally comes between you? Anyway, Hamm is now engaged to actress Anna Osceola.
Robin Thicke and Paula Patton
We know that the love story between Robin Thicke and Paula Patton happened before either of them turned 20. We can only assume that what was going on between them was pure puppy love, but who would have believed these two were together for 21 years?
These were the early 1990s; they fell in love and were by each other's side through thick and thin. Or, shall we say, Thicke and thin? Until 2014 when they realized 21 years was more than enough. While we are unaware of any current partner Paula may have, Robin is currently with model April Love.
There are those incredibly high-profile celebrity couples out there like Beyoncé and Jay-Z, Blake Lively and Ryan Reynolds, Kanye, and Kim (at least they were), and a bunch more. But then there are the couples that make you go, "Wait, what?" You are not alone. We found it hard to believe they were once (or still are) together too.
These stars are huge in their own right, but when it comes to their love lives, they have managed to keep things under wraps. Either that, or the world seems just seriously underwhelmed by their romantic choices. Here are all those celeb couples who you barely see photographed together.
Emma Stone and Dave McCary
Emma Stone ("La La Land" and "The Amazing Spider-Man") and "Saturday Night Live" writer Dave McCary have been extremely private about their relationship. They met at the SNL studio in 2016. That was the third time, you may recall, that Emma Stone hosted. This time, McCary directed, and by the end, the two connected. Not a peep for two years.
Since their public engagement announcement on Instagram in March 2021, they had their first baby girl. Being relatively private, Emma and Dave are not seen publicly very often, making us check online every now and then for their relevant statute.
Carey Mulligan and Marcus Mumford
This couple has been so low-key that few know they have been married since 2012. Carey Mulligan told "Vogue" a few years ago that the Mumford & Sons singer was hers, and she didn't want to share. But their story is too adorable to keep quiet. Mulligan met Marcus Mumford at church camp when they were kids.
They kept in touch by post for years, keeping things traditional. When the former pen pals ran into each other again at a party in 2011, a romance sparked. They tumbled into love with a flurry of love letters. Now, they share two children.
Ryan Gosling and Eva Mendes
When someone told Eva Mendes that she ought to get out more with hubby Ryan Gosling, she replied, “I’m good. Rather be home with my man than anywhere else in the world.” And that’s where they’ve stayed, apparently. We didn’t even know the couple was having a baby until their first daughter was born.
They met in 2011 on the set of the film "The Place Beyond the Pines." They were spotted together on the red carpet at the Toronto International Film Festival and at the New York City premiere of the film. And that’s pretty much it. They are very rarely caught together in public.
Cameron Diaz and Benji Madden
We know with certainty now that Cameron Diaz and Benji Madden began dating in May 2014. There was a lot of speculation until, in July of that year, Nicole Richie (married to Benji Madden’s twin brother and bandmate) spilled the deets, and their secret was no longer their secret.
She confessed to introducing the couple and revealed that they were, in fact, in love. By 2015, news leaked that the celebrity wedding happened and that Gwyneth Paltrow and Robin Antin were there. Rocker Madden opened up for Diaz’s birthday with a sweet Instagram post calling her his “One & Only. True Love.”
Adam Brody and Leighton Meester
Adam Brody (best known for his role in "The O.C" and "Gilmore Girls" ) and Leighton Meester ("Gossip Girl" and "Single Parents") crossed paths in 2013 and married in 2014. We don’t get much information voluntarily, but Meester did share with "Shape" that she’s a surfer. Brody taught her it’s something they enjoy doing together.
In December, in full wet suits, of course, the "Single Parents" actors have photographed longboarding off the coast of Malibu. The couple has two children. Brody says that parenthood is “pretty magical.” Although they are private about their life, they do occasionally share photos on social media both of themselves and their children.
Margot Robbie and Tom Ackerley
Chances are you haven’t heard that the two-time Oscar-nominated actress Margot Robbie is married to British filmmaker Tom Ackerley. The couple has kept it very quiet. They met on the set of a 2014 film project. Robbie acted, and Ackerley assisted with directing. Margot is best known for her role in "The Wolf From Wallstreet," and Ackerley Is most recognized with "Tonya" and '"Terminal."
People were curious. Swirling rumors finally settled with an in-your-face Instagram engagement photo; she shows us the ring, and she gives us the ring finger. These days the lovebirds run LuckyChap Entertainment. What’s that? Here are a few of their titles: "Promising Young Woman," "I, Tonya," and "Birds of Prey," plus Hulu’s "Dollface."
Dave Franco and Alison Brie
Dave Franco and Alison Brie adore being married, and they love working with each other. Most recently, they dove into "The Rental" with Brie acting and Franco directing for the very first time. They also enjoyed working together on "Disaster Artist" and "The Little Hours." The two have been in the industry for years, and although they are not raving the headlines, they are considered a true promise in Hollywood.
The couple is rarely photographed in the wild, but Franco let some privacy slip in "The Rental." In an exclusive "Interview" magazine interview, Brie fields a series of questions by Franco. In the piece, the "Community" and "GLOW" actress shared that her husband wrote the script in their normal conversation voices.
Cobie Smulders and Taran Killam
Cobie Smulders is a name you’ve seen in film credits way more than in gossip magazines. The Marvel actress starred in "Avengers," plus all three sequels, as SHIELD agent Maria Hill. She’s also in "Spider-Man: Far From Home" and "Captain America: Winter Soldier."
Prior to that, you’d know her in "How I Met Your Mother." On his part, Killam’s known for his long stint with SNL. Now he’s on "Single Parents." There’s at least one media story about the couple. According to Killam, who dished the deal to "Us Weekly," they fell in love on a road trip in 2005.
Maya Rudolph and Paul Thomas Anderson
This couple has been together since around 2001, but little is known about them as they have managed to keep themselves under the radar for more than two decades. Few pictures exist. When an unflattering paparazzi image that caught them walking together came out, Anderson responded with a Tweet, “We look like we’re going to kill someone.”
Maya Rudolph, the comedian we recognize impersonating Beyoncé and Kamala on SNL, calls Paul Thomas Anderson her husband and shares four children with him, but technically, the pair are not married. Love, however, has endured. When the eight-time Oscar-nominated director was asked how often Rudolph makes him fall down laughing, he said, “Everyday.”
Javier Bardem and Penelope Cruz
For Javier Bardem, it’s all about “protecting us.” As such, we have few relationships revealed from the couple, and those that exist are mostly found in their onscreen love affairs. After ten years of marriage and having met in the early nineties, they’ve kept their private life sealed.
In a rare display of affection, in an acceptance speech at Cannes for the best actor award, Bardem gushed, “I share this joy with my friend, my companion, my love: Penélope: I owe you a lot, and I love you so much.” They are still going strong and are considered one of the more stable couples in Hollywood.
Rose Byrne and Bobby Cannavale
Rose Byrne and Bobby Cannavale have been together for a while, since 2012, to be exact. Few know much about their relationship, but people assume they are married. It’s a valid assumption; Cannavale calls Byrne his wife. At an appearance on "The Late Show," Cannavale had to face the awkward question, “Why?”
He told James Corden it’s because he hasn’t found a better word. Neither “girlfriend” nor “partner” appeal. We have, however, seen them together. In "Adult Beginners," they play a married couple, and they also share the screen in "Annie and Spy." Lately, they’ve been taking full advantage of isolation, hunkering down with the kids.
Amanda Seyfried and Thomas Sadoski
These two dashed off together and got married in 2017. It was a surprise when they announced it on late-night television, especially since they both had been committed to one another until the fall of 2015. After an intense six-month romance, the two tied the knot. Seyfried is best recognized for her role in "Mean Girls," and Sadoski is best known for his role as Don Keefer in "The Newsroom" and playing in "Life in Pieces."
Now they have two children and a beautiful life together. We get an occasional peek at it via Instagram. On their third anniversary, Seyfried and Sadoski are pictured smooching with the message, “Happy 3, Tommy.”
Taylor Swift and Joe Alwyn
Taylor Swift kept her relationship with Joe Alwyn as private as possible. However, it all leaked out after the release of her two new albums. Alwyn collaborated and even contributed music on the piano, so the two were not only romanticly involved but also spiced up one another professionally.
When she opened up with Paul McCartney in a "Rolling Stone" interview and confirmed that the relationship was something, she tried to keep private, discussing vividly the frustration of trying to ditch the paparazzi. It’s definitely something to protect. Fast forward six years, and the couple decided to go their separate ways and brought a fairytail romance to an end.
Kirsten Dunst and Jesse Plemons
Jesse Plemons broke into show biz as "Breaking Bad’s" bad boy Todd. And you probably recognize Kirsten Dunst by her upside-down kiss with "Spider-Man." Their worlds collided on the set of the FX series "Fargo" in 2015, playing a married couple. Speculation swirled and was seemingly confirmed when Dunst left her boyfriend in 2016.
Two months later, "Us" caught Plemons and Dunst kissing. In 2017, the story was out. "Us" announced the pair’s engagement. And, voila, they welcomed a baby boy the following year, in May 2018. As far as we know, they are still engaged and haven't tied the knot, but who cares.
Claire Danes and Hugh Dancy
Claire Danes and Hugh Dancy are married? Yep. "Homeland" star Claire Danes, who also played Juliette in Leonardo DiCaprio’s Romeo, has found a star-crossed love that’s all her own. Hugh Dancy, who plays the lead in "Hannibal," is her man. They have been together for more than a decade and manage to keep their love affair tucked deep under and away from the public eye.
The couple is not a big fan of social media PDAs, but they met in 2007 on the set of "Evening" and have been married since 2009. They married secretly in France, and now they have two sons.
Robert Pattinson and Suki Waterhouse
Robert Pattinson learned a few things about the relentless nature of celebrity media while dating Kristen Stewart. The "Twilight" hunk has not made a peep about his current relationship with Suki Waterhouse, and neither has she. It’s all very hush-hush, but that didn’t stop "In Touch" from publishing a new baby rumor.
Apparently, pretty much everyone knew they were trying to get pregnant, but the stunning model proved the rumors were just that. The unreliable source also says the tight-lipped couple is planning to marry eventually. The baby bump never surfaced, and "Gossip Cop" called "US" out. Who knows, maybe one day they will surprise us, and we will witness Waterhouse walking down the aisle.
Florence Pugh and Zach Braff
Presumably, Florence Pugh and Zach Braff got to know each other by making Braff’s film "In the Time It Takes to Get There." A shot of them walking hand in hand in NYC weeks later would seem to confirm the assumption. They’ve tried to keep their relationship under wraps because of what Pugh calls a “toxic vibe” seeping out of the internet.
Instagram followers attacked an image of her and former "Scrubs" star Braff together within seconds of posting because they thought a 20-year age difference was somehow bad. So, it’s no wonder the couple tries to stay private and make us mind our own business.
Phoebe Waller-Bridge and Martin McDonagh
Showrunners Phoebe Waller-Bridge and Martin McDonagh made their dating life official in 2018. Since then, Waller-Bridge was named the most powerful person on TV, and McDonagh won three Golden Globes for "Three Billboards," including Best Motion Picture. "Fleabag" and "Killing Eve" writer and actress Waller-Bridge once shared her adoration of a play by McDonagh, but, in general, the couple refuses to comment.
Like many couples in the industry, Waller-Bridge and McDonagh keep their love life to themselves and don even take the time to update their social media feeds with photos of their personal life. Maybe that's the secret to a happy marriage.
Garrett Hedlund and Emma Roberts
Garrett Hedlund and Emma Roberts roared into 2021 with their new infant son Rhodes who was born in December 2020, as shared on social media. She went on to remark on the pressures of Twitter and Instagram and the constant exposure. The couple kept the real story as lowkey as possible, and in January 2022, the two went their separate ways. But not much else about their relationship has been revealed.
Roberts opened up with a "Cosmopolitan" cover story saying, “Sometimes it makes me sad that I can’t have a private moment." The price celebs pay for being big Hollywood stars can sometimes go out of proportion, and for them to find a quiet spot without anyone recognizing and bothering them can be something only to dream about.
Michael Fassbender and Alicia Vikander
It seems this couple met at the 2013 Toronto Film Festival and then took a trial run playing husband and wife on "The Light Between Oceans." Michael Fassbender and Alicia Vikander appeared together at the premiere of the 2016 film, and they were married in 2017.
Recently, Vikander shared a sweet gift Fassbender gave her with, "Good Morning America." She said he took her on a surprise trip to see her family in Sweden, Europe. “I was able to hang out with my mom and my dad and a lot of family members I haven’t seen in a long time.”
Julia Roberts and Daniel Moder
Julia Roberts and Daniel Moder’s relationship launched in turbulent skies, with both of them in previous relationships and Roberts offering $100,000 to cameraman Moder’s ex-wife Vera for a divorce settlement. But that was years ago. They married in 2002 and have three children. Roberts has publicly said that her hubby Moder is still her “favorite human.”
Roberts has adorned our screens in many great Hollywood moments; however, she will forever be remembered for her role as Vivian in "Pretty Woman." Moder I most recognized for "Secret in Their Eyes," and together, they are one of the strongest couples in the industry.
Peter Sarsgaard and Maggie Gyllenhaal
Peter Sarsgaard from "Dead Man Walking" and "Dark Knight" star Maggie Gyllenhaal have been together since 2002. In 2009, they married in a quaint Italian chapel in the ancient city of Brindisi, located in the heel of Southern Italy. In the past few years, the pair have been collaborating on "The Lost Daughter."
Gyllenhaal directs, and Sarsgaard stars in the story based on the novel by Elena Ferrante. Gyllenhaal was nominated for a Golden Globe for her work on "The Deuce," an HBO series she produced and starred in. For now, Sarsgaard and Gyllenhaal are still strongly hooked on one another.
Brooke Shields and Chris Henchy
Brooke Shields and Chris Henchy were introduced by friends in 1999 on the Warner Bros. lot. They announced their engagement the following year. "Funny or Die" creator and long-time writing collaborator of Will Ferrell, Chris Henchy, and ‘80s supermodel turned actress Brooke Shields live in NYC with their two daughters.
The family made a rare red-carpet appearance in February of last year. They were photographed together for the release of "Impractical Jokers: The Movie." Since then, the couple are not seen together very often and managed to preserve whatever's left of their private life to themselves.
Jason Sudeikis and Olivia Wilde
Jason Sudeikis and Olivia Wilde began their under-the-radar relationship in 2011. They’re hardly ever photographed together, but they do share two children. At the start of 2021, after a nine-year relationship, the quiet couple quietly separated, effectively putting an end to their engagement. PDA photos emerged, but these showed Olivia Wilde with a new man, Harry Styles.
Sudeikis is dealing with it by diving into new acting commitments, and "US Weekly" says he is hoping and waiting for Olivia to come back to him. The separation of the two came as a big surprise to many, not only in the industry, as most people didn't even know that the two were together at the time.
Keira Knightley and James Righton
Actress Keira Knightley and keyboardist James Righton have two children together. Neither maintains a social media presence, so few PDAs exist. The actress who is known for "Pirates of the Caribbean" and "Atonement" met Righton in 2011, and they married in 2013 in the south of France. Righton sings and plays for a London electro-rock band and released a solo album in 2020.
Knightley has been honored for her humanitarian work. In 2022 she signed a contract with Apple TV+, and she produced and starred in "The Essex Serpent." Keira is known for her five-year relationship with Rupert Friend, and James has had his share of Hollywood glam with a few other women he dated in the past.
Paul Dano and Zoe Kazan
This couple is ultra-private. The last we heard from them came in the form of a new baby announcement. Having said that, it was very low-key; they didn’t even release her name at first. Actor/writer/director Paul Dano and Zoe Kazan met in 2007, putting on a play, the first collaboration of many to come.
Dano joined Jimmy Fallon on "The Tonight Show" in 2018 to announce their film "Wildlife" and to confirm the news of their baby girl. Kazan, a Yale graduate who is an actress known for "The Big Sick" and a playwright, cowrote "Wildlife." Next, she will star in the Netflix miniseries "Clickbait."
Diane Kruger and Norman Reedus
Diane Kruger and Norman Reedus ("Walking Dead") publish social media PDAs all the time. These affections, however, are reserved for their darling daughter. At the same time, they are so super-private they have refused to include photos of her face. Plus, they’ve yet to announce her name!
The couple came out as an item in 2017 and welcomed their daughter in 2018. When the paparazzi caught an image of their daughter, actress Kruger responded forcefully. Blurring out her child’s face, she reposted it asserting, “We, as parents, want nothing more than allow her to grow up in privacy and safety.”
Gwyneth Paltrow and Brad Falchuk
This pair met on "Glee." With Brad Falchuk as co-creator and Gwyneth Paltrow on as a guest star, their behind-the-scenes romance was heading toward steamy by the summer of 2014. By April 2015, it was official. Relationship details are few and far between with this couple, which seems pretty counterintuitive given Paltrow’s TMI tendencies.
However, in April of 2020, they revealed the inner workings of their household. Holding down the fort with Gwyneth’s two teens can get tense. She said. “You know, we have the added dynamic of, like, stepparent,” affecting the family. Gwyneth was mostly associated with Chris Martin, Coldplay's lead singer, and they have two children, Apple and Moses.
Taraji P. Henson and Kelvin Hayden
“I said yes y’all!!!” "Empire," Empress Taraji Henson gushed. That’s how she captioned a photo of her sparkling rock on Instagram in 2018. Ex-NFL Super Bowl and great Kelvin Hayden set the date for spring 2020. Work schedules, family plans, and logistical problems bumped the wedding date again and again. Henson wrote, “I don’t think people understand what goes into wedding planning.”
Alas, after a two-year engagement, Henson announced that plans to marry were canceled. Permanently. Henson hasn't managed to repeat the success she had in "Empire," and for Hayden, well, he has been working very hard to keep out of the limelight.
Chris Hemsworth and Elsa Pataky
Marvel legend Thor-actor Chris Hemsworth and Elsa Pataky have enjoyed a quiet marriage in their home Down Under. But the Australian couple was spotted in the wild celebrating their 10th anniversary with holiday photos of Christmas 2020 on Instagram. The pair share three children and a lot of love.
Pataky is a Spanish actress, born in Madrid, but has been living in Australia with Hemsworth since they married. Thor returned to movie theaters in 2022 with "Love & Thunder. Fans can also get their Hemsworth fix with the Netflix exclusive "Extraction." The couple has been together for more than a decade, and it does look as if they are going anywhere.
Helen Mirren and Taylor Hackford
This couple is well-acquainted with the under-the-radar Hollywood marriage lifestyle. In 2018, they celebrated 20 years together. Helen Mirren shared that she and Taylor Hackford rang in the New Year and dined at a fish restaurant in the south of Italy to honor it. Hackford’s birthday is on New Year’s Eve, as is their wedding anniversary.
The two tied the knot at a Catholic church in Scotland and have been a loving, but not romantic, couple ever since. Mirren says she’s not into Valentine’s Day or anything like that and is just happy to spend her days with an interesting conversationalist and one of her best friends.
Elliot Page and Emma Portner
Most of this couple’s open displays of affection will be found on Instagram, so it’s fitting that their romance took flight there. A flurry of exchanges of photos, videos, and comments went full circle in January of 2018, with an image of Elliot Page and Emma Portner’s nuptial bands matching and fingertips touching.
After two years of marriage, "Juno" star Page came out, and Portner took the opportunity to express her love and support. That said, the two recently called it quits after three years of marriage. Overall, they had a good relationship and, in Hollywood terms, lasted a long time, however, when a celeb dated a celeb, the odds are not in their favor.
Elle Fanning and Max Minghella
Relationship rumors between Elle Fanning and her Teen Spirit director Max Minghella have been percolating for a long time. Neither chose to address being caught cuddling in London in 2018. Most people think it’s their age difference that has kept it so quiet. But then, in 2019, the pair showed up at the MET Gala hand in hand.
Twelve years is not a big deal, and we've seen bigger stars with bigger age gaps. Minghella is best known for starring on "The Social Network" and "The Handmaid's Tail," and in recent years, he has been spreading his talent in directing and screenwriting.
Carrie Coon and Tracy Letts
Carrie Coon and Tracy Letts fell in love during the 2010 season of “Who’s Afraid of Virginia Woolf?” at the Steppenwolf Theatre Company in Chicago. Both nabbed Tony Award nominations. Letts had already received the Pulitzer in 2008 for his play August: Osage County.
They starred in "The Post" together in 2017 and welcomed a baby boy in 2018. The couple wed in 2013. Whenever Letts finishes a writing project, he relies on Coon’s feedback. He sits nervously in another room, listening, and then asks which parts made her laugh. Just as adorable, Coon is moved; he cares so much.
Amber Tamblyn and David Cross
"Arrested Development" star David Cross and actress Amber Tamblyn prefer privacy. The couple married in 2012 and share one child, a daughter. "The Sisterhood of the Traveling Pants" actress Tamblyn announced her birth in 2017. But sometimes, it’s impossible to keep things under wraps.
Tamblyn, an open feminist, faced the dicey media situation of finding her comedian husband (“rightfully”) accused of making discriminatory comments to co-star Charlyne Yi in the form of a bad joke. Tamblyn said the incident found them confronting hard times. The media storm blew over, and their life is private again.
Chelsea Peretti and Jordan Peele
Filmmaker Jordan Peele and actress/comedian Chelsea Peretti are a low-key couple, to say the very least. They married secretly in 2016 and had been dating since 2013. Their courtship, however, was very much in the open. Peele adorably proposed to Chelsea via Tweet.
No words, just an engagement ring emoji and her Twitter name. Five months later, Chelsea posted a picture of a dog and this note: “[red heart emoji] eloped a bit ago.” The only witness was the pup. Now they have a little boy as well, born in July 2017. It is clear as day that these two were natural-born storytellers.
Jeffrey Dean Morgan and Hilarie Burton
These two were together ten years before they married in 2019. Hidden away in a quaint New York state farmhouse, Jeffrey Dean Morgan and Hilarie Burton reside there with their two kids, far from the bustle of the Big Apple. "Grey’s Anatomy’s" Morgan met "One Tree Hill’s" Burton at CW, sort of.
"Supernatural" star Jensen Ackles knew both actors and decided the two should meet on a blind date. They met up on a double date with Ackles and Danneel Harris at an LA bar, drank too much, and never parted. It wasn’t just the booze, Burton told "People," “His confidence was intoxicating.”
Joshua Jackson and Jodie Turner-Smith
This couple’s whirlwind romance kicked up in 2019 and closed out the year with "US Weekly" breaking the news of their secret wedding. British model Jodie Turner-Smith and actor Joshua Jackson met at his celeb-heavy 40th birthday bash at a West Hollywood club. Showbiz media tracked every move for details.
Finally, the couple made a red-carpet appearance at AFI Fest for "Queen & Slim." After two years, Turner-Smith opened up, saying their bond only grows stronger. Meanwhile, the former "Dawson’s Creek" star called the year that also brought their baby girl into their lives “the happiest whirlwind” of his life.
Daniel Craig and Rachel Weisz
This pair is surprisingly low-key, considering they’ve been friends since 1994. British actors Daniel Craig and Rachel Weisz met long before he was 007, and she was an Oscar-winning actress. But they didn’t start seeing each other as-more-than friends until the end of 2010. It happened after starring as a married couple in "Dream House."
They secretly married a year later in a very intimate ceremony. The couple welcomed a daughter in 2018. Since then, we haven't heard much about either, not because they are not up to anything but because they are so good at keeping everything under the radar.
Lady Gaga and Michael Polansky
Lady Gaga and wealthy financier Michael Polansky have been an item since they were caught smooching at a New Year’s Eve bash heading into 2020. They’ve been together since then. Polansky accompanied her at the inaugural event in DC. Earlier in 2020, Gaga hit Instagram with a post saying they’ve been hunkering down together, playing cards and video games.
Sources say he likes to lavish on her. The Oscar-winning singer told Morning Joe he is the love of her life. They work very hard to keep their private life a secret so no one knows how happy or unhappy the couple truly is.
Ashley Olsen and Louis Eisner
It’s no wonder "Full House" twin Ashley Olsen avoids publicity like the plague. She turned to the fashion industry and left acting behind at 18. Now she has something else to protect from the spotlight—her boyfriend Louis Eisner, an artist out of Los Angeles.
Nobody knows how they hooked up, but they were first spotted in Los Angeles at Hammer Museum’s Gala in the Garden in 2017. Their bi-coastal relationship has been solid ever since. They make it work with Eisner staying with Olsen in New York and she, with him, in LA.
Liam Hemsworth and Gabriella Brooks
Let's face it - the Hemsworth brothers are never not single - it's just not in their nature. Exhibit A. These lovebirds have been dating for over a year, and it looks like things are getting serious. "Hunger Games" actor Liam Hemsworth and English model and actress Gabriella Brooks hosted a New Year’s Eve party at Hemsworth's sprawling Aussie property.
Plus, it seems she may have moved into the estate. Also, Brooks was recently on Hemsworth’s arm at a family birthday party for older brother Luke Hemsworth’s 40th. It’s been kept quiet, no doubt, since Hemsworth and Miley Cyrus were married and divorced, all within a year, ending in 2019.
Christina Aguilera and Matthew Rutler
Matthew Rutler was a production assistant on the set of "Burlesque "when he met superstar Christina Aguilera in 2009. The pop diva played a small-town girl who makes it in LA. This couple dishes bold shares on social media but not much in the way of relationship deets. To the point they announced their engagement six years ago.
It was a cryptic Instagram post that has left fans on the edge of their seats since Valentine’s Day 2014. Their daughter Summer Rain is six years old, and they’ve been together for over 10 years.
Kit Harington and Rose Leslie
Kit Harington and Rose Leslie are famous for trying to kill each other on "Game of Thrones." Memorably, Ygritte shoots three arrows at Jon Snow. It’s not your average love story. The pair’s real-life love story is more conventionally romantic. They’ve been living in their English Tudor manor house since GOT concluded.
At the end of 2020, they announced their first child was on the way, but no forthcoming details. They have been together for more than two decades and seem to be one of the strongest and most stable couples in the show biz.
Joseph Gordon-Levitt and Tasha McCauley
This furtive duo married secretly in December 2014. Before that, all we knew was that Joseph Gordon-Levitt had a girlfriend and that neither of them wanted to openly discuss it. Now it’s out. The actor/director is married to Tasha McCauley, co-founder and CEO of a robotics company based at NASA’s research park in Silicon Valley.
She met the "Third Rock From The Sun" star on a blind date organized by a mutual friend. Tasha McCauley is a very talented woman and has spread her talent in various films, however, no matter what she puts her hands on, she will always be most recognized as Levitt's better half.
Sean Penn and Leila George
Sean Penn has had an array of prominent wives. He was married to Madonna in the ‘80s and parted ways with Charlize Theron in 2015. Since then, Penn and Leila George have been linked. It came out that they were a couple in 2016, and they tied the knot in the summer of 2020.
It was a happy trajectory to an on-again, off-again relationship. Word is, they bonded during quarantine. So, it seems natural that they had a Zoom wedding. Don't get too excited, though; perhaps all that bonding time got too much, as now they're since gotten divorced
Cate Blanchett and Andrew Upton
Cate Blanchette and Andrew Upton have been married so long that they exchange gifts like microwaves or vacuum cleaners for their wedding anniversaries. The two-time Oscar-winning actress met Upton on the set of a TV show in 1996. He proposed after three weeks of dating.
The pair from Australia were joint artistic directors for the Sydney Theatre Company for five years. The "Lord of the Rings" actress says they homeschool their four children at their house in Sydney. Now we understand why their relationship is so quiet. With homeschooling four children, no wonder she doesn't have time for showing off her clan on social media.
Cheryl Burke and Matthew Lawrence
These two lovebirds met on a blind date and were together for a year. They went their separate ways but then, guess what - they reunited ten years later! "Dancing With the Stars" contestant Cheryl Burke and former "Boy Meets World" star Matthew Lawrence got back together in 2017.
After two years of romance and a charming wedding proposal on her birthday, the lovebirds celebrated their bond by tying the knot at a grand fairy tale wedding in the month of May 2019; however, by the time September 2022 came roaring in, the couple was already divorced.
Ellen DeGeneres and Portia De Rossi
Since Oprah bowed out, Ellen DeGeneres took the top spot on the podium of America’s most popular and beloved talk show hosts. With her wife, Portia De Rossi, by her side, the pair have been enjoying the spoils of their success together.
Rumors came about their divorce; however, the rumors remained rumors. The couple keeps us updated regularly on their Instagram accounts, and they are stronger together than ever. You go, girls! In February 2023, the two lovely ladies renewed their vows. They may be quiet about the juicy details of their relationship, but they are very public about their love.
Tom Selleck and Jillie Mack
At 38, single, Selleck was feeling a bit lonesome. So he saw 'Cats,' a show that he loved so much he kept going back for more. But there was a reason for his fascination with the musical – actress and dancer Jillie Mack starred in it! The pair went for dinner, and the rest is history – 32 years of history, to be exact.
She was then seen at every event Selleck was invited to – red carpets, awards shows, and ceremonies - she was “his girl.” The two tied the knot in 1987, welcoming their bundle of joy, Hannah, into the world just a year later, at which point Selleck quit 'Magnum P.I' to focus on his family.
Sacha Baron Cohen and Isla Fisher
Whether you know him as Ali G, Borat, or Bruno, Sacha Baron Cohen has to be one of the funniest (but also one of the most controversial) men in Hollywood. And by his side, an equally funny and stunning wife, Australian actress Isla Fisher. Meeting back in 2002, the pair first laid eyes on one another in Sydney.
What seemed to be love, at first sight, saw the pair walking down the aisle two years later in a Jewish ceremony in Paris. Isla converted to Judaism for her man, and now they have three children together, splitting their time between London and LA. What a life, right?
Oprah Winfrey and Stedman Graham
The ultimate inspiration for any female with a dream, it seems that Oprah Winfrey has also nailed it when it comes to her love life. The magnanimous talk-show host and multi-billionaire know a thing or two about life and relationships, and while she’s not married to her long-term partner Stedman Graham, she's still managed to keep a steady relationship for 32 years!
Graham himself is a businessman, author, and podcaster. While many men would stay away from a woman so powerful and wealthy, Graham has been in for the long haul. The pair were acquainted in 1986 and have been by each other’s sides since then.
Michelle Pfeiffer and David E. Kelley
Set up on a blind date back in 1993, Michelle Pfeiffer had no idea she’d be meeting the man she was going to marry. After 25 years of marriage, Pfeiffer claims that TV writer David E. Kelley makes her feel “like the luckiest girl in the room!” Pfeiffer says that “Life is made up of choices, and I’ve not always made good choices but I know I picked the right man.” Well, that’s quite the compliment!
Within 10 months, the pair were saying “I do,” much to people’s surprise. But people were wrong, and while they speculated it wouldn’t last, we think 25 years is enough proof, don't you?
Michael J. Fox and Tracy Pollan
Michael J. Fox rose to fame on our television screens going as far back as 1976. For you millennials, he’s the guy who plays Marty McFly in the 'Back to the Future trilogy. Anyway, we’re here to talk about love, something which Michael J. Fox and his darling wife, Tracy Pollan, have loads to give to one another.
The pair got together in the 80s, first meeting while Pollan was shooting 'Family Ties', but it wasn’t until two years later, on the set of 'Bright Lights, Big City' that they started getting more serious. Fast forward three decades, and Fox and Pollan are still together, especially through crucial years up to today, with Fox suffering from Parkinson’s disease.
Sting and Trudie Styler
From The Police to his solo act, Sting has an instantly recognizable voice that puts him down in history as one of the greats. What’s more, is his personal life: he and his wife, Trudie Styler, have been together for more than a quarter of a century! Meeting in 1982, the pair dated for ten years before finally tying the knot in 1992.
It seems that to spend 35 years with someone must mean they’re doing something right - close friends say that the couple's love is almost teenage-like, in the sense that they’re just so into each other. And Sting himself backs this up, revealing that Trudie remains light in his life (as well as their four kids together).
Gisele Bündchen and Tom Brady
Brazilian supermodel Gisele and her New England Patriots quarterback husband, Tom Brady, are incredible together. It just took a meeting to really seal the deal. In 2006, the pair met at a mutual friend’s house, and since then, they've been joined at the hip.
Super aligned with their beliefs and lifestyle, this couple was made for each other. We’re sure when Brady was a teen, he wouldn’t have dreamed of marrying a stunning Brazilian woman – but hey, life! The pair tied the knot in 2009 and haven’t looked back, welcoming a boy and a girl into their lives.
Warren Beatty and Annette Bening
With a 21-year age gap, we’re once again shown that age is just a number. Especially when that gap hasn’t stopped Annette Bening and Warren Beatty for 27 years. The pair married in 1992, just a year after she split from her former husband, Steven White.
Beatty, on the other hand, is a bit of a legend, and he’s been acting for almost 50 years. His creative talents as a filmmaker and actor wowed many women in the past, and we’re sure Bening was no exception! The pair have raised four kids together and are looking toward a bright future together.
Harrison Ford and Calista Flockhart
With his debonair charm and signature smirk, it’s no wonder Harrison Ford wooed the likes of Calista Flockhart. The pair have been married since June 2010 and really seem to be enjoying married life together. With such an unwavering relationship, the pair support each other through everything – for Harrison Ford, it’s aviation! Couples that support one another stay together.
With such an unwavering relationship, the pair support each other through everything – for Harrison Ford, it’s aviation! Couples that support one another stay together. You will never see these two on the front pages of magazines, never see them on gossip columns, as they manage to preserve a stable and true love story.
Sarah Michelle Gellar and Freddie Prinze Jr.
Buffy the Vampire Slayer meets Fred Jones, and apparently, they liked the look of each other enough to get married. Anyway, characters aside, the pair has remained married for almost twenty years. The secret? “We were just friends. That’s one of the reasons I think our relationship has always been so good,” Freddie said.
The pair met on the set of 'I Know What You Did Last Summer' and started their friendship there. So hey, friends first, lovers later! And they have been going strong ever since. They are, without a doubt, one of our favorite couples on the list.
Adam Sandler and Jackie Sandler
Hollywood funnyman Adam Sandler is pretty much a comedic genius when it comes to the genre. Anyone who disagrees, well, they clearly haven’t seen 'Happy Gilmore.' The king of late 90s comedy films, Sandler kept himself busy (and still is keeping busy). You’d think with a hectic schedule that, your love life would take a bit of a hit, but that is not the case for Sandler.
He makes sure to set aside time for his family, which we think is extremely important. Devoted to his two daughters and wife of 20 years, Jackie, Sandler is quite the family man. We’re sure that the checks he brings into the family also help with keeping that marriage strong.
Jamie Lee Curtis and Christopher Guest
The stunning Jamie Lee Curtis and her beau Christopher Guest have been married for over thirty years. We love the way they “met,” too: Curtis, in fact, spotted Christopher Guest on the cover of a magazine one day. From that one picture, she proclaimed that this man would be her future husband. And it actually happened!
The pair have two children together. And did you know that Christopher Guest has the title of a Baron? Pretty cool! Jamie Lee Curtis and Christopher Guest are Hollywood's old school, and not because of the year they were born. They have class, they have style, and they have an amazing relationship we can only envy.
John Travolta and Kelly Preston
Hitting our screens with some knee-dropping, toe-tapping, and electric dance moves, the star of 'Saturday Night Fever is a Hollywood heavyweight. But back to his love story, John Travolta came across Kelly Preston on the set of 'The Experts in 1989.
The pair married two years later and enjoyed 28-year marriage that produced three kids. Tragically in July 2020, Kelly passed away in Florida. They will always be remembered as one of Hollywood's greatest couples. They were magic between to two whenever they walked the red carpet together, and there are only a few pairs in the industry that kept on strong as these two did.
Cyndi Lauper and David Thornton
For the singer of “Girls Just Wanna Have Fun,” you kind of wouldn’t expect Cyndi Lauper to be going with one guy for most of her life, right? Well, it seems Ms. Lauper is precisely the opposite and has remained with her partner in crime David Thornton for a staggering 28 years!
Despite the fact that Hollywood is rife with lawsuits and divorce proceedings, these two prove that relationships in Tinsel Town can, in fact, survive and even thrive. When the pair met, Cyndi was at her worst, going through a bit of a rough patch with her relationships. At the time, she had been dating her manager on and off. Fast forward, Thornton and Lauper met, became friends, and, before they knew it tied the knot in 1991.
Sarah Jessica Parker and Matthew Broderick
"Sex and the City" meets "Ferris Bueller," this Tinsel town couple has been together through it all. The fashionista from Hollywood, Sarah Jessica Parker, found her man in Matthew Broderick, and they’ve lasted for just over two decades. The pair first locked eyes on one another when they were introduced through Sarah’s brother.
It seems that while they keep their personal life under wraps, Sarah Jessica did provide some insight as to her true feelings: "Call me crazy, but I love him. We're very devoted to our family and our lives. I love our life. I love that he's the father of my children, and it's because of him that there's this whole other world that I love.”
Anna Kournikova and Enrique Iglesias
We're sure Enrique has serenaded his wife of almost two decades, Anna Kournikova, many, many times! The couple started dating after meeting in 2001 on the set of his “Escape” video clip. At 21, Kournikova gave up the Wimbledon pursuit and decided to follow her heart instead. Fast forward, and Enrique and Anna have a gorgeous set of twins together, who seem to love their football as much as their dad.
Not to mention inheriting the good looks from both sides. They are one of the modest couples in Hollywood and maintain a quiet and stable relationship. Even though they have been together for so many years, the two never officially married.
Catherine Zeta-Jones and Michael Douglas
The stunning Catherine Zeta-Jones shocked the world when she and Michael Douglas announced their engagement. The Welsh beauty has taken the leading lady role in many films, from "Entrapment" to "The Mask of Zorro." And Michael Douglas, well, his reputation precedes him – we really don’t have to list his slew of films!
Prominent in Hollywood, the pair have grown from strength to strength and stuck by one another. Despite signing a prenup before saying “I do,” it’s highly unlikely that the pair will need to call in the lawyers, a la "Intolerable Cruelty!" Almost twenty years later, the pair have two kids together and have earned a lavish lifestyle. Cheers to that!
Goldie Hawn and Kurt Russell
These two screen veterans are still together after more than 35 years. You might remember the hilarious rom-com 'Overboard', which saw a snobbish Hamptons-loving socialite suffer from amnesia before being tricked into thinking she was married to the single father of three, played by Kurt Russell.
By that time, the pair had been dating for 5 years, deciding in 1982 that they would never marry and just raise their blended family as “committed partners.” And they’ve been committed partners ever since. Goldie Hawn once told the media that the secret to their partnership was the fact that they’d never walked down the aisle.
Nnamdi Asomugha & Kerry Washington
Nnamdi Asomugha had his breakout performance in 2017 at the Sundance Film Festival for his lead role in Crown Heights. Before that, he was one of the best cornerbacks the NFL has ever seen. His wife, Kerry Washington’s successful career on stage, in film, and on TV has spanned over two decades.
She is admired for playing Olivia Pope on the popular ABC TV series "Scandal," which earned her a Golden Globe Award for Best Actress. The couple met when Washington performed on Broadway, and Asomugha attended. She informed him she didn’t date athletes, and he responded that he didn’t date actresses. The couple married in 2013, and they have two children.
Emily Ratajkowski & Sebastian Bear-McClard
We don't have exact dates for when this couple, made up of supermodel Emily and actor Sebastian, actually started dating – or even when they got engaged. However, while the dating relationship itself might not have been very long, Ratajkowski apparently kept Sebastian in the friend zone for two years. Or, as she put it, she spent two years vetting him.
The couple tied the knot in a surprise ceremony at New York's City Hall in February 2018. The couple had maintained a quiet and modest love story and managed to keep all of the gossip to themselves. However, Rata and Seb went their separate ways in 2022.
Meryl Streep and Don Gummer
The way these two met was in the light of some dark circumstances. Streep was mourning the loss of her boyfriend at the time, John Cazale, who passed away too early in life. At the time, her brother Harry came along with a friend - Don. Just six months later, the pair said: “I do.”
Their wedding was a pretty low-key affair, happening in 1978. While he isn’t a “celebrity” in the same way Meryl Streep is, he’s quite a celebrated sculptor! He has been doing him, winning awards, and having his work featured in public commissioned art! Pretty cool!
Karlie Kloss and Josh Kushner
The supermodel, who is known for her extremely long legs and overall runway presence, did not opt for a fellow model as her spouse or even an A-lister at that. But while he doesn’t have Hollywood fame or model status, he is a very successful venture capitalist. Well, real estate heir. Lucky…both of them!
Looks, dollars, and love - seems that the model and Project Runway judge hit the jackpot! For those interested, Kushner is Ivanka Trump’s husband’s brother! Guess big wealth runs in the family… And the couple had their first child in March of 2021. As of May 2023, Kloss was pregnant with her second child.
Jerry and Jessica Seinfeld
Jerry and Jessica's love story began during their bagels and lox days, where they first fell head over heels for each other. However, their journey has evolved as they both embraced a health-conscious lifestyle. Despite their dietary changes, Jessica's Long Island Chicken Parmesan, famously cooked on their very first date, still holds a special place in their hearts.
Now happily married for almost two decades, Jerry affectionately refers to Jessica as his "best friend." Their enduring bond and mutual admiration serve as a testament to the secret of their relationship's longevity: genuinely liking and cherishing one's significant other. Clearly, affection and friendship (and a lot of jokes) can sustain love for a lifetime.
Lisa Bonet and Jason Momoa
Jason Momoa has been deeply in love with Lisa ever since he laid eyes on her in The Cosby show. The couple were together for almost two decades despite their 12-year age gap. Sadly the couple has decided to call it quits in early 2022, Lisa was also previously married to Lenny Kravitz and had one child Zoe Kravitz.
Jason Momoa is best recognized with "Aquaman," "Justice League," and many other Marvel creations, and Bonet will probably never be able to completely get rid of Denise Huxtable. She is here to stay. She played Denis for more than six years and then carried on with her on "A Different World."
Alexis Bledel and Vincent Kartheiser
The Gilmore Girls and Handmaid’s Tale star met fellow actor and husband Vincent Kartheiser when she played his mistress in the ’50s set drama Mad Men. The stars started dating when they wrapped filming, got married in 2014, and welcomed their son into the world the following year.
Since the "Mad Man" days, Bledel has continued to act in television and film, including her role as Emily Malek in the Hulu series "The Handmaid's Tale." Kartheiser has also continued to act in both television and film, including his role as the character Eddie in the Amazon Prime Video series "Das Boot."
Amy Schumer and Chris Fischer
Ever date someone who can't cook? Well, this wasn’t the case for Amy Schumer and her hubby! Chris Fischer is a chef! If we heard that, we’d be getting down on one knee too! Delicious. Anyway, the farmer who hails from the gorgeously scenic Martha’s Vineyard married the comedian and actress in 2018.
How did they meet? Fischer cooked his way to her heart when she was at his family’s farm visiting the area. The two lead a relatively modest and private life, making it sometimes impossible to recognize them walking down the road. Schumer has continued to work in comedy and acting since her marriage, with notable projects including her comedy special "Growing" and her role in the film "I Feel Pretty."
Jim Parsons and Todd Spiewak
It was 15 years before "The Big Bang Theory" actor Jim Parsons and his now-husband Todd Spiewak got together. According to Parsons, he didn’t think much of the wedding thing but decided to go ahead with it to “legalize this thing.” The two wed in May 2017 in New York City’s Rainbow Room. Prior to the wedding, Parsons never felt the need to get married, as he was fine staying as they are.
He likened the experience of being together with Spiewak as ‘close to being with God.’ Since their marriage, Parsons has continued to act in television and film, including his role as Michael in the film "The Boys in the Band."
Matt Bomer & Simon Halls
Everyone has heard of secret weddings. But not many may know that secret marriages actually exist. That is exactly what happened to Matt Bomer and Simon Halls. The two were secretly married for three whole years. Not many people knew of their marriage, and their wedding was attended only by both parties’ close family members and friends.
Bomer has continued to act in television and film since his marriage, with notable projects including his role as Larry Trainor, Negative Man, in the television series "Doom Patrol." Halls has continued to work as a publicist and has represented a number of high-profile clients throughout his career.
Jennifer Lawrence & Cooke Maroney
Lawrence managed to bag gallery director Cooke Maroney after only a few months of dating. The silver screen star started dating the director of New York's Gladstone Gallery back in June of 2018, and it wasn't long before Cooke popped the question.
They kept their relationship relatively quiet and private. The two got married in 2019 in a comparatively intimate wedding (a mere 150 guests) and are still together. In fact, the relationship has become so important to Lawrence that she's decided to take a step back from acting in order to help it stay strong.
Natalie Portman and Benjamin Millepied
The very lovely Natalie Portman, who has now relocated to Australia, is clearly a fan of keeping a relatively low profile. Do you even know who her husband is? Yeah. So the guy is Benjamin Millepied, whom she met on the set of the terrific “Black Swan” back in 2009.
He worked as the choreographer and also had a role in the film! The pair had a son first in June before Portman married him in August 2012. Since their marriage, Portman has continued to act in film, as well as direct and produce. She has also been involved in a number of philanthropic efforts, including advocating for animal rights and environmental conservation.
Alexa Demie and Christian Berishaj
Even though she’d been acting for years, it wasn’t until her iconic role as Maddy Perez in the hit HBO series “Euphoria” that gorgeous actress Alexa Demie rose to stardom. Fortunately, her real-life romance isn’t at all like the one on the show. Demie has been dating singer, record producer, and music engineer Christian Berishaj since 2017.
They met after Alexa starred in one of his music videos in early 2017, and they’ve been together ever since. Even though Alexa is extremely private about her social media posts, paparazzi have managed to sneak some photos of the couple being romantic on several occasions.
Sydney Sweeney and Jonathan Davino
The stunning blonde actress Sydney Sweeney started making waves in “The Handmaid’s Tale” series on Hulu, and then skyrocketed to fame with her role in “Euphoria” and “White Lotus.” But it seems this beauty likes to keep her private life very private, and as she’s said in several interviews – “doesn’t like to date anybody in the spotlight.”
Back in 2018, she attended an Emmy party and some other gala events with Chicago businessman Jonathan Davino. The two were later spotted at a basketball game being very cute together, and in 2022, news finally broke out that they had gotten engaged! We’re all waiting for a glamorous wedding, which we probably won’t get to see any of, seeing as Sweeney and her beau love her privacy.
Dolly Parton and Carl Thomas Dean
Even though the beloved ‘Queen of Country’ Dolly Parton has been married to Carl Dean for over 50 years, the couple has never been one to publicize their relationship. They met in Nashville in 1964, the day that Dolly arrived at the city and went into a laundromat to wash some dirty clothes. They immediately clicked and started dating, getting married two years later.
Dolly has often said that one of the reasons their relationship has lasted is because they’ve kept it private and away from all the media. She says Dean has nothing to do with show business and is a simple, loving man that balances her crazy life of fame. Well, something must be working out if they’ve stayed together for over five decades.
Lizzo and Myke Wright
The international star and singer of “Truth Hurts,” Lizzo is known for being a strong, independent woman that lives her life on her own terms. But that doesn’t mean she can’t fall in love, and she has! Since 2021, she and stand-up comedian Myke Wright have been spotted around Los Angeles and attending several parties together.
They always look very happy and laughing hysterically, which is basically what you want from a relationship. The couple have been together since 2021 and seem to be going strong. Ironically, they met in 2016, when they were co-hosting the MTV series “Wonderland.” Let’s see if there are wedding bells in these lovebirds’ future!
Gerard Butler and Morgan Brown
The Scottish actor that made his fame with “300,” “Law-Abiding Citizen,” and other dozens of hit blockbusters has quite a history of dating. But apparently, he’s been sort of steady with interior designer and real-estate developer Morgan Brown for the last nine years. Even though they’ve reportedly broken up and gotten back together many times, they seem to keep working at it.
Brown, who was also a former model, has been seen by the Hollywood actor’s side in many A-list events and film sets. Even though Brown has a child from a previous relationship, she’s revealed in interviews that she’d like to start a family with Butler. Let’s hope their insane working schedules allow it.
Naomi Watts and Billy Crudup
The “King Kong” star Naomi Watts and heartthrob from “Almost Famous” Billy Crudup have been dating since 2017, and they’ve kept it very quiet until 2022. The talented actors met for the first time back in 2009, in a Broadway play they both starred in; however, at the time, they were both involved with other people.
In 2017, they worked together in the Netflix series “Gypsy,” and sparks flew. They waited a whole five years to finally announce their relationship to the world at the 2022 SAG Awards. Since then, they’ve appeared on several red-carpet events together, with Naomi recently posting on social media for Crudup’s birthday, with the caption “Happy Birthday, my love.”
Ilana Glazer and David Rooklin
Ilana Glazer has been on the comedy scene for years, doing stand-up, producing, writing and directing her own projects. In 2014, she rose to fame when Comedy Central bought her web series “Broad City,” which she created with Abbi Jacobson. Glazer has never been to keen to reveal details on her personal life; in fact, few people knew that by 2023, she’d been married to scientist David Rooklin for over a decade!
The comedian and the scientist met in 2011 in Washington Square Park in New York City, and she describes it as love at first sight. They got married in a private ceremony in 2012 and honeymooned in Iceland. Eleven years later, they’re still very happily married.
Georges LeBar and RuPaul
The iconic creator of “RuPaul’s Drag Race” is not only a drag queen icon across the world, RuPaul is also an incredibly talented TV personality, producer, writer, host, and model. And he’s also quite private about his personal life! It turns out that RuPaul has been in a serious relationship with Australian author and rancher Georges LeBar since 1994, finally getting married in 2017.
The couple have been together for over two decades, and according to RuPaul, they couldn’t be happier. Even though their lives are completely different – one is plowing fields and writing books while the other is hosting a world-famous drag queen TV show – they’re crazy about each other.
Carrie Underwood and Mike Fisher
“American Idol” winner Carrie Underwood has seen nothing but success in the music industry since 2005. She’s also somehow managed to keep her fairytale marriage very under wraps. The beautiful blonde singer met Canadian hockey player Mike Fisher back in 2008 at a mutual friend’s party. They fell madly in love, and two years later, they got married in 2010.
In 2015, they had their first child together, a son named Isaiah; and four years later, in 2019, they welcomed their second baby boy. Carrie says she wants a large family, so it’s safe to expect more children from this beautiful couple in the very near future.
Kristen Stewart and Dylan Meyer
The “Twilight” star Kristen Stewart met the beautiful actress and writer Dylan Meyer back in 2013, but it wasn’t until 7 years later they reconnected through a mutual friend and fell hard for each other. Meyer comes from a family of screenwriters and is very much in the Hollywood scene. But undeniably, she became a household name when she started a serious relationship with Stewart in 2019.
In 2021, Meyer proposed to Stewart, and these beautiful women got officially engaged. But they certainly managed to keep the whole relationship quite private for years. It wasn’t until the 2022 Oscars party that they publicly announced they were married. Since then, they’ve been known to post the occasional romantic social media post.
Kaley Cuoco and Tom Pelphrey
Kaley Cuoco rose to fame after playing Penny in the hit series “The Big Bang Theory” and most recently in HBO’s “The Flight Attendant.” But despite seeing this blonde actress on every billboard in town, she’s been quite private about her love life, which seems to be going amazingly well. Back in April 2022, Cuoco’s agent told her she had found “the perfect match” for her, and it was “Ozark” actor Tom Pelphrey.
Remember Laura Linney’s problematic brother on the show, Ben Davis? Well, that would be Pelphrey. It seems Cuoco’s agent was right because the two actors met at an “Ozark” premiere party and fell almost instantly for each other. They’ve been dating ever since and they recently announced they’re having a baby together!
Zöe Kravitz and Channing Tatum
The “Magic Mike” star Channing Tatum and new ‘Catwoman’ Zoe Kravitz began to be the center of the Hollywood rumor mill in early 2021. They worked together in 2017, both voicing characters in “The Lego Batman Movie,” and they became good friends. Fast forward to 2019, and Tatum was divorcing Jenna Dewan, at the same time that Kravitz was splitting up from husband Karl Glusman.
Tatum and Kravitz were photographed together around NYC several times since the start of 2021, but Kravitz said they were simply collaborating together as she wanted to cast him in her upcoming film “Pussy Island.” They haven’t officially announced their relationship, but the two actors seem to be quite involved with each other.
Julie Yaeger and Paul Rudd
Paul Rudd is one of those comedy actors that’s been around since the 90s and is still one of the most beloved celebrities in Hollywood. Apart from being a great actor, he just looks like a genuinely nice guy. And his wife of 20 years, Julie Yaeger, must think so too. If you’re surprised to learn Rudd has been married for two decades, you’re not alone.
The actor and his wife keep their relationship very far away from the media. Yaeger, a screenwriter, and producer, met Rudd at his publicist’s office in the early 2000s, and they immediately hit it off. They tied the knot in a small, intimate ceremony in 2003 and have been happily married ever since. They have two gorgeous kids.
Hunter Schafer and Dominic Fike
Since her debut as Jules in the hit HBO series “Euphoria,” nobody can stop talking about Hunter Schafer. Her beauty, talent, and fashion sense are simply impeccable, and apparently, so is her love of privacy. Even though you see her on the cover of every magazine and Hollywood party lately, how much do we really know about Hunter’s personal life?
Until recently, nobody even knew she was in a relationship with “Euphoria” co-star Dominic Fike. They met in 2021 on the set of “Euphoria,” and just as their on-screen characters developed a romance, it happened in real life. By January 2022, they’d started to give hints about their relationship, and in February of the same year, they posted their first post as a couple on social media.
Lorde and Justin Warren
One thing that Lorde has always been vocal about is her need to keep her personal life private – “I’m not good at having a public-facing existence.” Well, she’s certainly managed to do so since very few people knew she’d been dating music exec Justin Warren since 2015.
Warren is the American promotions director for Universal Music in New Zealand, and he first met Lorde while working together in 2009. Six years later, they began going out and seem to still be together to this day. Even though Warren is 17 years Lorde’s senior, that doesn’t seem to be a problem at all, and the couple looks quite happy in the few photos that paparazzi have managed to sneak by.
Adele and Rich Paul
It was only in the NBA finals of the summer of 2021 that Adele and Rich Paul were seen publicly as a couple. Adele confirmed they’d only been dating for a few months, and things were going very well. Paul, who represents some of the biggest names in basketball, is crazy about the international pop star, whom he met at a party.
Adele has often said in interviews that she thinks “he’s the funniest man alive,” and what more could you ask from a partner? The two seem to be making things more official, as they were recently photographed attending the 2023 Grammy Awards together. Also, Adele has said a thing or two about wanting a second kid – with Paul!
Lisa Kudrow and Michael Stern
It’s hard to imagine the quirky Phoebe Buffay from “Friends” would keep anything private, but that’s exactly how Lisa Kudrow is about her privacy in real life. The talented actress has been married to advertising executive Michel Stern since 1995! And surprisingly, very few people knew about this.
They met in the 1980s in France, and apparently, the sparks flew almost instantly. They dated for a few years before tying the knot, though. In 1998 they had a son together, and more than 30 years later, the couple is still going strong. Kudrow often jokes about the fact that Stern is her biggest fan, that he loves watching “Friends” reruns over and over.
Ed Sheeran and Cherry Seaborn
The famous “Shape of You” singer Ed Sheeran has a love story that dates back to primary school. He and his wife, Cherry Seaborn, have known each other since they were eleven years old and studied at the same school in England. However, they were good friends for many years, only getting romantically involved in 2015 after reconnecting at a mutual friend’s party in NYC.
Seaborn had moved to the city to work in an accounting firm after graduating from Business school in England. She was also a star field hockey player in college. In 2018, the couple got married in a very small and private ceremony, which they celebrated by eating curry takeout at home.
Guy Fieri and Lori Brisson
The “Food Network” star Guy Fieri has been taking us by storm since his debut on the famous TV channel in 2006. He has his own talk shows, owns several restaurants, has authored dozens of cookbooks, and is basically the Superman of the culinary world.
He’s also a very private person when it comes to his personal affairs, such as his marriage of over 20 years to Lori Brisson. The two met in 1992 at a restaurant in California, and Fieri said he was immediately smitten by her blue eyes and blonde hair. Three years later, they got married and are still going strong two kids and 20 years later.
Maya Hawke and Spencer Barnett
Even though she’d been on screen before, it wasn’t until her role as Robin Buckley in the hit Netflix series “Stranger Things” that Maya Hawke skyrocketed to fame. Of course, it doesn’t hurt that she’s Uma Thurman and Ethan Hawke’s daughter. Apart from serious acting skills, Maya is also an amazing singer-songwriter and model and a fan of keeping her personal life out of the spotlight.
She began dating musician Spencer Barnett, whom she met at a mutual friend’s house, in early 2022. However, it was virtually impossible to find a photo of the two together. It wasn’t until August of 2022 that Barnett posted a romantic photo of them on Instagram, and it seems the young couple is still going strong.