Kidada Jones was seen in the late ’90s walking in shorts with her potential boyfriend, Leonardo DiCaprio. The two allegedly began dating shortly after her engagement with rapper Tupac Shakur ended due to the tragic fact that he had been gunned down and passed away. It’s possible that she was just using DiCaprio as her rebound guy in order to deal with the loss of her fiance, or maybe she actually hoped that the young actor and her would begin their own true love story. Either way, eventually, the two stopped appearing together, and DiCaprio soon began his serious relationship with Gisele Bundchen.
Jones is an actress, model, and fashion designer. Unfortunately, she has not been married or engaged since her 1996 engagement to Tupac Shakur, except for a short three-year marriage to Jeffrey Nash from 2003 until 2006. It’s hard to settle after dating a guy like DiCaprio, so we can definitely understand her plight. By the way, she also dated rapper LL Cool J, also known as Sam Hanna, from the popular crime show NCIS: Los Angeles.
Bijou Phillips
DiCaprio has dated some of the most highly acclaimed actresses and models of the time, but he also had a very varied taste when it came to the looks of his partners. Bijou Phillips is one of his most unique dates and has a career as an actress, model, and singer. She's currently married to Daniel Peter Masterson, an American actor who you might recall from That '70s Show, but dated none other than Leonardo DiCaprio many, many years before that.
Bijou Phillips’ acting career got a great start thanks to the young actor, who helped connect her with James Boback, the director of Black and White, a film that launched the young model's career. You can see in the picture just how different she was from the typical DiCaprio Girl, which might be the reason why they only lasted as a couple for a very short amount of time.
Trishelle Cannatella
Let's face it; if there's one type of lady that you know DiCaprio is interested in, it's artistic, young, tall blonde women with beautiful faces and perfect bodies. That might be a tall order for most guys, but when you're an A-list celebrity with one of the most recognized faces in the world, it's basically your average lady. Trishelle Cannatella, one of the actor's earlier dates, became known primarily for her appearance in the reality show "The Real World: Las Vegas," where a group of diverse strangers tries to live together in Vegas.
The actress, poker player, and Playboy model disappeared from the media's attention shortly after and has not been acting in many years. She dated DiCaprio during the height of her fame when she appeared on reality shows such as "The Surreal Life," "Kill Reality," "Punk'd," and "Fear Factor." The two eventually broke up, and we're happy to say that Trishelle Cannatella then married John Hensz.
Eva Herzigova
Another short fling for Leonardo Dicaprio happened in the late '90s when he was introduced to the Czech-Italian supermodel and actress Eva Herzigová at the film premiere of The Man in the Iron Mask, an underrated action drama with Dicaprio who stars in a dual role. Their fling was a short one, something that has become expected when you see DiCaprio starting up a romance with someone. It’s unclear whether Leo is the one who usually breaks up with these models and actresses or if he’s just not marriage material. We have a hunch that it’s probably the former.
Herzigová was born in the Czech Republic and began her modeling career at age sixteen after winning a beauty contest in Prague. She was married to Tico Torres, Bon Jovi's drummer, from 1996 until a year before meeting DiCaprio. She has since gone on to have three sons and still appears in various fashion projects. The model was pictured with young Dicaprio in some pretty intimate moments when the two were together.
Bar Refaeli
One of the most public relationships that Leonardo DiCaprio had ever had was with the beautiful Israeli model Bar Refaeli. The two met at a Sports Illustrated party in Las Vegas just shortly after Dicaprio and Gisele Bundchen had broken up their (relatively) long relationship. Perhaps he was somewhat saddened by the relationship's ending and was looking for another beautiful blue-eyed model to replace his previous love with. The two dated on and off from 2005 up to 2011 before officially breaking up their relationship.
Bar Refaeli is perhaps one of the most popular people to ever come from Israel. She is the most internationally successful model to ever come out of the small country and co-hosted the media frenzy that was the 2019 Eurovision which took place in Tel Aviv, Israel. She has two children and is currently married to Adi Ezra, an Israeli billionaire who made his fortune as a businessman. Despite the relationship between DiCaprio and Refaeli being a bit rocky, it was still one of the most popular pieces of news in Israeli tabloids at the time.