Leonardo DiCaprio dated a whole lot of models in his few decades of acting. One example of a popular model (and actress) that he used to date is the beautiful Canadian blonde Natasha Henstridge. Although appearing in various films, Henstridge never really made her impact as an actress, as her skills seem to have centered around the modeling industry. She was married to Damian Chapa, an American actor, and also Darius Campbell-Danesh, a Scottish singer and ambassador for The Prince’s Trust.
Somewhere between her two husbands, Natasha Henstridge was introduced to DiCaprio, who was on his way to massive stardom after the recent release of James Cameron’s Titanic. The two began dating, and tabloids went nuts over them, although they never publicly talked about their romance, which left the media and fans with mostly speculations. We can see how the two would have made a stunning couple with their matching baby-blue eyes.
Claire Danes
Most of you might know Claire Danes as Yvaine, the fallen star from the film Stardust. She's a three-time Emmy Awards winner and has also won four Golden Globe Awards, and two Screen Actors Guild Awards. Sure, today she is married with two kids to English actor Hugh Dancy, but back in the day — she had a great thing going with the young Leonardo DiCaprio. The actress was still just a teenager at the time they were dating, and rumors began to pile up while the two were on set together. There was a lot of controversy around the fact that Leo, who was 22 at the time, was dating Claire, as she was just 16. The two met while filming "Romeo + Juliet," and although Danes denies that the two were romantic, there is a lot of evidence to the contrary.
The two can be seen here at a red carpet event for "Romeo + Juliet," back when the young Leo still sported his classic boyish hairdo and back when jacket collars were still fashionable. Danes was also quite the looker and sported the then-popular fan hairstyle, which was all the rage at the time.
Naomi Campbell
Naomi Campbell is one of the most prolific models in the world, after establishing herself at just fifteen years old as a leader in the modeling industry. She was one of the six models of her generation declared a "supermodel" by the industry and the press. Her recent partner was an international businessman, real estate investor, and art collector Vladislav Doronin who's known today as a billionaire and for dating the iconic model.
It's been rumored that Campbell and DiCaprio were in a fling at the time, which seems to be true based on what the many photos of the two suggest. Despite having some romantic involvement together, Campbell and DiCaprio never actually dated seriously. We have no idea how anyone can resist dating a supermodel on the level of Naomi Campbell, but we’ll give the young actor the benefit of the doubt and chalk it up to teenage foolishness.
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.