Some might say that Leonardo DiCaprio’s most notable achievement as of late is his recent Oscar win for ‘Best Actor in a Drama’ for his performance in The Revenant. But has anyone taken the time to count the number of Victoria’s Secret Models Leo has taken to bed? Because we have. And he definitely takes home the cake on that one. Of course, that shouldn’t be too surprising given that he is rarely seen without a leggy model attached to his arm.
13. Gisele Bundchen
Leo dated Brazilian supermodel (one of the most successful of all time) on and off for five years until they called it quits in 2005. Apparently, Gisele ended it because Leo refused to settle down. Even more than 10 years later, it appears that Leo never would have changed. Another report suggested that the pair broke up at another point in their relationship because Gisele grew tired of his wild ways. Nevertheless, the two managed to still make People’s yearly ‘Most Beautiful Couples List’ during their time together, which just might be the relationship’s greatest accomplishment. She is now married to Tom Brady.
12. Bijou Phillips
Leo dated Bijou Phillips, the daughter of the musician John Phillips of The Mamas & the Papas. She is an American model-turned-actress, the two met while partying together believe it or not. The time of their relationship couldn’t be confirmed, but it happened during the late 90s. It was, as you probably guessed, relatively short-lived. Nevertheless, it was significant enough to have at least been noted on Wikipedia (so it must be significant, right?). Bijou credits DiCaprio with landing her a role in the film, Black and White. She has also appeared in Almost Famous. Bijou is currently married to That ‘70s Show’s Danny Masterson (Steven Hyde). They also have a child together.
11. Anne Vyalitsyna
During his six-month break from Bar in 2009, Leo filled in his timeline with Anne Vyalitsyna, a Russian Victoria’s Secret model, who is also best known for her appearances in Sports Illustrated. The couple vacationed together, as Leo likes do with his women, in Ibiza. Their relationship reportedly lasted a month. Anne also dated Maroon 5’s Adam Levine, which apparently was a better fit as the relationship lasted two years. Vyalitsyna and Levine posed nude on the cover of Vogue together and had an amicable split. Upon hearing of Levine’s engagement, Vyalitsyna had this to say: “I will love him forever.”
10. Bar Refaeli
Leo’s relationship with Israeli model and television host, Bar Refaeli, who was voted number one on Maxim’s Hot 100 list in 2012, this was also one of his longest relationships, clocking in at five years. The relationship, however, was one of those on-again-off-again arrangements. They started dating in 2005 before finally ending things in 2009. In that time, they stopped dating for 6 months, but they rekindled for a year beginning in early 2010. They reportedly broke up because neither one wanted to settle down. The split was reportedly amicable. Refaeli would later go to get married to another man and is expecting a child some time this year.
9. Erin Heatherton
Leo dated Erin Heatherton, an American fashion model, from December 2011 to October 2012, only a few months after he broke up with Blake Lively. She is most recognized for her work with Victoria’s Secret and, naturally, is a former Victoria’s Secret angel. She was 22 at the start of the couple’s relationship, meaning they had a pretty large age difference at around 15 years or so. The couple reportedly split because of their “busy schedules.” At the time of their breakup, it was reported that there wasn’t any animosity between the two and that they still loved and cared for one another. Heatherton eventually went on to call Leo a “wonderful person and a friend of mine” although she is in another relationship now.
8. Demi Moore
Apparently Demi Moore was a brief lover back in 1997. Rumour has it that Leo spent the night with Demi when her then-marriage to Bruce Willis was breaking down. Fast forward 15 or so years, to 2012, when Demi’s relationship with Ashton Kutcher fizzled out. Demi (reportedly) tried to rekindle her relationship with Leo by e-mailing and calling him, but he didn’t want anything to do with it according to rumors. Ouch.
Naturally, Leo has been linked to a number of women over the years. When he became linked to Rihanna last year, it was certainly a surprise to many as it seemed that Leo was straying from his usual type. However, she does fall within Leo’s age preferences with a 14 year age gap. In 2015, pictures reportedly surfaced of the two locking lips at the Playboy Mansion. Photos then surfaced again in early 2016 of them getting cozy in a private party at a Paris nightclub. Nevertheless, this relationship has never been confirmed by either party.
6. Kristen Zang
One of Leo’s first (public, at least) relationships was with Kristen Zang, a model, who he dated for 15 months in the late 90’s. She is not the most well-known celeb given that she doesn’t even have a Wikipedia page. He would have been a young 22 when they started dating — this was before he became a superstar for his role as Jack in Titanic. Before the relationship fizzled out, she was lucky enough to attend the premiere of Romeo and Juliet. She was also engaged to Nicolas Cage at one point. Perhaps she should be credited with giving Leo a thing for models?
5. Helena Christensen
Another Victoria’s Secret model for you, Leo? Well, certainly. The exception, however, is that she is of the Danish variety. The two were said to have dated briefly (a few months) in 1997, just around the time Titanic was making waves (no pun intended). However, while neither of them confirmed the relationship, it isn’t much of a stretch of the imagination. Apparently Leo wasn’t into cougars in the end (she was only older by six years, but anyone over the age of 25 is already a cougar to Leo). Their relationship wasn’t that significant to Helena, when discussing her past relationships Christensen made no mention of Leo.
4. Toni Garrn
Leo dated Toni Garrn, a German model, for more than a year (from May 2013 to December 2014) before breaking things off. It appears that Mr. DiCaprio prefers his women a little young because she was born in 1992, making her 21 years old when they started dating while Leo would have been at the ripe age of 39 or 40 – almost a twenty year age difference. They were spotted on multiple luxury yachts during their time together, although they never made it to a red carpet. Their split came after a rumor manifested that Leo came out of a hotel with 20 women. Kind of believable…
3. Naomi Campbell
The two had a little fling all the way back in the mid to late 90s, when Naomi was already a world-renowned supermodel. However, the two decided that they would be better off friends. Her personal life has been widely covered in the media, including her relationship with Robert De Niro, who she said was her “first and true love.” It was rumored that she wanted him to be the father of her children. Or did she mean the Godfather? Taxi Driver? Dirty Grandpa? Maybe they could have had The Big Wedding and had Little Fockers together after all. Wait. What Just Happened?
2. Blake Lively
Leo dated Blake Lively, the American actress known for her role in 2011’s Green Lantern. The two dated for a total of five months – from May to October 2011. They enjoyed a lot of glamorous trips around the world and were seen getting close in both Italy and France. Blake apparently also did a lot of home cooking for Leo, which impressed him. Apparently, their break-up was a shock to Leo’s family and friends who thought that Blake was “the one” for him. A source told OK Magazine that “[I have] never seen him like this with a girl.” Nevertheless, their break up reportedly came down to “distance and timing.” Blake eventually went on to marry Deadpool’s Ryan Reynolds, the two have a daughter together named James.
Kelly Rohrbach was Leo’s most recent relationship. She is a Sports Illustrated model and actress who began dating Leo in the summer of 2015 before he broke things off at the end of the year. Their relationship was relatively short-lived, lasting around six months. There was a 15 year age difference between the two. During their relationship, the couple was caught engaging in a little PDA while out riding bicycles together. They even managed to spark engagement rumors after only four months of dating. Leo claimed that she was “incredibly smart”, which played a huge role in their connection. Nevertheless, their breakup was both amicable and mutual having something to do with their busy work schedules. The two remain friends today.
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