The Beautiful Women of Leonardo DiCaprio

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Young Leo and His Beautiful Bridgette Hall

How would you like to be one of the ladies that have dated Leo? Can you imagine? He's such a hunk! What is better than watching Leonardo DiCaprio progress as an actor from such a young kid to now...Watching his dating history unfold as he became one of America's favorite actors who nailed many models before nailing an Oscar. Check out his dating history from regular normal girls to models! 

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Bridgette was Leo's very first model girlfriend. Man did she set the pace for the next two decades! Bridgette stated nothing happened between her and Leo, however rumor had it that Leo wasn't that great in the sack. Out the door he went.

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A Film Relationship with Brittany Daniel

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Brittany Daniel didn't get long with Leonardo back in 1994. She was able to seduce the young buck for brief moment before he started his career in dating models. There wasn't much to this relationship and no known break up to confirm.

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Leo & Kristen Zang Childhood Sweethearts Before Super-Stardom

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Leonardo and Kristen barely dated for a year and a half. This picture shows them at the red carpet for the premier of Romeo & Juliet. Rumor had it that Zang and DiCaprio split because she didn't want to be in the light of the fame from The Titanic. They ended up choosing to remain good friends.

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Naomi, Naomi, Naomi and Leo Hit It Off at One Point (or two!)

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Who would've thought that Leonardo would hit it off with Naomi Campbell? Seems to be they ran with the same group and often hooked up at different gatherings. Although Naomi was the first model Leo had dated, they quickly realized they were meant to be friends, not lovers. Although Naomi is beautiful, Leo went on to date some real hotties.

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Giselle, The One That Got Away?

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Leo and Giselle Bundchen dated for a mere five years before Giselle called it quits. Rumor has it that she was tired of waiting for him to pop the question. Although, she informed other reporters that she was in no way, shape or form ready to be engaged. Since then, these two have clearly succeeded in life considering Giselle is hotter than ever and Leo finally got that Oscar.

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Natasha Henstridge -- Model Before DiCaprio and Actress Long After

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Natasha and Leo had a fling in 1997 which leads us to believe they both got something from the hook up. Natasha was a model, which was Leo's "type" and after the split she became an actress. A pretty good one at that! Natasha nabbed him up after the premiere of "Titanic".

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Toni Garrn -- Apple To His Eye, Until She Wasn't!

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Toni Garrn, who is nearly two decades younger than Leonardo maintained a quiet relationship for almost two years. Although they had a lot of common interests, leaving a party with twenty girls was not one of them. This eventually led them to split and move on. Garrn is still found doing what she does best, modeling all over the world.

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Beauty -- Bar Refaeli and Leonardo Long Lasting?

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Another five year relationship bit the dust in 2011. This was a mutual break up as both parties were not ready to settle down. Their love for each other was not stronger than the temptation of different paths they were wanting to take. Imagine this, they are, of course, still friends. This was the point that Leo admitted he wasn't sure that he would ever tie the knot due to seeing so many marriages fail. It's rumored that Bar still tugs at Leo's heart.

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Bombshell, Blake Lively Briefly Dates Leonardo DiCaprio

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Bombshell Blake Lively dates Leo for a brief moment in 2011. At this point, you have to realized Blake is no model, although she could be, no doubt. Blake was post Bar and the only non-model he dated. Leo's family was devastated when their split hit the news. Apparently their love was no match for time and distance. Let's just hope the rumors aren't true that Blake was too busy spending time with now husband, Ryan Reynolds.

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Anne Vyalitsyna, Russian Model and Leo's Ex

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Anne V. is a Russian beauty queen and well known Victoria's Secret Model! It didn't take Leo long to become completely smitten by her looks and personality. Anne V. later went on to date Adam Levine, which is a complete opposite to Leo. Anne V. is now a mother, but still in fantastic shape.

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Sweet, Kelly Rohrbach and Leo Have a Whirlwind Romance!

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Kelly is one of the busiest Supermodels in the world and Leo had a new movie coming out. With schedules like theirs, how could you possibly stay invested in a relationship? Well, they definitely couldn't. They split in early 2016 and reassured the media that there was no one else on either end.

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Erin Heatherton, Another Victoria's Secret Model Bites The Dust!

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Leo and Erin dated briefly in 2012 and split because of their "busy schedules". This is another one of those relationships that he maintains as a friend with a lot respect. Erin did go on to meet Felix, and Australian musician who she feels at one with. She is the face of many big name brands.

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Laura Whitmore Took Leo's Breath Away

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Miss Laura was dating a rocker when catching Leo's eye. It didn't take long for her relationship to get complicated and become available for Leo. Laura stated nothing happened with Leo but that didn't prevent media from getting rumors started. They do look fitting for each other.

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Beautiful Blue-Eyed Victoria Robinson

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Leo took a turn for the wild side, the brunette side! Victoria is a beautiful model, but she is not blonde, like the others. There are known reasons as to why Victoria and Leo broke up. Nor is there a period of time that they were together. Maybe it was a one night stand, maybe it's another low-key relationship.

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Helena Christensen Cannot Confirm, but Hasn't Denied

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Helena and Leo never confirmed their love story, but they most certainly did not deny it either. Helena and Leo were seen together back in 1997 and their relationship has been left there. Clearly, two decades later, they have both moved on and right where they want to be. Since Helena, Leo has dated some of the most elite models known to the world.

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Work, Work, Work it Rihanna and Leo

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Relationship or friendship? Hardly anyone could tell. However, it was finally announced that neither one were looking for a relationship, but they sure did love running into each other on occasion. I have zero "break up" news because there is nothing to report.

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Bijou Phillips wasn't Leo's lady love

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Easy to say that things between Leo and Bijou did not end well. It was reported that she was quick to get over Leo and move onto Elijah Wood, who isn't the sight for sore eyes like Leo.It's a good thing this relationship is nearly twenty years old. You can still find Bijou absolutely stunning on film or print.

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Amber Valletta and her small fling with the Model King

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Amber's fling with Leo lasted so short that media found he was dating another model before anyone knew it. Amber wasn't heartbroken of course and was able to move on quickly. I'm not sure I would be able to move on from this hottie as quickly as Leo did. Amber is such a stunning woman, there is no doubt that she will find someone to sweep her off her feet.

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A Married Eva Herzigova and Leo?

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Eva Herzigova was reportedly married to Bon Jovi's drummer when the rumor mill started the relationship between her and Leo. There was no break up announced because neither party confirmed whether the relationship was factual. A married woman doesn't sound like Leo's cup of tea. Who is to say it did or didn't happen? I guess we will just never know.

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Oh Madalina Ghenea!

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Stunning Madalina and Leo had a brief relationship, if that's what you even want to call it in 2011 right after his brief relationship with Blake Lively. The hot fling lasted during the filming of The Great Gatsby and was over, much like the other, before anyone knew it. A few dinners and probably a few nightcaps, the relationship then ended before there was anything to report. I bet Leo kicks himself in the butt for letting this woman go.

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