20 Women Leonardo DiCaprio Has Been Lucky Enough to Have on His Arm

Rumors have surfaced that timeless babe Leonardo DiCaprio left a club with 20 women on his arm, which actually sounds... kind of plausible. Let's face it, DiCaprio is constantly riding waves that primarily consist of statuesque blonde beauties. Most of them models, some rumored flings, some confirmed girlfriends. And hey, let's not forget the other two most important women in his life, the ones he's, you know, not involved with romantically.

On the one hand, I have to admit that I'm morally against that kind of philandering, and when I see behavior like that in real life I'm entirely repulsed. On the other hand, it's Leo. I mean...

Let's just indulge ourselves, if only for a moment, and rehash 20 women that are a part of the Leonardo DiCaprio legend, be it footnotes, chapters or long story arcs.

Bridget Hall

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DiCaprio may-or-may-not have de-virginized this stunning blonde supermodel, the first in a series of many. It also may-or-may-not have been, according to Hall, “disappointing.”

Brittany Daniel

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They met on the set of The Basketball Diaries, which, having no love for sports, is something I have never watched.

Kate Moss

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They partied together and may have had a fling in the early ’90s. Can you even imagine?

Naomi Campbell

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Queen of the catwalk Campbell was romantically entangled with DiCaprio on a short-term basis, before settling for being platonic yachting buddies years later.

Claire Danes

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Some rumors say that Danes and DiCaprio dated while working on the set of Romeo + Juliet, while others insist they didn’t get along at all, and that Danes thought him to be “immature.”

Kristen Zang

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Another blonde model, and maybe not a forever thing, but the two were spotted at the premiere of Romeo + Juliet.

Kate Winslet

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Sadly Jack and Rose ending up together will only remain the stuff of fanfiction, but at least Winslet and DiCaprio have one of the sweetest and most enduring friendships in Hollywood.

Helena Christensen

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Christensen is another model who may have hooked up with DiCaprio Post-Titantic.

Bijou Phillips

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Phillips credits DiCaprio for helping her get a role in Black and White, which opened all the doors to her acting career and helped her become the Elizabeth Taylor of our time. Duh.

Demi Moore

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They may have had a fling in 1997 while she was still with Bruce Willis. Who am I to judge?

Amber Valletta

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Legend has it that DiCaprio was flipping through like, a copy of Vogue , thought she was hot, and arranged to be introduced to her. Like he was picking out a tank top in a Delia’s catalogue or something. Yuck.

Kidada Jones

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As in, Quincy Jones and Peggy Lipton’s eldest daughter, sister to one Rashida Jones. Allegedly, she and DiCaprio were an item for a time in the late ’90s.

Gisele Bundchen

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Duh. Before she settled for Tom Brady (who, to my understanding, plays football) she was involved in probably one of his longest-standing relationships.

Bar Refaeli

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This, also a pretty long-term relationship on DiCaprio’s part, is a substantial follow-up to Bundchen, no?

Blake Lively

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The two dated casually for about five months. Then, of course, she ended up with Ryan Reynolds, which I guess is a fair consolation prize.

Katie Cleary

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Yes, a model, and barely a blip on the record. Apparently, her and DiCaprio were friends and had been seen partying together. Then, under the stress of marital issues, her husband committed suicide. People were quick to link those two events, which is unfair to all involved, and a pretty dark chapter in our story.

Alyce Crawford

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An alleged companion during the filming of The Great Gatsby.

Erin Heatherton

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Plot twist: DiCaprio dates a Victoria’s Secret angel.

Toni Garrn

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Once again, he really wanted to change things up, so he decided to date a tall, blonde lingerie model.