Leonardo DiCaprio Dated Who?! 17 of Leo's Exes You Completely Forgot About

Leonardo DiCaprio is well known as one of Hollywood's eternal bachelors. Much like fellow movie star George Clooney, this guy has dated half of Hollywood and is currently making his way through the other half. Hey, no judgements here, Leo... it's just a lot of women to remember. And just in case you DiCaprio enthusiasts have forgotten who the Wolf of Wall Street star has allegedly stepped out with, fear not: Here's the crash course for the X lovely ladies that Leo has allegedly dated.

by Kaitlin Reilly

Bridget Hall

Hall and DiCaprio were seen “canoodling around New York” in 1994. Not exactly a grand romance, but she could say that she hung out with Jack Dawson years before he ever died hanging off of that raft.

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Erin Heatherton

The Victoria’s Secret model dated DiCaprio for 10 months from 2011 to 2012.

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Naomi Campbell

Surprised? Back in the 90s, DiCaprio and Campbell had a “brief fling” before deciding that they were better off as friends.

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Bijou Phillips

The daughter of Mamas and Papas singer John Philips allegedly dated DiCaprio as a teenager in the 90s.

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Demi Moore

Moore and DiCaprio allegedly “spent time together” in 1997, when Moore was getting out of her marriage with Bruce Willis.

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Eva Herzigova

According to People Magazine, Herzigova had an alleged tryst with DiCaprio in 1998 — while she was still married to Bon Jovi drummer Tico Torres. Neither have confirmed the relationship.

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Helena Christensen

Christensen and DiCaprio allegedly dated around the time that Titanic hit theaters in 1997. The fling was brief, probably because there were a lot of models on DiCaprio’s list at the time.

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Kristen Zang

DiCaprio and Zang allegedly dated on and off from 1996 to 1997, and even took the model (because of course she’s a model) to the premiere of Romeo & Juliet in 1996.

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Gisele Bündchen

If you’re going to date a Victoria’s Secret model, make it THE Victoria’s Secret model. (Or, if you’re like DiCaprio, just date all of the Victoria’s Secret models. You know, so you have all of your bases covered.) DiCaprio and Bundchen allegedly dated from 2001 to 2005 before splitting up.

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Claire Danes

You may want to file this relationship under “rumor,” because multiple sources have stated that Danes and DiCaprio didn’t even like one another on the set of Romeo & Juliet, the film that allegedly brought them together for a year-long relationship. Then again, Rachel McAdams and Ryan Gosling didn’t get along on the set of The Notebook, either, so what does that prove?

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Blake Lively

The former Gossip Girl star is now married to Ryan Reynolds, but prior to her relationship with her Green Hornet co-star, she was spotted with DiCaprio. Lively and DiCaprio allegedly dated for five months in 2011 before calling it quits.

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Kendal Schuler

The Australian model was allegedly seen spending time with DiCaprio after his split from actress Lively in 2011.

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Amber Valletta

DiCaprio allegedly saw a picture of then-model and current Revenge actress Valletta in a magazine and had his “people” track her down for a date. If you think that’s total creepy, remember that this was back in the 90s before Tinder was a thing.

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Bar Refaeli

Refaeli and DiCaprio dated on and off for six years before splitting in 2011, allegedly because neither wanted to “settle down.”

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Anne Vyalitsyna

Famously known as Adam Levine’s ex, Vyalitsyna and DiCaprio allegedly spent some time together during his break with Refaeli in 2009.

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Ashley Roberts

The Pussycat Doll partied with DiCaprio in Madrid in 2009, and the press called Roberts DiCaprio’s “rebound girl” from his split from Refaeli. Refaeli and DiCaprio reunited later that year.

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Toni Garrn

The 22-year-old Victoria’s Secret model (she inked that contract in 2011) has allegedly been dating DiCaprio since May 2013. Think that the notorious modelizer has finally settled down and become a one-model man? My fingers are crossed for you, Garrn.

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