The Complete History of Leonardo DiCaprio's Model-Filled Love Life

14 models, 15 blondes, 4 actresses, one pop star, and Leo.

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From Victoria's Secret Angels to A-list actresses, all the women Leo's dated―or rumored to have dated―in his 41 years on this planet.

Bridget Hall

According to a 1998 gossip item in The London Sun, Leo dumped the model—his very first!—after a "night of love" she found disappointing. (They had been seen "canoodling around New York" in 1994, People reports.) Bridget told New York Magazine in 1998 that "nothing happened" between them.

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Brittany Daniel

According to The Sun, after an 18-year-old Brittany Daniel (of Sweet Valley High fame) seduced Leo on-screen in The Basketball Diaries, they dated off-screen in 1994.

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Naomi Campbell

Leo's 1995 rumored fling with Naomi Campbell reportedly fizzled fast, but they became good friends. More than 20 years later, they still get together to look hot on vacation, save Russian tigers, and photobomb 50 Cent.

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Kristen Zang

Kristen Zang, a model who dated Leo for two years (1996-1998), accompanied the actor to the premiere of Romeo + Juilet. Although a source told The New York Daily News that Kristen was "the love of his life," she dumped him because of his immaturity and "posse of young model-hounds."

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Helena Christensen

Leo and Victoria's Secret model Helena Christensen "partied" together post-Titanic release.

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Natasha Henstridge

Another one of Leo's party friends was Natasha Henstridge, a model-turned-actress whose big break was playing the lead in Species. They reportedly had a fling in 1997.

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Amber Valletta

As tabloid legend goes, Leonardo saw Amber in a magazine and had his reps track her down. They reportedly briefly dated in 1998.

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Bijou Phillips

The daughter of singer John Phillips, Bijou dated Leo in 1998. He hooked her up with her first big Hollywood connection, director James Toback, who cast Bijou in his film Black and White. Things ended with Leo, and she moved on to costar Elijah Wood.

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Eva Herzigova

Leo reportedly dated Victoria's Secret model Eva Herzigova in 1998. Their month-long affair was unconfirmed, perhaps because Herzigova was married to Bon Jovi drummer Tico Torres at the time.

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Gisele Bündchen

Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005. "We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best," she told Access Hollywood in 2009.

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Bar Refaeli

Leo moved on to another Victoria's Secret model, Bar Refaeli, who shared his passion for activism. They dated on-and-off from 2005-2011, with one six-month break in between.

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Anne Vyalitsyna

During that six-month break with Bar in 2009, Leo vacationed and "wooed" Russian Victoria's Secret model Anne V in Ibiza.

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Blake Lively

Leo's 2011 whirlwind romance with Blake Lively started out with domestic bliss. She baked for him—"Leo's never dated a girl who can cook," a source told Us Weekly at the time. "And he's smitten!" But it ended after just five months. Then Blake found Ryan Reynolds, and Leo found more models.

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Madalina Ghenea

After Leo's breakup with Blake, the actor was rumored to have briefly dated model Madalina Ghenea. They met while he was shooting The Great Gatsby in Australia.

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Erin Heatherton

Leo dated Victoria's Secret model Erin Heatherton for 10 months in 2012 until "crazy schedules" dragged them apart.

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Toni Garrn

After dating for over a year (starting in May 2013), Leo and 23-year-old Victoria's Secret model Toni Garrn broke up in 2014. Tabloids claimed Leo being seen leaving a Miami nightclub with 20 women contributed to the split.

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Kelly Rohrbach

Leo began dating Kelly Rohrbach, a former prep schooler, D1 golfer, Georgetown University grad, and yes, Sports Illustrated model, in the spring of 2015. In June, they were kissing on Citi Bikes. There were even rumors of an engagement! But Kelly and Leo didn't last: by the beginning of 2016, they had broken up.

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Rihanna

Leo and Rihanna apparently shared a "flirtatious" night in a Paris club in January, though tabloids reported the two had a fling going on long before. They were rumored to be dating in February 2015. Rihanna denied it then—she was too busy to date anyone—but said if she had the time, her guy "would have to be man enough to live with my schedule and not get scared." ...Leo?

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Laura Whitmore

At the BAFTAs earlier this month, Leo reportedly "plucked" Irish TV presenter Laura Whitmore out of an after-party crowd and was "all over her." (One source said he even invited her back to his hotel room.) Laura coyly addressed the rumor in Hello!, telling the outlet, "everyone was just having fun–there was a lot of dancing."

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