Every Single Woman Leonardo DiCaprio Dated, May Have Dated, or Definitely Did Not Date

Every Single Woman Leonardo DiCaprio Dated, May Have Dated, or Definitely Did Not Date
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Another day, another model linked to Leonardo DiCaprio—and while Leo keeps getting older, the ladies just keep getting younger.

This week, it’s 24-year-old Sports Illustrated model Nina Agdal who was spotted “lounging” with the actor in Montauk, New York. Witnesses told TMZ that the pair smoked for a few hours in the lounge area at The Crows Nest restaurant before heading inside for dinner, and they were seen getting breakfast at Goldberg’s Famous Bagels. This all sounds pretty PG-13, and a source told People that the pair isn’t romantically involved, but then again this is Leo we’re talking about.

Last month a different woman—23-year-old Ford model Victoria Lee Robinson—was seen leaving Justin Bieber’s Purpose tour after-party in New York City with DiCaprio. Weeks before that it was 24-year-old Instagram star Roxy Horner on Leo’s arm, and recently the toxic bachelor was reportedly wooing 19-year-old model Chelsey Weimar. Before that? Rihanna, Kelly RohrbachErin Heatherton, Toni Garrn–hell, you name a model, and we’d safely bet she’s linked with DiCaprio. The guy’s nothing if not consistent.

MORE: The 40 Most Naked Celebrity Instagrams of All Time

In the slideshow ahead we’ve rounded up every woman Leo’s dated, may have dated, and probably didn’t date (but we all wildly speculated about anyway). At least these ladies, from Gisele Bündchen to Blake Lively, are in good company.

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Bridget Hall

You're looking at her, folks: Leo's very first! (Model, that is.) He didn't get off to a smooth start, either: A gossip column ran in a 1998 edition of The London Sun, saying that the couple ended things after Leo failed to call the model when she lost her virginity to him in a "night of love." It, and other articles around the same time, note that Hall found the sexual encounter "disappointing"—the Globe even quoted her as saying "he was lousy in bed." Hall later denied that anything happened between them in an interview with New York Magazine.

Photo: Getty Images

Claire Danes

Ever since "Romeo and Juliet" dropped in 1996, fans have speculated that Claire Danes and Leonardo DiCaprio were a couple IRL too. However, this rumor has gone completely unconfirmed and seems pretty unlikely.

Photo: Wenn

Brittany Daniel

You might remember Brittany Daniel seducing a 20-year-old Leo in "Basketball Diaries"–well, apparently that happened in real life too. Leo was thought to be dating the "Sweet Valley High" star after they met on set.

Photo: Wenn

Naomi Campbell

In keeping with his supermodel theme, Leo was rumored to have had a fling with Naomi Campbell in 1995.

Photo: Wenn

Kristen Zang

Another model, Kristen Zang, dated Leo from 1996 until 1998. She reportedly ended things because he wouldn't ditch his "posse of young model-hounds." Ah, nostalgia.

Photo: Getty Images

Helena Christensen

She's happily coupled up with musician Paul Banks now, but back in his "Titanic" days, Leo and Helen Christensen were rumored to have a fling.

Photo: Wenn

Natasha Henstridge

Back in 1997, Henstridge and Leo were rumored to be dating.

Photo: Wenn

Amber Valletta

Like a true diva, Leo apparently saw the blonde model in a magazine and had his people get in touch. They're said to have dated for a little while in '98.


Photo: Wenn

Bijous Phillips

John Phillips's daughter, Bijous, had a romance with DiCaprio in 1998.

Photo: Wenn

Eva Herzigova

Probably one of Leo's most scandalous (rumored) hook-ups is Eva Herzigova. Tabloids were speculating that the pair was seeing each other back in 1998—while the model was married to Bon Jovi drummer Tico Torres.

Photo: Wenn

Gisele Bündchen

She might be married now, but before Tom Brady, Gisele and Leo were an item for a whopping five years—pretty serious by DiCaprio standards. They broke up in 2005.

Photo: Wenn

Bar Refaeli

Another day, another Victoria's Secret model. This time, Leo dated Refaeli on and off from 2005 through 2011.

Photo: Wenn

Blake Lively

Blake Lively's romance with Leo in 2011 ended after just five months!

Photo: Wenn

Alyce Crawford

Days after splitting with Blake Lively, Leo was linked with 21-year-old Australian model Alyce Crawford. He was in Sydney at the time filming "The Great Gatsby" and was said to be having "regular visits" from the former "Australia's Next Top Model" contestant.

Photo: Wenn

Madalina Ghenea

Ghenea met Leo while he was filming "The Great Gatsby" in Australia, and they're rumored to have dated for a little while afterward.

Photo: Wenn

Erin Heatherton

After 10 months together, Victoria's Secret model Erin Heatherton and Leo called it quits, citing scheduling conflicts as the cause. Romantic.

Photo: Wenn

Toni Garrn

Yep, another Victoria's Secret model. This time, they dated for more than a year, eventually breaking up in 2014.

Photo: Wenn

Kelly Rohrbach

According to multiple reports, Leo, 41, and Sports Illustrated model Kelly Rohrbach, 25, split in early 2016 after being spotted out together on numerous occasions over the previous year. There was even speculation that Rohrbach and DiCaprio were engaged—but it clearly wasn't meant to be. “They’ve been broken up for over a month. It was mutual. They both have intense work schedules and a lot going on in their lives right now. They both needed to take a break because of that. They are still friends and talking but it’s over,” a source told Us Weekly.

Photo: Wenn


We're not buying this one, but we couldn't run a guide to Leo's dating history without including Rihanna. Apparently the pair has been spotted hooking up all over the place—at the Playboy Mansion (where we assume Leo spends most weekends), Paris, and possibly even at Coachella in 2016.

Photo: Wenn

Chelsea Weimer

According to Page Six, “spies” said the pair was spotted leaving Nobu Malibu (obviously) together, and she recently shared Instagram shots that are apparently taken at Leo’s homes in L.A. How people know this, we have no idea. Another source denied the claims to the tabloid, saying Leo’s way too busy saving the planet to have time for models: “It’s not true. He isn’t spending time with anyone. Most of his time lately has been in places like Indonesia, trying to help save the ecosystem.”

It’s hard to find Weimar’s actual age, but it looks as though she’s well within DiCaprio’s early-20s age requirement for girlfriends, with some reports pegging her as 19 years old and others saying she’s 20. Leo gets older, but the women just keep getting younger.

Laura Whitmore

Earlier this year at the BAFTAs, Leo was reportedly "all over" the Irish TV presenter. Whitmore addressed the rumor in an interview with Hello!, simply saying that "everyone was just having fun—there was a lot of dancing."

Photo: Wenn

Roxy Horner

If you haven’t heard of Horner, don’t worry: You’re not the only one—she's an Instagram-famous model who Page Six said that “spies” spotted with Leo on a double date in New York in April 2016. They were on a double date with the actor’s BFF Lukas Haas (who is 40) and some other blonde girl (who is likely under the age of 25).

Victoria Robinson

This 23-year-old model was spotted leaving Justin Bieber’s 2016 Purpose concert in New York with Leo. It probably would have been more age appropriate to leave with Justin, but no judgment.

Nina Agdal

DiCaprio was spotted lounging with Sports Illustrated swimsuit model Nina Agdal in June at the Crow's Nest in Montauk, New York.

Photo: Wenn

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