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Leo's List of Lovers Revealed: 48 Women Named in DiCaprio's Secret Conga Line of Hook-Ups!

women in leonardo dicaprios dating history
Source: MEGA

Sep. 12 2023, Published 7:30 a.m. ET

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Bridget Hall

bridget hall
Source: MEGA

Leonardo DiCaprio's dating spree started in 1994 with Bridget Hall. According to People, they were spotted canoodling around New York, but the actor reportedly dumped her after she found their "night of love" disappointing.

Hall clarified the reports and told New York Magazine that The London Sun's 1998 gossip was untrue and that nothing happened between them.

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Britanny Daniel

britanny daniel
Source: MEGA

DiCaprio immediately moved on with his The Basketball Diaries costar Brittany Daniel after his split from Hall. Per The Sun, they dated off-screen but never addressed their romance.

Naomi Campbell

naomi campbell
Source: MEGA

Naomi Campbell and DiCaprio are currently good friends, but they had a brief fling in 1995 ahead of the release of his hit film Titanic.

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Kidada Jones

kidada jones
Source: MEGA

The Parenthood actor sparked dating rumors with Kidada Jones in 1999 after her engagement with Tupac Shakur ended following the rapper's tragic murder.

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Claire Danes

claire danes
Source: MEGA

DiCaprio and Claire Danes followed their Romeo + Juliet characters' love story and had a real-life fling.

The actress revealed in her interview with W Magazine that her romantic interest in the actor was problematic.

"I couldn't really have a crush on the guy I was professionally having a crush on!" she said. "Quite a few gay men have talked to me about the fact that when they were kids watching Romeo + Juliet, they were confused about who they wanted to kiss. It was all about Leo! And I completely understand."

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Kristen Zang

kristen zang
Source: MEGA

Although the actor was linked to Danes, he took Kristen Zang as his date to the Romeo + Juliet premiere in Los Angeles instead. They dated from 1996 to 1997.

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Helena Christensen

helena christensen
Source: MEGA

DiCaprio chose Helena Christensen as the woman to hook up with around Titanic's release.

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Demi Moore

demi moore
Source: MEGA

Demi Moore reportedly hooked up with DiCaprio in 1997 as her marriage to Bruce Willis started to hit rock bottom. They were spotted having a dinner amid her marriage troubles.

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Vanessa Trump

vanessa trump
Source: MEGA

Due to Titanic's success, more women got linked to the DiCaprio – including Donald Trump Jr.'s ex-wife Vanessa Trump.

New York Magazine published a report about their outing in a New York City nightclub, but DiCaprio's representative dismissed the rumors. Eventually, news outlets exposed her as the one who fed the story to a gossip writer and claimed DiCaprio was happy he was with someone who was so down to earth.

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Natasha Henstridge

natasha henstridge
Source: MEGA

In 1997, DiCaprio reportedly had another brief fling with one of his party friends Natasha Henstridge.

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Amber Valletta

amber valletta
Source: MEGA

A tabloid claimed that DiCaprio started pursuing Amber Valletta after seeing her in a magazine. He reportedly asked his representatives to track her down and connect him with her.

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Bijou Phillips

bijou phillips
Source: MEGA

Bijou Phillips dated DiCaprio in 1998, and DiCaprio played a huge role in connecting her with Hollywood director James Toback, who soon cast her in the film Black and White.

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Liv Tyler

liv tyler
Source: MEGA

Aerosmith frontman Steven Tyler's daughter Liv Tyler ignited romance rumors with the This Boy's Life actor after photos of them at a late '90s party spread.

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Eva Herzigová

eva herzigova
Source: MEGA

Czech supermodel Eva Herzigová stole DiCaprio's heart when they met at the Man in the Iron Mask premiere in 1998, and they had a two-month affair while she was married to Bon Jovi drummer Tico Torres.

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Virginie LeDoyen

virginie ledoyen
Source: MEGA

DiCaprio targeted another costar when he met Virginie LeDoyen on the set of the 2020 film The Beach, in which they played lovers.

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Gisele Bündchen

gisele bundchen
Source: MEGA

The Catch Me If You Can star finally had a long relationship when he met and dated Gisele Bündchen. Their relationship lasted only five years until 2005.

In her interview with Vanity Fair in 2009, she revealed they were not meant to be boyfriend and girlfriend.

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Bar Refaeli

bar refaeli
Source: MEGA

DiCaprio had another lengthy romance with Victoria's Secret model Bar Refaeli from 2005 to 2011, though their relationship was on-again, off-again over the years.

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Anne Vyalitsyna

anne vyalitsyna
Source: MEGA

Swimsuit model Anne Vyalitsyna met DiCaprio in Ibiza when he broke up with Refaeli. News outlets caught them getting close while enjoying a trip on a yacht in 2009.

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Blake Lively

blake lively
Source: MEGA

Another yacht love story: DiCaprio's romance with Blake Lively started in 2011 while they sailed in the south of France. Their relationship lasted only five months, and they ultimately moved on from their failed fling.

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Paris Hilton

paris hilton
Source: MEGA

DiCaprio also had a brief romance with American socialite Paris Hilton from September 2000 to November 2000.

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Mădălina Ghenea

madalina ghenea
Source: MEGA

In 2011, The Great Gatsby filmed in Australia, leading him to meet Mădălina Ghenea. Their relationship only lasted only a few dinners.

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Erin Heatherton

erin heatherton
Source: MEGA

In 2012, Erin Heatherton and DiCaprio dated for ten months and broke up because of their schedules.

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Margarita Gauchet

margarita gauchet
Source: MEGA

The Gardener of Eden actor added a young model to his relationship history as they sparked romance rumors in 2013. DiCaprio reportedly asked Jonah Hill for her number, and he soon invited her to his New Year's yacht party in Australia.

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Alyce Crawford

alyce crawford
Source: @alycecrawford/Instagram

DiCaprio and Alyce Crawford's romance rumors emerged in 2011 — but disappeared as quickly as they started.

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Miranda Kerr

miranda kerr
Source: MEGA

DiCaprio and Miranda Kerr became close when they hung out in 2013. At that time, the model had just split from Orlando Bloom.

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Alesia Riabenkova

alesia riabenkova
Source: MEGA

DiCaprio sparked rumors that he dated Alesia Riabenkova in 2013, though no further reports surfaced afterward.

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Toni Garrn

toni garrn
Source: MEGA

Toni Garrn broke DiCaprio's dating spree with young models in 2013. They marked one of their first outings as a couple at the 66th Cannes Festival but broke up the following year.

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Rihanna

rihanna
Source: MEGA

Dating rumors between DiCaprio and Rihanna began in February 2015, but the singer denied it. The rumors resurfaced in January 2016 when the public spotted them having a flirtatious night in a Paris club.

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Kelly Rohrbach

kelly rohrbach
Source: MEGA

In 2016, DiCaprio and Kelly Rohrbach called it quits after dating for months. h

"They both have intense work schedules and a lot going on in their lives right now," a source told Us Weekly. "They are still friends and talking but it's over."

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Roxy Horner

roxy horner
Source: MEGA

DiCaprio was spotted with another model in 2016.

Roxy Horner grabbed dinner with the star in New York City.

A source told People that the model was attached to DiCaprio and that they were affectionate. However, the romance rumors ended after she revealed in since-deleted tweets that they were just friends.

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Ela Kawalec

ela kawalec
Source: @ela.kawalec/Instagram

DiCaprio and Polish model Ela Kawalec enjoyed a bike date around New York City before he attended Cannes in May 2016. Prior to their day outing, the duo reportedly attended a birthday celebration at Marquee, where they were spotted looking like a couple.

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Chelsey Weimar

chelsey weimar
Source: @chelsey_weimar/Instagram

Another model appeared on DiCaprio's dating list: Chelsey Weimar.

Page Six cited sources who claimed they saw the duo leaving Nobu Malibu together and that Weimar went to his Los Angeles home based on the photos she shared on Instagram.

Another insider dismissed the rumor and said the report about their relationship was not true.

"He isn't spending time with anyone," said the source. "Most of his time lately has been in places like Indonesia, trying to help save the ecosystem."

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Laura Whitmore

laura whitmore
Source: MEGA

DiCaprio reportedly flirted with Laura Whitmore after they met at the 2016 BAFTAs following an after-party. One source claimed he invited her to his hotel room.

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Victoria Lee Robinson

victoria lee robinson
Source: @victorialeerobinson/Instagram

DiCaprio's flirting stage with Ford model Victoria Lee Robinson seemingly started when they attended Justin Bieber's Purpose tour in 2016. It is unclear how long they were together or if their relationship progressed.

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Georgia Fowler

georgia fowler
Source: MEGA

After his outing with Robinson, DiCaprio was spotted with model Georgia Fowler at a Cannes Film Festival party, though the rumors stopped days after the event.

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Nina Agdal

nina agdal
Source: MEGA

DiCaprio started a new romance with Nina Agdal in the summer of 2016. However, they reportedly split after their brief romance but remained friends.

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Ella Ross

ella ross
Source: @ellarossalina/Instagram

As soon as DiCaprio called it quits with Agdal, he sparked romance rumors with Ella Ross. The model previously dated Kourtney Kardashian's ex Scott Disick.

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Lorena Rae

lorena rae
Source: MEGA

DiCaprio was spotted with model Lorena Rae in August 2017, leading to dating rumors. The buzz eventually stopped after DiCaprio's representative denied their reported romance.

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Camila Morrone

camila morrone
Source: MEGA

DiCaprio had one of his "most serious" connections with Camila Morrone.

The couple was first spotted at Barney's in Los Angeles in December 2017, but their relationship also attracted criticism because of their more than two-decade age gap.

However, the model soon defended their romance in her interview with the Los Angeles Times.

"There's so many relationships in Hollywood — and in the history of the world — where people have large age gaps," she said. "I just think anyone should be able to date who they want to date."

However, they broke up in August 2022 after four years of dating.

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Gigi Hadid

gigi hadid
Source: MEGA

In September 2022, Gigi Hadid and DiCaprio sparked dating rumors after being spotted on an outing. Their dates continued until they broke up in February.

"She hasn't seen him for a while. She just decided that she was done with him," a source told People. "They are at very different places in life. She prioritizes being a mom. It was never that serious anyway."

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Victoria Lamas

victoria lamas
Source: @victoriaalamas/Instagram

While dating Hadid, DiCaprio had another romance rumor with Victoria Lamas after they grabbed dinner at The Bird Streets Club. They left the restaurant separately but soon got into the Oscar winner's car together.

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Eden Polani

eden polani
Source: @edenpolanii/Instagram

After DiCaprio's romances with Hadid and Lamas, new relationship rumors emerged after DiCaprio was photographed getting close to Eden Polani at Ebony Riley's music release party.

However, the buzz did not last long.

"Leo and Eden just so happen to have been seated next to each other at the party and were hanging in the same group," a source told E! News. "Just because Leo might be talking to or sitting with a girl doesn't mean he's dating her."

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Meghan Roche

meghan roche
Source: MEGA

DiCaprio's fling list grew with Meghan Roche.

The rumored couple were spotted boarding a yacht in Ibiza with DiCaprio's other friends, and she appeared to be the only woman in the group.

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Neelam Gill

neelam gill
Source: MEGA

Neelam Gill sparked speculation that she and DiCaprio were an item. Photos taken during their vacation in a yacht and dinner dates surfaced in July, but she clarified on Instagram hours later that she was not the handsome hunk's new flame.

"In fact, I am in a committed relationship with his good friend, and have been for many months now," she said. "The only reason we have been pictured in the same vicinity is because I have been there with my partner."

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Rose Bertram

rose bertram
Source: MEGA

The Academy Award-winning actor started a series of flings over the past few months, including one with Rose Bertram. The Belgian model supposedly spent a night with DiCaprio, alongside another woman who was also linked to him.

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Maya Jama

maya jama
Source: MEGA

Maya Jama was with Bertram and DiCaprio when they snuck out of a bar, and she became the subject of her own romance rumors.

She previously responded to other buzz that exploded earlier this year, asking everyone to stop since they were not dating.

"I've been minding my business on holiday & said I wouldn't respond/pay attention to any of the silly stories anymore but you need to stop now," the Love Island host wrote on X, formerly known as Twitter.

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Irina Shayk

irina shayk
Source: MEGA

Bradley Cooper's ex Irina Shayk sparked rumors she was dating DiCaprio after they mingled at Levi and Don Julio's Neon Carnival event. Their representatives did not clarify their relationship, but they have been longtime friends before the rumors broke.

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Vittoria Ceretti

vittoria ceretti
Source: MEGA

DiCaprio was spotted canoodling with another young model as of late.

The young beauty, confirmed to be 25-year-old Italian model Vittoria Ceretti, sparked dating rumors with DiCaprio after they were spotted kissing at the Hi Ibiza club in Ibiza, Spain. A source told Daily Mail that the duo has been dating for at least two months now.

"It has obviously led to much chatter within his circle that Leo is ready to hang up his lothario ways," the unnamed insider said. "There have been many women pictured with him, partying with him, but what he has with Vittoria is much more serious."

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