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Home Lipstiqle

Leo DiCaprio’s Dating History Is Crazy Long. Here’s His Trail Of Exes!

by Xuen-Li
June 24, 2025
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Leonardo DiCaprio’s dating life is almost as well known as his acting career and his activism. He has been involved with many women over the course of his life, so it’s safe to say that his dating life has been quite an eventful one. There’s even a running joke surrounding the women he’s dated and how they never seem to be over the age of 25. His dating stats say it all: young, blonde, and has been on a Victoria’s Secret runway. Reddit user u/TrustLittleBrother even made a chart that showed that DiCaprio has never dated women over the age of 25. In fact, the average age of his girlfriends is 22!

via Reddit u/TrustLittleBrother

More recently, he broke up with Camila Morrone, who he’d been dating since 2017, after she turned 25. The question remains: How many women has he dated, and who are they? Sit back, relax, because it’s a long list. Here’s the entire rundown:

Bridget Hall

The supermodel was spotted several times “canoodling” with DiCaprio around NYC in 1994. She was the first woman to be linked with him since he launched his movie career.

Naomi Campbell

It’s been reported that the supermodel hooked up with DiCaprio back in 1995, but decided to keep things platonic at the end. They’ve remained friends over the years, and have gone on vacations together with their group of mutual friends.

Kristen Zhang

They dated for a total of 15 months, between 1996 and 1997, just before he starred in “Titanic”. The model accompanied him to the premier of Romeo + Juliet. It was reported that the model broke up with the then 23-year-old actor because of his immaturity.

Helena Christensen

The Danish model was reportedly one of the first women that “partied” with DiCaprio after he shot to fame with Titanic in 1997. The former Victoria’s Secret Angel got together with “The Walking Dead” star Norman Reedus shortly after.

Amber Valletta

DiCaprio allegedly tracked the model down after he saw her picture in a magazine in 1998. The two then had a brief fling that year.

Eva Herzigova

DiCaprio reportedly dated Victoria’s Secret model Eva Herzigova for two months in 1998. This is unconfirmed though, as the Czech supermodel was married to Bon Jovi drummer, Tico Torres, at the time.

Bijou Philips

Daughter of singer John Phillips, Bijou dated Leo in 1998. She credited him with getting her the starring role in the 1999 drama “Black and White”.

Gisele Bündchen

The pair dated for 5 years, from 2000 to 2005. DiCaprio also attended the 2005 Oscars red carpet with the supermodel on his arm. She’s now married to NFL star Tom Brady.

Bar Refaeli

The couple had an on-again, off-again romance that lasted from 2005 to 2010 after meeting at a U2 concert in Las Vegas. Refaeli even took DiCaprio and his mom to visit her family in Tel Aviv to celebrate the actor’s 36th birthday.

Anne Vyalitsyna

The Catch Me If You Can star had a brief fling with the Russian Victoria’s Secret model during a break with Bar Refaeli. They met in Ibiza and were spotted getting close while hanging out on a yacht in 2009.

Blake Lively

DiCaprio began a whirlwind romance with Blake Lively in 2011, when they were spotted on a yacht sailing the south of France. The relationship only lasted for 5 months.

Madalina Ghenea

The actor was rumoured to have briefly dated the Romanian model after his split with Blake Lively. They met while he was shooting The Great Gatsby in Australia.

Erin Heatherton

He dated the Victoria’s Secret model for 10 months before breaking up in 2012. It was reported that they broke up due to their “crazy schedules” and that there was “no bad blood” between the two.

Toni Garrn

DiCaprio dated the 23-year-old Victoria’s Secret model for more than a year before they ended things in 2014. The pair were rumoured to have rekindled their romance in September 2017.

Kelly Rohrbach

The couple was first spotted when they rode bikes together in NYC in June 2015. However, they broke up in 2016 due to their “intense work schedules”.

Nina Agdal

It was reported that DiCaprio dated the Danish Victoria’s Secret model, who was 17 years his junior, in 2016. They were seen vacationing on a private island in the Bahamas and Montauk. The two broke things off in May 2017

Camila Morrone

DiCaprio was first linked to the Argentinian model in late 2017 when they were spotted shopping together at Barney’s in Los Angeles. Their 22 year age gap has led many to question their relationship. She then told the Los Angeles Times, “There are so many relationships in Hollywood – and in the history of the world – where people have large age gaps,” adding, “I just think anyone should be able to date who they want to date.” The two broke up in August of 2022 after 4 years of dating.

More on celebs? Read these:

Anna Jobling, Rosé, Suga And More Celeb Instagram Shots!

Gigi Hadid’s Weird Girl Aesthetic Is Taking Over TikTok!

blake livelyCamila MorroneErin Heathertongisele bundchenHelena ChristensenLeonardo DiCapriolipsticleNaomi Campbelltitanic
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