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Kate Moss: 1994 -

The actor and the British model dated back when they were only 20 years old. They weren't really serious about the relationship. 

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Bridget Hall: 1994 -

The young model was also linked with DiCaprio back in 1994. It's reported that she was the first Victoria's Secret model he ever dated. However, Hall told New York Magazine in 1998 that "nothing happened" between them.

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Brittany Daniel: 1994 -

You might remember Brittany Daniel from the teen drama 'Sweet Valley High.' Co-star to DiCaprio in 'The Basketball Diaries' (1995), the pair dated off-screen in 1994.

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Naomi Campbell: 1995 -

It has long been reported that something went on between the supermodel and the actor back in 1995. Nonetheless, they've stayed close friends over the years. 

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Kristen Zang: 1995-1999 -

DiCaprio later went out with actress and model Kristen Zang. They broke up in 1997, before getting back together, and ending things for good in 1999. She was 25 when she broke up with him.

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Helena Christensen: 1997 -

Danish model Helena Christensen and DiCaprio reportedly partied together when the blockbuster 'Titanic' came out.

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Natasha Henstridge: 1997 -

Actress and model Natasha Henstridge also had a fling with the actor back in 1997. 

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Eva Herzigová: 1998 -

DiCaprio had a two-month fling with the Czech model, after meeting at the premiere of 'The Man in the Iron Mask.'

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Amber Valletta: 1998 -

The story goes that DiCaprio spotted model Amber Valetta in a magazine and was totally smitten. He had his staff arrange a meeting and they briefly dated.

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Bijou Phillips: 1998 -

Bijou Phillips, the daughter of singer John Phillips, dated DiCaprio in 1998. She later credited him for getting her a role in the movie 'Black and White' (1999).

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Virginie LeDoyen: 1999 -

DiCaprio met the French actress on the set of 'The Beach' (2000), where their on-screen romance briefly came to life while filming.

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Gisele Bündchen: 1999 to 2005 -

The pair dated on and off for six years from 1999 through 2005, becoming one of Hollywood's most private couples.

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Gisele Bündchen: 1999 to 2005 -

In her book 'Lessons' (2018), the Brazilian model opened up about how she decided to break up with him. She was 25, while he was 31. "No longer numbing myself with smoking, drinking, and too much work, I was becoming more and more aware of things that I'd chosen not to look at." She continued, "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes."

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Bar Refaeli: 2005-2011 -

After Bündchen, the actor moved on to another Victoria's Secret talent, Israeli model Bar Refaeli, whom he met at a U2 concert in Las Vegas. 

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Bar Refaeli: 2005-2011 -

They dated on and off from 2005 to 2011, with one six-month break in between. DiCaprio was 36 and Refaeli was 25 (what else?) when they broke up. 

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Anne Vyalitsyna: 2009 -

During one of his many breakups with Bar Refaeli, DiCaprio had a short romance with Anne Vyalitsyna, another Victoria's Secret model. The two were spotted together in Ibiza. 

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Blake Lively: 2011 -

Blake Lively and DiCaprio only dated for five months in 2011, she was 26 at the time. She then found Ryan Reynolds, and DiCaprio found more models.

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Mădălina Ghenea: 2011 -

After his breakup with Lively, the actor was rumored to have briefly dated Romanian model Mădălina Ghenea. They met while he was shooting 'The Great Gatsby' (2013) in Australia.

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Erin Heatherton: 2012 -

The then 37-year-old actor and the 23-year-old model dated for 10 months in 2012. Their crazy schedules dragged them apart.

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Toni Garrn: 2013-2014 -

In May 2013, the actor met another model. This time it was the 23-year-old Victoria's Secret model Toni Garrn. They split after about a year, which may or may not have happened after he was seen leaving a Miami nightclub with 20 women.

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Kelly Rohrbach: 2015 -

DiCaprio and the Sports Illustrated model, who share an age difference of 16 years, split after a few months of dating. She was 25...

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Rihanna: 2016 -

Sources denied they were an item, but this didn't stop the rumors. They were spotted being very close at Coachella in 2016, which came just a year after they were reportedly seen kissing at a Playboy Mansion party.

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Georgia Fowler: 2016 -

Shortly after, DiCaprio was spotted getting close with the 23-year-old model at a Cannes Film Festival party. However, romance rumors died down. 

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Nina Agdal: 2016 to 2017 -

DiCaprio and Danish model Nina Agdal, who previously dated Adam Levine, began their romance in the summer of 2016. They were seen vacationing together in Montauk, New York, and the Bahamas. The pair broke up in 2017, when Agdal was 25 years old. 

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Lorena Rae: 2017 -

In August 2017, the 41-year-old actor was linked to 23-year-old model Lorena Rae. They were spotted on several globe-trotting dates, from Monaco to St. Tropez, and New York City. Rumors of any further dating eventually quieted down.

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Camila Morrone: 2017 to 2022 -

Dating rumors with the Argentine-American actress started around December 2017. With a 22-year age gap, Camila Morrone was only 20 when they stared dating. 

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Camila Morrone: 2017 to 2022 -

The pair called it quits in 2022 after over four years together. Morrone had just turned 25. 

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Gigi Hadid: 2022 -

The pair were first linked back in September 2022. However, things seemed to have quickly fizzled by early 2023. Maybe the fact that she was 27 had something to do with it.

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Vittoria Ceretti: 2023 -

In August 2023, the actor was spotted out and about with model Vittoria Ceretti. The Italian beauty is 25 years old, of course. 

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Kate Winslet -

Tricked you there! Contrary to popular belief, the actors have never dated each other. Ever since 'Titanic' (1997), they've been close friends. 

Sources: (People) (Elle) (Cosmopolitan) (Page Six)

See also: Kate Winslet and Leonardo DiCaprio's adorable friendship

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