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.
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.
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.
Helena Christensen: 1997 -
Danish model Helena Christensen and DiCaprio reportedly partied together when the blockbuster 'Titanic' came out.
Natasha Henstridge: 1997 -
Actress and model Natasha Henstridge also had a fling with the actor back in 1997.
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.'
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.
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).
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.
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.
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.
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...
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.
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.
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.
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.
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.