Has Leonardo DiCaprio Ever Dated Anyone Over 25 Years Old?


When you’re a famous celebrity, plenty of legends get attached to you. Some of them are wild urban legends (removed ribs, anyone?), but some are a bit closer to reality. And one such legend concerns Leonardo DiCaprio.

As an actor, DiCaprio has a string of amazing movies to his name. Many of these films, including early hits like Romeo + Juliet and Titanic, are all about DiCaprio’s character finding love. Of course, his relationships were really doomed in those two movies, and maybe that should have been our first hint at Leo’s unlucky love life.

You see, DiCaprio never has trouble finding a new lover. But he seems completely incapable of staying in a relationship after a woman turns 25. And we couldn’t help but ask: has Leonardo DiCaprio ever dated anyone over 25 years old?

Let’s find out!

Bridget Hall: 16

When DiCaprio’s career started popping off in 1994, he was dating Bridget Hall.

However, they split up when she was 16 and Leo himself was 19.

Maybe she was his original star-crossed lover?

Naomi Campbell: 24

With Naomi Campbell, DiCaprio enjoyed more of an alleged fling than a true relationship in 1995.

They called it quits when DiCaprio was 20 and Campbell was 24.

Is this the earliest emergence of the dating pattern?

Kristen Zang: 22

Even Leonardo DiCaprio can be a victim of his own success. For example, he enjoyed a nice relationship with Kristen Zang between 1996 to 1997.

However, they broke up when each was 22 years old in part because of DiCaprio’s post-Titanic fame.

Eva Herzigová: 24

DiCaprio is rumored to have met Czech model Eva Herzigová at the premiere of his film The Man in the Iron Mask.

They had a brief fling in 1998 but split up when he was 23 and she was 24.

Gisele Bündchen: 24

After all these short-lived romances, DiCaprio seemed pretty serious with Gisele Bündchen.

They dated between 2000-2005, but they split when he was 30 and she was 24.

Still, she ended up marrying Tom Brady, and that’s not a bad consolation prize!

Bar Refaeli: 25

After Gisele Bündchen, DiCaprio entered another long-term relationship, this time with Israeli model Bar Refaeli.

He and Refaeli dated between 2005-2011, although they split for a few months in 2009 before getting back together.

They split for good once Refaeli turned 25 and DiCaprio was 36.

Yes, that means they began dating when Refaeli was 19 and DiCaprio was 30.

Blake Lively: 24

After Refaeli, DiCaprio briefly dated Blake Lively in 2011 (talk about the world’s best rebound).

They met on Steven Spielberg’s yacht, but even movie magic couldn’t keep these two together.

When they split, Lively was 24 and DiCaprio was 36.

Erin Heatherton: 23

Erin Heatherton’s name may not ring a bell, but DiCaprio seemed happy dating this Victoria’s Secret model for about 10 months in 2012.

By the time this angel flew away, she was 23 and DiCaprio was 37.

Alesia Riabenkova: 21

It was never fully confirmed if DiCaprio dated model and actress Alesia Riabenkova in 2013.

If they did date and break up that year as rumored, she would have been 21 and he would have been 38.

Toni Garrn: 22

What can we say: DiCaprio likes to date models.

He dated model Toni Garrn for one year after meeting her at the 66th Cannes Film Festival in 2013.

When they split, she was 22 and he was 40.

Kelly Rohrbach: 25

Kelly Rohrbach is perhaps best known as a Sports Illustrated model, so it was pretty inevitable she would catch DiCaprio’s eye.

They only dated for a few months in 2016, though, and split up when he was 41 and she was 25.

Nina Agdal: 25

DiCaprio’s pattern continues! Nina Agdal is another model, and she met DiCaprio in 2016.

They dated that year and broke up in 2017 but have remained friends since then.

At the time of the breakup, she was 25 (the magical number) and DiCaprio was 42.

Lorena Rae: 23

Did Leonardo DiCaprio actually date Lorena Rae? In typical Hollywood fashion, some think they were dating and others think they were just good friends hanging out.

Still, if they were dating in 2017 and broke up that year, she would have been 23 when they split and DiCaprio would have been 42.

Camila Morrone: 25

Camila Morrone was DiCaprio’s most recent long-term relationship.

They started dating in 2017, and it looked pretty serious when they began adopting dogs together.

Still, after four years together, they broke up in August 2022, two months after she turned 25.

DiCaprio was 47.

Fortunately for Leo, some new romance may be blooming on the horizon.

Maria Beregova: 22

According to The Sun, Leonard DiCaprio may have already found a new girlfriend. Her name is Maria Beregova, and she is a model (definitely DiCaprio’s type).

In July, the two were photographed partying together at a St. Tropez nightclub.

Still, the clock is ticking. Beregova is already 22 years old, so we hope she makes the most of this relationship while she can!

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