Has Leonardo DiCaprio Ever Dated Anyone Over 25 Years Old?

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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?