It’s no secret dashing actor Leonardo DiCaprio is a bit of a ladies man. Well, he’s actually the ultimate ladies man. From a very long list of models to supposedly hitting it up with Rihanna, here are the 25 hottest celebrities Leo has been linked to over the years.
Leo and Juliette were rumored to have been an item after meeting during the filming of What’s Eating Gilbert Grape
Blake Lively 2011
The two dated for about a summer. How could you possibly give up Blake Lively?!
The Romanian actress and model was rumored to be with Leo in 2011
The two starred in Romeo and Juliet together, and may have had a real-life romance outside the film.
Even though the two claim they have always just been friends, there was some gossip about the two of them dating.
Rihanna and Leo were in the tabloids after they were rumored to have hung out at the Playboy mansion together.
This babe is Leo’s official girlfriend as of right now. Nice work dude.
A Playboy cover model, Phillips was rumored to be dating Leo in the late ‘90s.
Leo allegedly spotted the actress in a magazine and had his agent arrange a meeting.
The two had been on-and-off for quite some time.
How’d you let this beauty get away, Leo?
Another rumor but she’s so gorgeous we’d believe it.
We’d say landing a Sports Illustrated Swimsuit model was a definite win for Leo.
No one really knows if they actually were together, but it wouldn’t be associated with blonde bombshell Sienna Miller
Russian and a model? Nice land, Leo.
And another model…
And THE hottest super model in the entire world. Because of course he would date her.
This was Leo’s apparent love interest in 2011. Yes, she’s a model.
The two were never confirmed to be dating but they hung out quite a bit. It was rumored Leo took Hall’s v-card. Guess we’ll never know.
The Victoria’s Secret angel dating the actor for almost a year.
You guessed it: Another model, this time a Hungarian one.
Toni Garrn 2013-2014
The German model is known for her work with Calvin Klein, and dating the Wolf of Wall Street star for about a year
Alicia Silverstone 1997
The two are rumored to have dated during Silverstone’s big break in Clueless.
Kristen Zang 1996-1997
The actress was linked to Leo during the mid-90s after his giant success in Titanic.
Alyce Crawford 2011
Apparently Leo started dating the Australian model just days after splitting from our girl Blake Lively in 2011. Tough love.