Will Leonardo DiCaprio ever settle down?
It seems like that question is still unknown. After four years of dating, the Oscar winner and actress girlfriend Camila Morrone have broken up, putting one of Hollywood's most infamous bachelor back on the market.
Wary of that title? Well, he's got the dating resume, which holds zero public engagements, to prove it.
Since he first was spotted with a model in the mid-'90s, Leo has shown quite the fondness for catwalkers. Hey, everyone has a type, right! But do you remember that that five-month romance with Blake Lively that had everyone gossiping?
And one thing's for sure: A relationship with the Once Upon a Time...in Hollywood star is an adventurous one, filled with lavish vacations, trips to the Cannes Film Festival and lots of bike rides in NYC. Plus, you might just find yourself becoming a viral meme.
Still, Leo doesn't get serious with just anyone. Throughout his career, Leo has walked a major red carpet, hand-in-hand with just two girlfriends—and only a handful of women have met his mother. (While he and Camila attended the 2020 Oscars together, they posed on the carpet separately.)
So let's take a stroll down memory lane and look back on Leo's stacked dating history...
This story was originally published on Monday, Nov. 11, 2019 at 10 a.m. PT.