Will Leonardo DiCaprio ever settle down?
While the Oscar winner has been in a serious relationship with girlfriend Camila Morrone for three years now, he's still known as one of Hollywood's most infamous bachelors. And he's got the dating resume, which holds zero public engagements, to prove it.
Since he first was spotted with one in the mid-'90s, Leo has shown quite the fondness for models. 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; in his long and lustrous 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.
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.