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...
The first model Leo reportedly romanced? Victoria's Secret model Bridget Hall, with the pair attending several events together in 1994. But her agent at the time denied any rumors that they were anything more than friends, saying, "I remember him. He was such a twitty little guy. They were friends, this is so so not true."
While Leo rarely walks the red carpet with any of his significant others, he was hand-in-hand with actress girlfriend Kristen Zang at the 1996 premiere of Romeo + Juliet. The couple dated for two years, before Kristen reportedly called it off in 1998. "She is the love of his life," a friend of Kristen's told The New York Daily News at the time. "She thinks he needs to grow up."
How serious were Leo and the world's most famous supermodel when they were together? Well, she is the only woman he's dated to ever accompany him to the Oscars.
The pair dated on and off for six years from 1999 through 2005, becoming one of Hollywood's hottest and most private couples. But in 2005, the Brazilian model made the decision to walk away. And then, in 2019, she finally opened up about the breakup to PORTER, revealing she was struggling with panic attacks and knew she needed to change her lifestyle.
"No longer numbing myself with smoking, drinking and too much work, I was becoming more and more aware of things that I'd chosen not to look at," she reflected in her book, Lessons: My Path to a Meaningful Life. "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes."
But in the end, it all worked out, as Gisele eventually married Tom Brady in 2009. Meanwhile Leo moved onto another serious relationship...
In 2006, he began romancing Sports Illustrated swimsuit model Bar Refaeli, who was 11 years his junior.
The pair split for six months in 2009, with Bar later telling L'Isha magazine she needed that time apart. "It was a half year for which I am very grateful," the Israeli supermodel explained. "I came to understand a lot of things about myself. "
"I worked on myself [and] I grew up," Refaeli continued "I didn't know what 'alone' was like. Today I know that a relationship can work only if you know you can be alone and you are not afraid. Today I'm not afraid of being alone."
By 2010, they were sparking engagement rumors, but a source shot down the reports to E! News. And by mid-2011, the couple split for good.
Spotted in May 2011: Hollywood's most in-demand actor and TV's It Girl getting cozy on a yacht in Cannes. Yes, before she married Ryan Reynolds, the Gossip Girl star dated Leo.
After first being seen together at the glam film festival (they reportedly met the previous November at a dinner for potential cast members for The Great Gatsby), Leo, then 36, and Blake, then 24, were photographed on dates and engaging in PDA in Italy, New York and Australia.
Alas, after just five months, the hottest couple of summer 2011 was dunzo, with a source telling E! News that the split was amicable.
Following his whirlwind romance with the Gossip Girl star, Leo began dating Victoria's Secret model Erin Heatherton in early 2012, with the pair being photographed zip-lining in Mexico with his mom, Irmelin.
However, they had amicably split by November.
Leo was first spotted with the Victoria's Secret model in 2013 when they were photographed kissing on a yacht in Ibiza. (Fun fact: This was the trip Leo infamously tried flyboarding.)
By 2014, the couple had enjoyed lavish vacations to Bora Bora, the French Alps and St. Barts. Plus, the German model attended a Golden Globes after-party with the star. In an interview with GQ, a then 22-year-old Toni looked forward to starting a family one day, though she didn't mention Leo: "I always wanted four kids. But we'll see. We'll start with one at some point, I don't know."
But after 18 months, it was confirmed the pair had split in December 2014. (Toni was noticeably absent from Leo's 40th birthday bash.)
However, the couple reportedly rekindled their romance briefly in 2017 when they were photographed together in NYC. As a source told E! at the time, "They are just hanging out and having fun. There's a history, so it's comfortable."
Next came the Victoria's Secret model and future Baywatch star in 2015, but after 18 months the pair had called it quits.
"This is a really busy time for both of them," a source said at the time. "They are both just so busy that it was hard to make a relationship work They are still very friendly. They really enjoy each other's company."
The Internet nearly shut down when photos of Leo and Rihanna getting very close at the 2016 Coachella Music Festival emerged, which came just a year after the two reportedly were kissing at a Playboy Mansion Party.
So when they were spotted together once again at the Neon Carnival, the rumor mill ran rampant. But a source denied the pair were an item. "They are friends and still hang out," an insider shared. "They both like the same type of music and that's usually when they run into each other. Neither of them are looking for any type of relationship now."
While Leo was first linked to the Danish model as early as 2014 when they were spotted at the same Super Bowl party, Nina shot down the romance rumors. "I've never met him, but I have a friend who got invited to dinner with him," she told Cosmo. "But, you know, whatever. It's kind of the group you interact with, people that you meet at parties, so that would be only natural."
Noting that he "likes blondes," the Sport's Illustrated star admitted they had crossed paths a few times before. "If you're in New York City, you always see him around."
But by May 2016, Nina and Leo were an item, with a source saying, "They have great chemistry and laugh a lot." Alas, after a year together, including vacations to the Bahamas and Montauk, E! News confirmed their romance had ended in May 2017.
"They remain in touch and remain friends," a source close to the former couple revealed at the time. "It's an amicable split, and they're moving forward."
In May 2017, Leo and the model sparked romance rumors when they were spotted together at the amfAR charity gala during the Cannes Film Festival, just after news of his split from Nina broke.
But a source at the time confirmed both the actor and Bella were single and there was nothing going on. "Leo is not looking for another girlfriend," a source explained. "He is just doing Leo. Leo is a flirt, always has been."
But it turns out Leo was actually ready to get a bit more serious, as he started dating girlfriend Camila Morrone in April 2018, with the duo first spotted engaging in PDA at Coachella (though they were first photographed together in December 2017).
While Leo's romance with the then 21-year-old actress started off "relaxed," a source told E! News in November of that year that it was "getting more serious. They've been inseparable for the last year and are crazy about one another. They've gotten to know each other's families and they love being together."
Unlike some of Leo's previous girlfriends, Camila hasn't been afraid to casually address their relationship, even clapping back at hateful comments after she posted an Instagram of the late Lauren Bacall and Humphrey Bogart. "A love like this," she wrote alongside the pictures of the couple, who had a 20-year age difference between them.
When fans came after her, she was quick to respond on her Instagram Story. "I just read some of the comments on my Instagram and...my God, people are so mean and full of anger with people that they know nothing about."
Since then, she's supported him at events promoting Once Upon a Time...in Hollywood, with Leo returning the favor, playing Instagram Boyfriend for her during their time at Cannes. "I saw the meme," Camila later told Vanity Fair. "Poor thing, he's being called an Instagram boyfriend. He's an environmentalist and a movie star and it doesn't mean a thing!"
But just two months after the actress' 25th birthday, the pair called it quits, sources close to the couple confirmed to E! News in August.
"Distance played a factor," a source said, adding that the romance "ran its course."
This story was originally published on Monday, Nov. 11, 2019 at 10 a.m. PT.