What It's Like To Date Leonardo DiCaprio

Hollywood bachelor Leonardo DiCaprio has dated and broken up with some of the most beautiful women in the world. With acting chops, Hollywood looks, and lots of famous friends, he has been on the relationship market for some time, and stories about dating Leonardo DiCaprio are varied and legendary. But even though he's done some cool things, not all of DiCaprio's exes have nice things to say about the actor.

If you've ever pined after DiCaprio (or his famed Titanic persona, Jack Dawson), you may have wondered what it would be like to date him. Sure, his love interests have enjoyed walking down red carpets, jet-setting to exotic locations, partying at Paris nightclubs, or lounging around Hollywood mansions, but what are the downsides of dating one of the world's most famous movie stars?

A lot of what's known about DiCaprio's relationships is based on rumors or comments from anonymous sources - apparently, his exes don't do a lot of kissing and telling - but we can still glean a few things about what's it's like to date Leonardo DiCaprio. 

  • Blake Lively Sent Him Pictures Of A Doll
    Photo: Andrea Raffin / Shutterstock.com

    Blake Lively Sent Him Pictures Of A Doll

    For a few months in 2011, Leo dated Gossip Girl star Blake Lively. Today, Lively posts tons of photos on Instagram chronicling her relationship with husband Ryan Reynolds. Back in her DiCaprio days, though, Lively had a different photo-sharing routine. As Gossip Girl producer Joshua Safran told Vanity Fair, Lively sent DiCaprio pictures of a doll as a way of documenting her life.

    Instagram was around at the time, but not as widely used as it is now. As Safran said, Lively "was documenting her life in photographs in a way that people were not yet doing." 

  • Rihanna Reportedly Hoped He Would Commit
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    Rihanna Reportedly Hoped He Would Commit

    In March 2015, when asked if she was dating DiCaprio, singer Rihanna told Hello! magazine: "It sounds to me like you should stay away from the blogs because they will screw you every time." But a month later, according to In Touch Weekly's sources, the couple would "hook up and go to each other's houses every night." The sources said Rihanna had originally ended their relationship because he wouldn't commit, but was holding out hope.

    In 2016, they were seen kissing at a Paris nightclub, but apparently, it was just a friendly kiss on the cheek.

  • Gisele Bündchen Said They Were 'Just Not Meant To Be'
    Photo: Featureflash Photo Agency / Shutterstock.com

    Gisele Bündchen Said They Were 'Just Not Meant To Be'

    Before she married Tom Brady, model Gisele Bündchen dated DiCaprio. Apparently, their break-up was amicable, and she has said many positive things about him. In 2009, she told Vanity Fair:

    Leo is a really wonderful person... We still speak sometimes, and I'm friends with his mom. He still has one of my dogs. He’s done a lot for the environment, and I admire what he’s done. We know what we had; we were very young, and we grew together in a lot of ways. We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best.

  • Bar Refaeli Didn't Want To Be On The Red Carpet With Leo
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    Bar Refaeli Didn't Want To Be On The Red Carpet With Leo

    For years, Leo and Israeli model Bar Refaeli had an on-again, off-again relationship. During their relationship, she was supportive but didn't want to be prominent on the red carpet at his events. According to People, she told the Israeli magazine La'Isha:

    I just don't walk hand-in-hand with him. I don't see any reason. I don't need to strike a pose with him in front of the cameras... no one needs to know how we kiss. 

  • Nina Agdal Realized Leo Wasn't Ready To Settle Down
    Photo: Sky Cinema / Shutterstock.com

    Nina Agdal Realized Leo Wasn't Ready To Settle Down

    DiCaprio dated model Nina Agdal for roughly a year in 2016 and 2017. Longtime Leo watchers will note it was one of his more extended relationships. When the duo broke up, a source close to DiCaprio told People the reason for the split: "He's not ready to settle down and just isn't in the mindset to get married or have kids."

    That doesn't mean their breakup was acrimonious, the source said. DiCaprio considered Agdal a "super cool girl," but his friends "knew it wouldn't last." Why not? According to the source:

    It will happen one day, but it will really take someone special to make him go the distance. He loves all the attention he gets from women. 

  • Leo Broke Up With Kelly Rohrbach Around The Time Of His Oscar Campaign
    Photo: Jean Catuffe/Contributor / GC Images/Getty Images

    Leo Broke Up With Kelly Rohrbach Around The Time Of His Oscar Campaign

    For years, "Leo doesn't have an Oscar" was like "the Buffalo Bills haven't won a Super Bowl." In early 2016, DiCaprio, then an Oscar contender for The Revenant, broke up with girlfriend Kelly Rohrbach. Conspiracy-minded relationship watchers noted that around this time, Rohrbach was cast to play the Pam Anderson role in the Baywatch movie. They suggested DiCaprio might not have wanted to associate himself with anything other than high-brow cinema.

    While it's possible the breakup was influenced by DiCaprio wanting to help his Oscar chances, a source told Us the mutual split happened because of their "intense work schedules," and they had "a lot going on in their lives."