Celebrity Couples What It's Like To Date Leonardo DiCaprio  

Greg Benevent
18k views 12 items

Hollywood bachelor Leonardo DiCaprio has dated and broken up with some of the most beautiful women in the world. DiCaprio, with acting chops, Hollywood looks, and lots of famous friends, has been on the relationship market for some time, and stories about dating him are varied and legendary. But even though he's done some really 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 (with at least one exception), jet-setting to exotic locations, partying at Paris nightclubs, and 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 happened in 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 glean a few things about what's it's like to date Leonardo DiCaprio. 

Cara Delevingne Allegedly Said... is listed (or ranked) 1 on the list What It's Like To Date Leonardo DiCaprio
Photo:  Gage Skidmore/Wikimedia Commons/CC BY-SA 2.0

Cara Delevingne Allegedly Said Leo Was 'Too Forward And Too Old'

DiCaprio's super-stardom does not make him immune to dating rejection. If you listen to the rumor mill, it apparently has happened to him at least once. Famous model and actor Cara Delevingne allegedly wanted nothing to do with him when he approached her at a party in 2013, saying he was "too forward and too old."

Some reports even say he "[begged] her to go back to his hotel room." 

Blake Lively Sent Him Pictures... is listed (or ranked) 2 on the list What It's Like To Date Leonardo DiCaprio
Photo:  Century Black/Flickr/Public Domain

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. According to Gossip Girl producer Joshua Safran, Lively sent DiCaprio pictures of a "Flat Stanley-style doll."

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 Wo... is listed (or ranked) 3 on the list What It's Like To Date Leonardo DiCaprio
Photo: Jesse Grant/Stringer/Getty Images Entertainment

Rihanna Reportedly Hoped He Would Commit

In March 2015, when asked if she was dating DiCaprio, singer Rihanna said: "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... is listed (or ranked) 4 on the list What It's Like To Date Leonardo DiCaprio
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.