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Despite being one of Hollywood’s biggest playboys, not much is known about what it’s like dating Leonardo DiCaprio. We can imagine it’s full of glitz, glamour, and a whole lot of star-studded yacht trips; but what about the dynamic? We know he likes dating women half his age, and by his past track record, he likes to date them up until they’re 25 so we know there’s a huge age gap — but what else?
There’s been a long-standing rumor that the Wolf of Wall Street star makes his partners sign a non-disclosure agreement, or NDA, to keep details out of the press. However, that’s never been confirmed or denied to this day.
But even if there were an NDA present, it’d be a more recent development, because some of his girlfriends from the 1990s and early 2000s have spilled the tea here and there throughout the years.
While some have talked about the real reason why they called it quits, others have talked about their relationship when they were together. And one of his exes gave so many details about both. (Any guesses? Here’s a hint: she was in one of his longest relationships ever.)
DiCaprio has dated quite a few A-listers over the years, but only four have come out and said anything about the relationship (and one reportedly had some harsh things to say about his bedroom skills).
Check out which of DiCaprio’s exes have spoken up about their relationship details, why they broke up, and more, below:
Bridget Hall
While many claimed “nothing happened” that caused Bridget Hall and Leonardo DiCaprio’s breakup, many other outlets reported that she said, “He was lousy in bed. [It] was bad.” Ouch. The pair dated for a month in 1994.
Kristen Zang
Leonardo DiCaprio’s ex Kristen Zang has been one of his most loyal supporters over the years, from writing essays and clapping back at people making fun of him dating women half his age. Back in 2022, she spoke out about their brief relationship from 1996 to 1997 to People.
“I visited Leo for long periods of time on various sets in different countries. I loved his friends and he loved mine. We were like one big happy family. Leo was a very sweet and thoughtful boyfriend,” she said. “We also had some hard times like all couples do, and broke up for a bit in 1997 and then got back together. Then, about 4 months after my 25th birthday (ha, I know what you’re thinking) it was over for good.”
Gisele Bundchen
One of Leonardo DiCaprio’s longest relationships was with Gisele Bundchen, whom he dated from 2001 to 2005. Bundchen has spoken about their relationship the most out of all of his exes.
In a 2009 interview with Vanity Fair, she spoke about it, and had quite nice things to say. “Leo is a really wonderful person,” she said. “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.”
However, she spoke more candidly about the relationship again in her 2018 memoir entitled Lessons: My Path To A Meaningful Life. Not only did Bundchen say she was the one who broke off the relationship, but she didn’t want to numb herself with distractions like, “smoking, drinking, and too much work, I was becoming more and more aware of things that I’d chosen not to look at.”
She added that she did some “serious soul-searching while he stayed the same.”
Erin Heatherton
From 2011 to 2012, Erin Heatherton and Leonardo DiCaprio were in a very private relationship and eventually broke up due to their crazy schedules. While they’ve never spoken about the details of their relationship, E! News talked to her soon after her breakup, and she seemed to be doing better than ever afterward. She said, “I’m having the best time right now. I couldn’t feel more beautiful with all my friends. It’s wonderful.”
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