Leonardo DiCaprio’s Complete Dating History

Leo’s a great actor, you can’t deny that. But his dating history has been so extensive and kind of predictable that it basically became a meme. Now we all jokingly predict the demise of each of his relationships the moment his model girlfriend turns 25. But has it really always been that way? Were there any exceptions? Is there any sign of change now that he’s gotten older?

1994: Bridget Hall

Leo’s first major rumored romance was with model Bridget Hall. At the time, he was fresh off What’s Eating Gilbert Grape and just entering the public eye. The New York press hinted that the two hooked up, but by 1998 Hall denied it ever happened, even claiming, “nothing happened.” Tabloids had painted it as a fling gone wrong, but Hall later brushed it off as overblown speculation.

1995: Naomi Campbell

The following year, Leo was linked to Naomi Campbell — and who wasn’t in the ’90s? Their romance was reportedly brief, more of a spark than a full-on relationship, but the two remained close friends. Unlike many of his exes, Naomi kept him in her inner circle, and the pair have been spotted together socially years after the fact.

1996–1997: Kristen Zang

Kristen Zang was one of Leo’s first serious girlfriends. She even spoke candidly to People about their romance, describing him as thoughtful and sweet. They traveled together while he filmed abroad, hung out with each other’s friends, and lived something close to a normal relationship despite the fame. Kristen ended things a few months after her 25th birthday — not that she didn’t notice the timing herself, joking about the “25 rule” in hindsight.

1997: Amber Valletta

Amber Valletta was another one of Leo’s supermodel crushes. The story goes that Leo spotted her in a magazine, asked someone to track her down, and they briefly dated. Neither of them confirmed the romance publicly, but the story has lived on as a classic Leo move.

1997: Helena Christensen

That same year, Leo was also linked to Danish model Helena Christensen. Like Amber, their supposed relationship was more rumor than fact, fueled by the limited tabloid culture of the late ’90s. With little evidence to back it up, this one goes down in history as more speculation than romance.

1998: Eva Herzigová

These two met at the premiere of The Man in the Iron Mask and apparently the connection was almost instant. Eva publicly spoke about DiCaproio,  said Leo was a kind man, full of energy, and no to subtly hinted at a memorable first night together. It didn’t last long, but Eva’s rare public comments made this fling more than just a whisper.

2000: Virginie LeDoyen

Leo was linked to his French co-star Virginie LeDoyen since they worked together on The Beach,. Rumor has it that their on-screen chemistry carried over off set, but LeDoyen later dismissed it as tabloid exaggeration. She was far more focused on criticizing the overwhelming media frenzy and said she would “not wish” his level of fame on anyone.