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.