Leonardo DiCaprio started dating hot 25-year-olds back in the roaring ’90s and…truly nothing has changed! Other than the people he’s dating, of course, because lord knows this man won’t stay with someone once they show any signs of aging. On that note, we’re taking a look back at Leonardo DiCaprio’s dating history, which is almost as long as the wrinkle on my forehead that would probably horrify him.

Leo and Bridget were linked very early in his career, although she told New York magazine that “nothing happened” in 1998, denying previous claims that she’d once said, “He was lousy in bed. The sex was bad.”

1995: Naomi Campbell

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Like most of the model romances he had in the roaring ’90s, Naomi and Leo’s relationship was both very rumored and very brief. Unlike most of the models he dated in the roaring ’90s, they’ve stayed close friends over the years!

1996—1997: Kristen Zang

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Kristen actually spoke out about her relationship with Leo to People last year, saying, “It was a different time back then. We could go places and not be followed by the paparazzi. It was 1995 and he was making a movie called Marvin’s Room. I remember vividly while visiting him on the set, watching the O.J. Simpson verdict while in Meryl Streep’s trailer. It was a surreal moment for a Michigan country bumpkin like myself.”

She added, “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. 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.”

FYI, she’s the one who ended it!

1997: Amber Valletta

A story in three parts: Leo saw Amber in a magazine, he was smitten, and they briefly dated. But the two never confirmed it themselves, FYI.

1997: Helena Christensen

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Helena and Leo were linked together in the ’90s, but again…no actual evidence that they dated due to the internet not being a big thing yet. Tabloids could only do so much, ya know?

1998: Eva Herzigová

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These two met at the premiere of The Man in the Iron Mask (lol), and according to The Mirror Eva mused, “He’s a wonderful person. Our first night was a really nice experience. He is a very kind person and full of energy.”

2000: Virginie LeDoyen

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Leo and his The Beach costar were rumored to be dating during filming, but that may have just been tabloid speculation. Especially since Virginie had this to say to The Guardian about that time in her life: “The whole thing was really aggressive. I guess I was very, but the violence of the attention took my breath away. I tried to laugh it off, because if you don’t laugh, you start crying. And then you’ll never stop.” She added, “DiCaprio’s life is the perfect example of how not to be. I would not wish his life on anybody. I can understand how it might seem a bit flattering to be in every newspaper and to have everyone imagining how your life must be. But frankly it’s not.”

2000—2005: Gisele Bündchen

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These two dated for five entire years! Their respective ages at the time of their split? Leo was 30, Gisele was…you guessed it! 25. She wrote about their breakup in her book, saying, “No longer numbing myself with smoking, drinking and too much work, I was becoming more and more aware of things that I’d chosen not to look at. Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes.”