Mary-Kate Olsen Had Quite a Few Boyfriends Before Settling Down With Ex Olivier Sarkozy

Her most famous relationship may be with estranged husband Olivier Sarkozy, but Mary-Kate Olsen’s dating history includes plenty of stars. From shipping heir Stavros Niarchos III to Heath Ledger, she’s been linked to celebrities both inside and outside of Hollywood. And though she may have a reputation for getting into relationships with older men, it was actually twin sister Ashley Olsen who started that trend.

Mary-Kate, 33, may have ended up settling down with a man 17 years her senior, but most of her boyfriends were just a few years older. Her first boyfriend was Max Winkler, Henry Winkler’s son. Though he’s three years older, they grew up in the same L.A. private school circles. “I dated an Olsen twin because I was in love with an Olsen twin,” Max, 36, said in a 2011 interview with New York Magazine. “But I wasn’t in love with her because she was ‘an Olsen twin.’ I just thought she was so pretty and smart and cute.”

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After their breakup, she went on to date DreamWorks cofounder Jeffrey Katzenberg’s son, David Katzenberg, who was also only three years older. The couple dated for a year despite the fact that the TV producer was currently attending college across the country at Boston University. When she found herself starting to pursue her degree at New York University, they decided to go their separate ways and parted on friendly terms.

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It was only once the Olsens were 18 and Ashley, now 33, was dating someone 12 years her senior that her sister finally started following in her footsteps. While Ashley dated nightclub owner Scott Sartiano, her twin was linked to his business owner, Ali Fatourechi. However, the Genetic Denim founder and actress had a (slightly) more reasonable age difference of only 8 years. Ali, now 42, was only 26 at the time.

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As Mary-Kate got older, the age differences in her relationships continued to grow, but her largest yet is with ex Olivier, 50, and the May-December aspect of their relationship didn’t seem to have an impact on their love. After walking down the aisle in November 2015, the New York Minute star happily stepped into the role of wife and step-mother to the French banker’s two teenage children, Margot and Julien.

Now, the couple is splitting in what seems to be a contentious divorce — but, luckily, there’s one relationship MK will always be able to count on, and that’s her unbreakable bond with Ashley. Check out the gallery below to see Mary-Kate Olsen’s full dating history.