Yep, we all know that Mary-Kate and Ashley Olsen‘s dating history is full of way older guys. In fact, some of them are so much older that their romantic dates look more like a dad taking his daughter out for her birthday. But the reality is, it wasn’t always like that. Back in the day, the Olsen twins were normal teenage girls (okay, you can only be so normal when you’ve got your own media empire as a child) dating normal teenage boys. But somewhere along the way, things got out of hand — and the girls started dating up. Want to know all the guys they’ve been linked to over the years? Watch the video below to see their dating history — and all the enormous age gaps.

Back in high school, they were both dating guys who were (basically) age-appropriate. Ashley dated Matt Kaplan, Claire Holt‘s now ex-husband, and Ashley dated Henry Winkler‘s son, Max, and TV producer David Katzenberg. The guys were all three years older, which was maybe a little scandalous since the twins were in school and the guys were in college, but it was still pretty normal. So what happened after that? Though MK is better known for her famously older husband, it seems like it was actually Ashley who started the trend. MK may be the fashionista of the fam, but when it comes to dating up, her sister is the queen.

mary-kate olsen dating history

Yep, Ash snagged a 30-year-old boyfriend (aka a full 12 years older than her) when she was still just 18. And then she roped her sister into dating his business partner, who was 26, presumably so that she wouldn’t have to wait alone while their boyfriends ran a nightclub they were not legally allowed into. Again, not totally scandalous for Hollywood, but like, pretty insane for two baby-faced, 5’1″ child stars. MK managed to break the cycle — at least until she was more firmly into her 20s — but for Ash, that was just the start of a line graph that seemed to chart higher and higher with each boyfriend’s age. She even tangled with Johnny Depp, a full 23 years older.

Weirder still, while she was dating director Bennett Miller, 20 years her senior, the couple went on a date with MK and her 17-years-older boyfriend. (Side note: Can you imagine being Olivier, invited to double date with the Olsens, and finding out the other guy is actually even older than you? Think they set up an adults table and a kids’ table?) The oldest Ash dated was her most recent boyfriend, who she broke up with about a year ago when she was 30 — and he was 64. Dang.

ashley olsen boyfriend

So why do the Olsen twins do this, when they are still, for the most part, young and cute (when they try) and also total catches considering they’re worth about a bajillion dollars each? Well, maybe that bajillion dollar net worth is part of it. Between the two of them, they’ve dated TV producers, the already successful president of their own fashion line, fellow megastars, restaurateurs, art dealers, billionaires, and the brothers of presidents. Aka, other than in their teen years, no normies. It’s no stretch to imagine that, being the head of their own movie company and fashion lines, they’d want to find equally accomplished partners. And yeah, we can see that might mean dating older guys. But personally, we’re just going to imagine that, after growing up in John Stamos‘s arms, he’s just their dream man and so now they’re constantly chasing guys with at least 20 years on them.

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