It can't be easy for one tiny blond billionaire to find a decent guy, let alone two — but somehow, Mary-Kate and Ashley Olsen [1] have managed to amass some pretty high-profile partners (as well as a small fortune) over the years. We can deduce a few things from the former actresses and current fashion industry heavyweights' [2] combined dating history: they often pair up with men whose net worth can match their own, as well as those who are older (read: wiser) than they are and, in some cases, have dated other female celebrities. From trust-fund babies and Hollywood bad boys to artists and CEOs, here are 20 men who have romanced the Olsen twins.

Jared Leto

Jared and Ashley seemed to have had an on-off friends with benefits sort of thing over the years; they were first linked in 2005 after being spotted on a date in LA but came back together in 2008 when they were seen holding hands and "making out" at the Art of Elysium Gala [3] in LA. An eyewitness told Us Weekly at the time that they "looked like a couple," but a source close to Ashley insisted they were just friends. Cut to 2011, and the "friends" were reportedly seen enjoying a "very flirtatious meal" at the Polo Lounge [4] in Beverly Hills.

George Condo

Ashley was linked to the renowned artist in Summer 2016 [5] when she was 30 and he was 59; the two were seen lunching in a "cosy" booth in NYC. Ashley and George, who split from his wife of 26 years a year earlier, had previously worked together on her fashion house The Row and created a sketch of the brand's NYC boutique [6]. Their relationship fizzled out a couple months later.