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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 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' 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.

Ashley
Matt Kaplan
Scott Sartiano
Jared Leto
Greg Chait
Lance Armstrong
Justin Bartha
David Schulte
Bennett Miller
George Condo
Richard Sachs
Mary-Kate
Max Winkler
David Katzenberg
Ali Fatourechi
Stavros Niarchos
Max Snow
Heath Ledger
Lapo Elkann
Nate Lowman
Dustin Yellin
Olivier Sarkozy
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