18. Charlie Sheen
Photo: independant
When he’s not “winning,” or drinking “tigers blood,” the maniac we all know and love, Charlie Sheen, has spent his fair share of time on dating websites. While he might be a prime candidate for Tinder, Sheen’s actually a member of the exclusive site, MillionaireMatch.com. Presumably, it’s a site that specializes in gold diggers that are looking for a certain lifestyle that only a millionaire could provide. With the exception of short term hookups, Sheen hasn’t had the best of luck when it comes to the females in his life. He apparently has high hopes for this MillionaireMatch.com though. Only time will tell.