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George Clooney is Hollywood's posterboy for perennial bachelorhood. After divorcing from actress Talia Balsam back in 1993, Clooney's adopted a very strict "no marriage" policy, and his string of flings over the course of the last two decades has done nothing to suggest his stance will change. From co-stars to models to waitresses to WWE wrestlers to Oscar winners, Clooney's dating history is one for the ages. (There's even some overlap, because of course.)