10. George Clooney and Sarah Larson

Mario Anzuoni / Reuters
It was beginning to look like this perpetual bachelor had finally found his match. Clooney, 47, met Larson, 29, a cocktail waitress and former Fear Factor winner, in Las Vegas. The two started dating in 2007, stepping out at the Venice and Deauville film festivals. In September of last year they suffered through a motorcycle accident together and earlier this year, she became the first girlfriend ever to go with Clooney to the Oscars. But by March, he was deflecting rumors of an engagement, and by May the twosome went their separate ways. And the prayers of delusional women everywhere were answered.

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