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George Clooney: His Lady Loves

Meet the women who were unable to tame Hollywood's most eligible bachelor – until now

KAREN 'DUFF' DUFFY

Dated in 1995
The former MTV VJ was Clooney's date to the 1995 Emmy Awards (pictured here). Although their relationship was short-lived, there seemed to be no hard feelings after it ended: Duffy set sail with Clooney and then-girlfriend Canalis on a Lake Como boat trip during the summer of 2010. "George, you know, he's very loyal," she told PEOPLE of their enduring friendship.