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George Clooney, Talia Balsam
In 1989, following his split from Preston, Clooney tied the knot with "Mad Men" actress Talia Balsam -- who was two years older than him! Four years later, the couple divorced, which left Clooney with a fear of marriage. But not Balsam. In 1998, she said "I do" to another gray-haired hunk: John Slattery, who plays her TV husband on "Mad Men."

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