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Patrick Dempsey, 21

Patrick Dempsey, then 21, married his acting coach and manager Rocky Parker, then 47, in 1987. The couple divorced in 1994 and Patrick went on to marry his current wife, Jillian Fink, in July 1999. When talking about his May-October romance with Barbara Walters in 2006, Patrick joked that he "needed a mother."

Image Source: Getty / S. Granitz
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