Cradle-Robbing Celebrities

Hugh Hefner was engaged to 24-year-old Crystal Harris until she canceled the wedding. Now she says sex with the 85-year-old Playboy founder lasted "like two seconds." But Hef tweeted: "Crystal lied about our relationship." Hef had ended a relationship with 20-year-old twins to settle down with Harris, a December 2009 Playmate. Click to see more.
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Replay Slideshow

Cradle-Robbing Celebrities

It seems like a necessary stop on the path of a Hollywood starlet: move to LA, go on auditions and date a man your father's age. Here are a few of our favorite celebrity couples who think age ain't nothing but a number.

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