Photo: Jay Valena/John Spellman/Bill Davila/Byron Purvis/AdMedia/Retna Ltd.
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Dating type: The (almost) jailbait
By the time Wilmer Valderrama told Howard Stern that he took Mandy Moore's virginity, he moved from suave bola to all-out sleaze. The Latin ladies' man frequently chose the barely legal (Moore and Lindsay Lohan were 17; Demi Lovato was 19) to decorate his ride, his crib and his side.