Wilmer Valderrama

Noted player Wilmer Valderrama hasn't had a serious relationship in years, but his past is rife with young starlets and singers. He dated singer Mandy Moore from 2000 to 2002, and then moved on to actress/singer Lindsey Lohan, a relationship that lasted from 2003 to 2004. Aside from these few, long-term relationships, Valderrama has been linked to singer Christina Milian, actress/singer Jennifer Love Hewitt, actress Mischa Barton and singer Ashlee Simpson. In 2006, Valderrama made headlines by dishing on his past relationships on the Howard Stern show, even going so far as to discuss penis size, his taking of Moore's virginity, and the sexual ability of his other girlfriends. His exes were not amused. Most recently, he's been seen chatting up singer Rihanna over a glass of Champagne, and also getting cozy with the newly-divorced Avril Lavigne.