Stars by Day, Groupies by Night

Singer Ashlee Simpson's relationships have been in the spotlight as long as she has. Simpson has dated both high- and low-profile men. Her past relationships have included famous actors like Wilmer Valderrama and not-so-famous bandmate Braxton Olita. But Simpson seems to have finally found love with Fall Out Boy's Pete Wentz. Simpson and the rocker wed in May and are expecting a child together. Here, Simpson accompanies Wentz for a night out after a Fall Out Boy concert in Miami March 8, 2008. (Gustavo Caballero/Getty Images)