As you might expect from an Academy Award-winning actor, Sean Penn's dating history is primarily made up of fellow A-list celebrities. However, much like his "Battle of Baktan Cross" co-star ...

64-year-old Sean Penn sparked heated debates on social media after making a red-carpet debut with his girlfriend, 30-year-old Valeria Nicov.The couple attended the 21st Marrakech International ...

Taylor Hill/FilmMagic; Stephane Cardinale - Corbis/Corbis via Getty Madonna and Sean Penn’s marriage ... adds of when the pair started dating. “America’s bad boy and America's bad girl.” Madonna, now ...