Charlie Sheen and Ginger Lynn (2/15)

There are many celebrities who have dated adult stars, but not many that have dated five of them. Movie and TV star Charlie Sheen has been with porn stars Capri Anderson, Bree Olson, Ginger Lynn, Melanie Rios, and his current fiancée Brett Rossi. His relationship with Ginger Lynn was among the longest, and lasted five years, from 1990 to 1995. They met on the set of Young Guns II, in which Charlie’s brother Emilio Estevez starred. Charlie gives her credit for inspiring him to pursue sobriety when he was struggling with addiction to drugs and alcohol and giving the strength and support he needed to be successful. They remain friends to this day. However, Ginger Lynn warned Charlie Sheen’s fourth fiancée, twenty-four-year-old Brett Rossi, “This won’t be his last marriage.” Which is a very reasonable warning to give a man’s fourth fiancée.