Crystal Harris
Playboy founder Hugh Hefner has long been known for his hordes of Barbie-like girlfriends. In recent years we've seen them showcased on his reality-TV show The Girls Next Door, in which he lets cameras into his home and relationships. He hasn't, however, been so well known for his marriages, though he's had a couple of those over the years as well. So when the 85-year-old Hef announced his engagement to his girlfriend, 25-year-old Playmate Crystal Harris, it was big news. Not only was Harris about to marry the most famous playboy in the world, but she would also be doing so shortly after Hef broke the likable Holly Madison's heart. But the marriage was not to be. On June 14 — less than a week before the big day — Harris called the wedding off, later blaming the breakup on the couple's inadequate sex life. The split didn't help Harris' celebrity status: her burgeoning singing career fizzled, and obviously, she lost her spot on his show.