10. Hugh Hefner & Crystal Carris. And now the break-up you've all been waiting for: Hugh Hefner and Crystal Harris. Some people thought the Playboy mogul would never settle down again, but all that seemed to change when the 84-year-old popped the question to 25-year-old Crystal at the end of 2010. The two were set to wed in June of 2011, but Crystal called it off just days before. To make matters worse, Crystal hosted a pool party at Wet Republic in Vegas the day she was set to wed. Tacky indeed. I'm just hoping Hugh and Holly Madison will make it work again. I liked them together.