5. The Hugh Hefner-Crystal Harris Engagement. Anybody else remember that really uncomfortable episode of Holly's World where Holly Madison finds out Hugh Hefner is engaged to girlfriend Crystal Harris? Well, looks like Holly didn't need to be that upset because the marriage didn't even happen! After getting engaged at the end of 2010, Hugh and Crystal were happy. Everything seemed fine till out of the blue the two called off their engagement. Oddly enough, Crystal didn't seem to care. The little miss thought it would be a good idea to host a pool party at Wet Republic the day she was set to say "I do." Umm, no. Even Holly had something say in the matter. Maybe now Holly and Hugh can get back together! Yay!