Crystal Harris

Crystal Harris looked the part of any of Hugh Hefner's girlfriends-blonde, busty and "perfect," but behind that pretty smile was a sinister plot to make money off of the misfortune of Hugh Hefner. Once Crystal was set to marry the Playboy head honcho she pulled out at the last minute, saying that she just couldn't go through with the marriage. However, she was busted trying to secretly secure a $500,000 media deal for her story.

In the end Crystal didn't get the deal she wanted, but Hugh let her keep the engagement ring and the Bentley he bought her. They've since reconciled and are now back together.