Couple Nickname: None
Dated Between: 2010 - 2011, 2012 - Present

The first time 86-year-old Hugh Hefner and 26-year-old Crystal Harris got engaged, we were pretty confused. The eternal bachelor and symbol of the ultimate player, settling down?! But if he was happy, that's all that matters. Then, when Crystal Harris ran off five days before their wedding and they called the whole thing off, we figured it was for the best. If Hef was going to get married to anyone, it should be to someone who actually respects him.

A few months later, though, the two suddenly got engaged yet again, seemingly out of nowhere. They were married on New Year's Eve, and as per their iron clad pre-nup, if Hef dies or they divorce, Crystal is to vacate the mansion and she has no stake in his estate. We can't help but think that this isn't going to end well.