The Many Loves Of Hugh Hefner, The Luckiest Bastard In The World

The Shannon Twins
Karissa and Kristina Shannon quickly moved it after the original Girls moved out, though we doubt Hef's eyesight is good enough to really tell the difference between any of them. We like to imagine that Hugh thought he was only dating one girl, and the twins would constantly be switching which one was with him, like a very raunchy episode of Sister, Sister. Hugh eventually dumped the girls for being unfaithful, most likely with men their own age. That is to say, high school seniors. So just to recap, Hugh Hefner dumped his twin teenage girlfriends not because they were young enough to be his grandchildren, but they offended his moral sensibilities. [Photo: Splash News Online]