Celebrity divorce smackdown

The would-be Hefners: Hugh and Holly

“Girl Next Door” Holly Madison never did manage to walk down the aisle with Hef, perhaps due in no small part to the fact that he remains married to (though separated from) his second wife (who, ironically, actually lives next door to the Playboy Mansion with their two sons.) Although the seven year relationship never yielded the children or wedding Madison wanted, she did score three Playboy covers and a reality show, and Hef has allegedly moved on to teenage identical twin girlfriends. Breaking up isn’t always that hard to do.

Better off? Holly. She may be out of the Playboy Mansion and have to find a job, but at least she doesn’t have to share her bed with a man that could be her grandpa’s grandpa (love ya, Hef!).