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Hugh Hefner

And when Hefner "cleaned house," he was left with these three ladies: Holly Madison, Bridget Marquardt, and Kendra Wilkinson. Each woman caught his eye at various times, but they came together in 2005 for a reality series about life at the mansion called “The Girls Next Door.” For six seasons they shared their lives behind the walls at the mansion, but Hefner's relationship with each woman started to unravel. First, Wilkinson fell in love with NFL player Hank Baskett, who she went on to marry; Madison, his No. 1 girlfriend, dumped Hefner when he told her he didn’t want to get married again or any have more children (she's currently pregnant); and Marquardt was the last to leave, in 2009, because she wanted to become her own person. Although the romance fizzled, Hef has remained on (mostly) friendly terms with all three women.

Hugh Hefner's Many Exes

Playboy mogul Hugh Hefner finally tied the knot with on-again, off-again girlfriend Crystal Harris on December 31, 2012. But she wasn't the first girl to win his heart. Take a

trip down memory lane with omg! as we look back at some of Hef's

gal pals from over the years.