Hugh Hefner

Hugh Hefner married Mildred Williams in 1949, but the couple divorced in 1959. They had two children Christie and David. Hef has had relations with many of his playmates, but did not remarry again until 1989 when he married Kimberly Conrad. They had two sons Marston and Cooper, but separated in 1999. He and Conrad remained legally married until 2010. Thoughout their childhoods, Kimberly and her children lived in their own house next door to the Playboy Mansion while Hef continued to date a string of young playmates, including Holly Madison, Kendra Wilkinson and Bridget Marquardt. His polyamorous lifestyle was even documented in the E! reality show The Girls Next Door. However, despite his protests that marriage was not for him, Hef announced via Twitter in 2010 that he was engaged for a third time...to another Playmate named Crystal Harris, who is a whopping 60 years his junior.

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