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They met at Northwestern University. When Hefner and Roderick broke up, he added a bigger rotation of girlfriends, including Izabella St. James moved into the Playboy Mansion in and lived there for two years. Though she broke off their engagement before their planned wedding, the two were eventually wed in December Carrie Leigh lived with and dated Hefner for five years in the '80s before leaving him. The couple stayed together for a another decade, but divorced in

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Aryana. Age: 25.
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Since Hefner's death, Harris deleted her Instagram and her Twitter account has been set to private.

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Millie. Age: 21.
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Mandy Marie - Playboy Nude Girl

Conrad and Hefner had two children, Marston and Cooper. Leigh filed three lawsuits against Hefner after they broke up, including one for publishing unauthorized photos of the model. Madison is married to Pasquele Rotella and they have two children. Shannon Tweed dated Hefner briefly after being named Playmate of the Year. Hugh Hefner married his first wife Mildred Williams in Since Hefner's death, Harris deleted her Instagram and her Twitter account has been set to private. From the time Hefner and Conrad separated in , he dated a multitude of Playmates, including actress Brande Roderick.

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