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They divorced in 1959 after a decade of marriage.'s "Playmate of the Month" in January 1988, married Hefner in 1989. The couple had two children together: Marston, born in 1990, and Cooper in 1991.After nine years of marriage, they legally separated and eventually divorced in 2010.Crystal Harris (2012 - 2017) Crystal Harris and Hugh Hefner got married on New Year's Eve in 2012. He was 86-years-old and she was 26-years-old at the time.
He's said: “That was the most devastating moment in my life." According to Hefner, his wife would let him sleep with other women to make up for her infidelity. Various women -- and men Being, well, a playboy, Hef's love life can't simply be summed up with a list of "relationships" because he had numerous trysts that weren't so structured, with both women and men, including "maybe eleven out of twelve months' worth of Playmates" for a number of years after his divorce from Mildred.Following Hefner’s passing, Wilkinson tweeted “Can’t really put in to words how I really feel.”, Hefner invited twins Kristina and Karissa Shannon to move into his mansion and be a part of the show. He reportedly broke up with them after finding out they had younger boyfriends come inside the home. To bring you the best content on our sites and applications, Meredith partners with third party advertisers to serve digital ads, including personalized digital ads.According to People, the two lived together for nine years and Hefner has said “I only regret not marrying Barbi,” said Hefner, “because it finally led to our going separate ways."Kendra Wilkinson (2004-2008) While dating Holly, Hefner was also dating Kendra and Bridget who were all cast members on "Girl's Next Door." Kendra also detailed how she would often cheat on Hefner while they were together.Kristina and Karissa Shannon 2008-2010) The twins moved into the mansion in 2008 and were also part of "The Girls Next Door." Hefner apparently kicked them out of the mansion for having younger boyfriends come over.