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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.
Marilyn Cole, Karen Christy and Lillian Mueller being some of the notable Playmates whose relationships with Hefner fall into that category.
Barbi Benton (1969-1976) She landed a role on "Playboy After Dark" where she met Hugh Hefner.
Mildred Williams (1949-1959) Hefner met Mildred Williams in college and they got married in 1949. Williams had revealed that she had an affair while Hefner was serving in the army.
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.
network reality television series The Girls Next Door.
Despite their "girlfriend" status, Karissa said the relationship she and Kristina shared with Hefner was more for fun and the opportunity to be on the show, rather than romance.SLIDESHOW: The Handsome and Always Talented Hugh Hefner However, the sisters ignored his warnings, prompting him to send them packing. That was the absolute number one rule -- no boys allowed. SLIDESHOW: Karissa and Kristina Shannon Karissa Shannon said: "After a couple of weeks, Hef was getting a little bit upset about the boyfriends, so he wanted us to move out. Over the course of their seven years together, their untraditional relationship was chronicled on E!'s series, While the magnate expected to spend the rest of his life with her, a point of contention popped up between them when Madison expressed desire to marry the late star and start a family. I kind of didn't want to put a generic statement out there like 'Congratulations!Of the many women to come in and out of Hugh Hefner's life, Holly Madisonis one of the most famous.Tags: Adult Dating, affair dating, sex dating