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(Over the years, Hef's stable of live-in lovers has waxed and waned, with seven apparently being about what he can handle.
At times it is has been smaller, as when Hef dated a tight-knit trio consisting of a Brande and twins named Mandy and Sandy.) Hefner has worked hard to portray his lifestyle as one of perpetual play, in which he figures as a sort of benevolent daddy to a happy troop of never-aging, nearly interchangeable, constantly cavorting girls.
Like Conrad, at least some of Hefner's live-in girlfriends have chafed under his rules, resenting what one called a "strict" mansion lifestyle in which staffers would log the girlfriends' comings and goings. Some recent girlfriends have moved on to other men and different careers (reality shows, topless burlesque).
According to Hefner, one girlfriend, Holly Madison, wanted to marry him and was crushed when he declined.
He used to say—more than a little implausibly—that he and former No. After their breakup, Hefner noted in an interview that "there are girls lined up outside the front gate." author Watts explains that he has long held his girlfriends to a sexual double standard.
1 Madison, a onetime Hooters girl, were brought together by their shared love of Bix Beiderbecke's 1920s jazz work. They are expected to be faithful to him, while he gets to do whatever he likes.
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He gave her an engagement ring inside a In interviews, Harris says she doesn't even notice the age difference.So why, given all of this, would anyone want to marry Hugh Hefner? 1, a position Hef usually confers on one girlfriend when he's dating a pack.The revolving door of girlfriends points to one possible motive for becoming Hef's wife: security. This title is determined, Hef has said by "seniority" and common interests.iographies, profiles, and interviews suggest the answer is: probably pretty boring. Hefner has been married twice before—in 1949 to high-school classmate Millie Williams, with whom he had two children, and in 1989 to Playmate Kimberley Conrad, with whom he had two more.
The Playboy mansion comes across not so much a prison as a singularly unsexy place of strict routines, tight curfews, and old movies. His marriage to Williams lasted 10 years, and according to University of Missouri historian Steven Watts was undone by a basic incompatibility as well as by Hef's open dalliances with other women.
had run a piece describing the Mansion as a "squalid prison" run by a controlling senior citizen who, amid decaying surroundings, doled out weekly allowances to his girlfriends and kept sex parties tightly scheduled.