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.She wanted spontaneity—maybe a "quiet dinner together" or a visit to a "piano bar—and time away from the prying eyes of guests. I'd say I want to go to bed and get up at and work out. He doesn't like to be alone." story: Tuesday nights, family time with Conrad and the boys.

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"I'm the leader of a Girl Scout camp," he once said.

A sign on the mansion's driveway forever promises "Playmates at Play." But this carefree image is at odds with the essential character of a workaholic obsessive who sets exacting terms for how he and his paramours should have their fun. (Necessary, Hef told the With the caveat that it's tough to know the inner workings of any relationship (let alone a four-way one), there doesn't seem to be any one reason why Hef's relationships end.

I will miss him so much but he will be in my heart forever.’ Can't really put in to words how I really feel.

It's easy to say he will be missed and how much I loved him.

Several others, after leaving the mansion, have expressed ambivalence about its chapter in their lives.

Kendra Wilkinson, who starred as one of Hef's girls on that she saw Hefner infrequently when she lived with him and added that they never went on "solo dates." She said she was now "totally against" group dating, and spoke of Hefner with a kind of mixed gratitude.There's a lot more than that — Kendra Wilkinson (@Kendra Wilkinson) September 28, 2017 The Playboy founder died peacefully at this home surrounded by his loved ones.The 91-year-old has had declining health in the last year and has not been seen in public for some time.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.The story borrowed heavily from a four-year-old tell-all written by a disgruntled former girlfriend named Izabella St. Still, it's enough to make one wonder: What must it be like to be married to Hugh Hefner?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.