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Hugh Hefner's ex Holly Madison reveals the one specific 'rule' they were forced to follow in Playboy Mansion
Home>Celebrity>News
Published 17:59 18 Nov 2025 GMT

Hugh Hefner's ex Holly Madison reveals the one specific 'rule' they were forced to follow in Playboy Mansion

Holly Madison notoriously dated Hugh Hefner in the 2000s

Britt Jones

Britt Jones

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Featured Image Credit: Chad Buchanan/Getty Images

Topics: Hugh Hefner, Celebrity, US News

Britt Jones
Britt Jones

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Hugh Hefner’s ex-girlfriend, Holly Madison, claimed there was one 'fixation' he had which would make him 'mad' if it wasn't done.

Madison, 45, was Hefner’s ‘number one girlfriend’ when she spent her life living in the lavish home in the 2000s, until the pair called it quits in 2009.

The LA residence was known around the world and was often filled with people, including celebrities, until Hefner passed away at 91 in 2017.

Madison, along with Hefner's two other girlfriends, Bridget Marquardt and Kendra Wilkinson, were launched into stardom with the debut of their reality TV show on E!, titled The Girls Next Door.

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While the TV show looked into their lives at the Playboy Mansion, the Holly's World star has spoken out about what it was really like to be with such a man.

Holly Madison dated Hugh Hefner from 2001 to 2009 (J. Merritt / Contributor/ Getty Stock)
Holly Madison dated Hugh Hefner from 2001 to 2009 (J. Merritt / Contributor/ Getty Stock)

Speaking on the In Your Dreams Podcast with Owen Thiele, she talked about their sex life, which she described as 'normal' despite their 50-year age gap, and when it was just the two of them.

She said: “Well, it's a very different story between when we were just by ourselves than with everybody else in the room. Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it.

“If it was just me and him, it was a lot more normal than you would think.”

In an interview on the Call Her Daddy podcast in 2021, she opened up more on the ins and outs of their love life, and revealed that Hefner had a certain 'fixation' when it came to the girl's genitals.

Madison said: "He always had a fixation on everyone always being fully shaved," adding: “He would get mad if somebody wasn’t shaved.”

Madison opened up about what went on in the bedroom (Robert Mora / Staff/ Getty Stock)
Madison opened up about what went on in the bedroom (Robert Mora / Staff/ Getty Stock)

She also said that he ‘always liked vaginas to look a certain way’, with ‘nothing sticking out’, and in terms of how it usually went, Hefner was 'always laying down' so the girls would often have to get on top.

When it came to her experiences in the mansion, which she'd previously revealed 'wasn't always in the best shape', Madison said that she'd try and put a positive spin on it, claiming it was an 'easy way to dismiss everything, and tie my experiences up in a nice little bow'.

In her 2015 memoir, she claimed that Hefner was ‘controlling’ through their relationship and she was ‘miserable’.

Madison said that she noticed the other girlfriends were seemingly going through a 'similar experience' to her, as she could 'tell something was a little wrong, even though they were trying to have a great experience'.

She added: “I could always see that there was a little bit of sadness behind their eyes, or they seemed a little upset, and I never really knew why, but I always kind of had a suspicion that maybe they had a similar experience to me.”

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