Holly Madison Details ‘Weird’ Group Sex Nights With Hugh Hefner

Nearly two decades after walking away from the Playboy Mansion, Holly Madison is still filling in the details of what life there was actually like — and a lot of it was deeply uncomfortable.

The Girls Next Door alum sat down with Kristin Cavallari for a May 5 episode of the Let’s Be Honest podcast and opened up about the group sex nights that Hugh Hefner would orchestrate at the mansion — experiences she described as something everyone just wanted to survive.

“It was a really weird scene. Nobody liked it and everybody just tried to get it done as fast as possible,” Madison told Cavallari. “It was a nightmare.”

She explained that the encounters typically followed their regular Wednesday and Friday club nights. “At the beginning, we’d go out twice a week and it would always be after we’d go out,” she said. “There wasn’t really an order necessarily. It was kind of the same every night but kind of not. It was just, ew.”

The dynamic in the room, she said, was more awkward than anything else. “Kind of like taking turns and then the girls who weren’t active with him were kind of like acting like they were active with the other girls, but not really,” she recalled. “It would be kind of silhouetted because you’d have, like, these giant screens of porn going and it would be just girls like talking s**t with each other.”

One-on-one nights, by contrast, were almost shockingly mundane. “It would just be us watching a movie or he’s doing a crossword puzzle and I’m reading,” she said. “It was very suburban.”

How ‘Girls Next Door’ Changed Everything

The group sex nights didn’t end because of a conversation or a confrontation. They just… stopped — and Madison credits the cameras.

Once filming began on The Girls Next Door, the E! reality series that followed Madison, Bridget Marquardt, and Kendra Wilkinson through six seasons from 2005 to 2010, the schedule shifted and the club nights tapered off. Without the club nights, the group sessions stopped happening.

“He loved the show. He was like high off the show,” Madison speculated. “It gave him new relevance, like the ego boost. So he didn’t really feel the need to like, ‘Oh, I have to do these compulsive sex nights to make myself feel wanted and relevant,’ I think.”

And the three women were quietly, collectively relieved. “Me, Bridget, and Kendra were all on the same page that we just didn’t want to do that anymore,” Madison said. “Nobody had to say anything. We were just like, ‘OK, we’re not going out anymore so nobody’s going to initiate it.’”

Toward the end of her time with Hefner — she left in 2008 after seven years — sex had become rare altogether. “Very rarely,” she said simply.

The Will on the Bed

Madison also revealed something that speaks to just how calculated the manipulation at the mansion could be. When she told Hefner she wanted to leave, he didn’t take it seriously — and his tactics to keep her there were quietly unsettling.

“He kept trying to get me back,” she said. “He would leave his will out on the bed on my side so I could see how much money was going to be left for me if I stayed.”

That wasn’t the only pressure. After Madison and Wilkinson announced they were leaving, tabloid outlets ran pieces predicting the women would fade into irrelevance without the Hefner name attached to them. Hefner, she says, used that too. “He would get all this stuff printed out and leave it out so I would see, hoping I would change my mind, like, oh my god, I can’t be irrelevant. I must stay.”

A Pattern of Speaking Out

None of this is the first time Madison has pulled back the curtain. In the 2022 A&E docuseries Secrets of Playboy, she described the mansion as cult-like and called her first sexual experience with Hefner traumatic. “It was very Stockholm syndrome,” she said at the time.

Last year, she was even more blunt on the In Your Dreams podcast: “Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it.” And in a separate 2025 interview with Page Six, Madison revealed she believes her undiagnosed autism made her more susceptible to falling for Hefner — who was more than five decades her senior — and to tolerating conditions at the mansion she otherwise might have walked away from sooner.

Hefner died in September 2017 at age 91. His son Cooper responded to the 2022 docuseries on X, writing that his father “was not a liar” and calling the accounts “a case study of regret becoming revenge.” Playboy Enterprises, for its part, issued a statement that same month: “Today’s Playboy is not Hugh Hefner’s Playboy… We trust and validate these women and their stories.”

Madison, now a mom of two and the author of Down the Rabbit Hole, has been consistent in her account across years of interviews. On the Cavallari podcast, she wasn’t dramatic about any of it — just matter-of-fact, the way someone sounds when they’ve processed something fully and no longer need to soften it for anyone’s comfort.