Holly Madison says the Playboy Mansion’s group sex nights ran like a rotation. Your turn, about two minutes each, then the next girl. She called it “part of the job.”
Video: Holly Madison on Let’s Be Honest with Kristin Cavallari (May 5 episode).
Madison, Hugh Hefner’s No. 1 girlfriend from 2001 to 2008, described the routine on the May 5 episode of the Let’s Be Honest podcast with Kristin Cavallari. A clip from the interview has been recirculating on social media. Hefner died in 2017 at age 91 and cannot respond to her account, so what follows is Madison’s telling of it.
Madison said most of the other girls Hefner met at nightclubs, or while testing to become Playmates, or they came to the parties. Women wanted into that world, she said, and he did not have to do much recruiting because there was always a girl in the group steering girls his way, with lines like “here, have another drink” and “I want to come hang out upstairs.”
Asked if there was a drink limit, Madison said no. The girls could get wasted, she said, and he did not care. She said he handed out Quaaludes. Madison said she confronted him about it, worried he would meet a girl at a club, not know what she had already had that night, and hand her a Quaalude, picturing the scene in Boogie Nights where a girl overdoses and gets left outside a hospital. He answered, she said, that it was a concern, and that he had a whole team of people to deal with it, so he did not have to.
All of the girls who lived in the house while she was there were girlfriends, Madison said. Women testing to become Playmates, shooting pictorials, or working for Playboy stayed in the guesthouse. Rarely, she said, someone got one of the rooms upstairs for a short stay.
The nights themselves, she said, were “kind of like taking turns.” The girls who were not active with him acted like they were active with each other, “but not really.” Giant screens played porn. The girls talked with each other. “It was a really weird scene,” Madison said. “Nobody liked it and everybody tried to just get it done as fast as possible.”
As the main girlfriend, Madison said there was no set order for first or last. “There wasn’t really an order necessarily,” she said. “It was kind of the same every night, but kind of not. Just like, here we go. Part of the job.”
In the beginning, she said, they went out twice a week, and it was always after going out. Once filming started on the reality show, the regular Wednesday and Friday club nights stopped, she said, which was amazing. After that they only went out for special occasions.
Related: https://stopsimpingnow.com/he-told-the-court-she-cheated-then-both-sides-agreed-it-never-happened/
Sources: Let’s Be Honest with Kristin Cavallari, May 5 episode; USA Today, May 9, 2026.