Reality star Holly Madison has a complicated view of her time dating Playboy magazine founder and editor-in-chief Hugh Hefner. But she unequivocally “hated” some things she did while living at the Playboy Mansion.
During a playful conversation on a recent episode of the In Your Dreams with Owen Thiele podcast about rumors that the sprawling Los Angeles estate is haunted, Madison darkly joked, “I really love that stuff, so I always thought that was kind of intriguing and fun. The scary stuff is some of the other girls you have to deal with, or what’s going to happen in the bedroom on night two.”
When asked if Hefner, with whom she had an eight-year relationship and who was 75 to Madison’s 22 when they began dating in 2001, was good in bed, Madison said, “It’s a very different story between when we were by ourselves than with everybody else in the room.”
And when other residents and guests of the Playboy Mansion were present? “That was disgusting. I hated it. I made it very known I hated it,” Madison revealed.
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Madison became a fixture of aughts pop culture when she began starring on The Girls Next Door, a reality show chronicling life inside the Playboy Mansion, alongside fellow Playboy models Bridgette Marquardt and Kendra Wilkinson.
After Hefner died in 2017 at the age of 91, Madison, Marquardt, Wilkinson, and others began speaking out about the dark side of dating Hefner and living in the Playboy Mansion.
In the 2021 A&E docuseries Secrets of Playboy, Madison recalled Hefner “screaming at me” that a haircut “made me look old, hard, and cheap.” Marquardt said that “Hef would be pretty abrasive in the way he said things to Holly” in particular, with Madison remembering, “There were times probably within the first couple years that I lived there when I felt like I was just in this cycle of gross things and I didn’t know what to do.”
Madison told Thiele, “If it was just me and him, it was very, like, a lot more normal than you would think,” adding that “everybody has this horror story” in their minds of “how gross an old man’s body must be.”
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“I feel like there was a time when I couldn’t post anything without some dumbass in the comments like, ‘Oh, old balls,’ or something like that,” she said. “Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”
She also revealed she was asked to join the cast of the first U.S. season of the reality series The Traitors, but passed on the opportunity.
“It hadn’t been on the air so I didn’t know what it was, and I thought that they thought I was a traitor because I wrote a book about Hef,” Madison said, referring to her 2016 book The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention, which details the ups and down of her time with Hefner. “I was like, ‘I’m not falling for that, I’m not going on your stupid show where I’m supposed to be a villain cuz I’m a traitor, f— you. So I didn’t do it, but now I regret it.”
Watch the rest of Madison’s In Your Dreams podcast interview above.
