How old was Holly Madison when she dated Hugh Hefner? TV personality speaks about adult activities at the Playboy Mansion that she "hated"
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Holly Madison (Photo: Everett Collection)TV personality Holly Madison opens up about adult activities at the Playboy Mansion that she "hated." During her appearance on the In Your Dreams with Owen Thiele podcast last Friday, Madison detailed dating Playboy magazine founder and editor-in-chief Hugh Hefner.
The pair were in a relationship for almost eight years between 2001 and 2008. Notably, Madison was 22 to Hefner's 75. During the time together, she stayed at the latter's Playboy mansion in Los Angeles, where he was known to live with his multiple girlfriends.
When questioned about their intimate life, The Girls Next Door star told Thiele:
"It's a very different story between when we were by ourselves than with everybody else in the room."
Elaborating on her thoughts about the group s*x, Madison continued:
"Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it."
Holly Madison compared her time at the Playboy Mansion to being a "goldfish in the goldfish bowl"
During her podcast interview, Holly Madison pointed out that her 53-year age gap with Hugh Hefner didn't affect their coupling. She told host Owen Thiele that it was "more normal than you would think," much to the latter's surprise. Agreeing that it was a common misconception, the 45-year-old explained:
"There was a time when I couldn't post anything (on social media) without some dumba** in the comments (being) like, 'Oh, old b*lls.'"
The TV personality continued to add that the Playboy founder kept the lights off, so she is not an authority on the subject.
Elsewhere in the interview, Holly Madison, known for her love for horror, addressed rumors that Hugh Hefner's sprawling L.A. mansion is haunted. She jokingly noted:
"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."
Madison told Thiele she was written into Hugh Hefner’s will before she left the lifestyle behind. The 45-year-old revealed that while packing to move out of his estate following their split, she found a folder on the bed. Noting that she was the "biggest snoop in the house," she elaborated on finding he was leaving $3 million to her name.
"It was kind of sad though, because I'd already broken it off with him, and he was trying to get me to stay. So it was kind of like a low-key bribe but also sad because he can't, like, sit me down and talk to me about it," Holly Madison recalled.
This is not the first time Holly Madison has spoken about her time spent at the Playboy Mansion. During a sitdown with People magazine in March, she spoke about the strange things she saw around the house. This included trays with "makeshift lube." She recalled:
"They would have these trays everywhere, like in every bathroom, out on the tennis courts, by the pool, and it would be a tray with Kleenex, Pepto Bismol, Vaseline, baby oil, sunscreen — any kind of makeshift lube."
However, she asserted that the negative parts of her experience were related to her "relationship dynamics" with Hefner and the other girls. " Calling it a "multifaceted" experience, Holly explained that she "enjoyed" posing for Playboy. She even recalled working at the studio "producing the playmate pictorials" for a couple of years.
Last week, in an interview with NY Post, Holly Madison called the Playboy mogul a "master manipulator." Reflecting on her mindset with dating him, she explained it felt like being in love "tinged with a little bit of Stockholm syndrome."
"So I look back and I just see somebody who was young and impressionable and just kind of in a fog almost," she told the outlet.
Comparing life at the Playboy mansion as being a "goldfish in the goldfish bowl," she added:
"You know, when you’re in the goldfish bowl, everything looks all blurry and distorted. And you don’t see things clearly until you’re outside of the goldfish bowl."
During her time with the brand's founder, Holly Madison starred in the reality show The Girls Next Door, which documented the life inside the mansion alongside models Bridgette Marquardt and Kendra Wilkinson. Following Hefner's death in 2017, Marquardt, Wilkinson, and others have opened up about the dark side of dating him.
In 2015, Holly Madison wrote her memoir Down the Rabbit Hole, where she detailed accounts of verbal and emotional abuse during her time at the Playboy Mansion. She recounted the same in the 2021 A&E docuseries Secrets of Playboy. She called Hafner "pretty abrasive" and noted living at the estate was a "cycle of gross things."
In a May 2025 article, Fox News, citing an interview with the TV personality, reported she wanted young models-in-the-making to look at the "cautionary tales" of others, like herself, before entering the industry.
Holly Madison is currently awaiting the release of season three of her true-crime show, The Playboy Murders. The series centers around high-profile tragedies and crimes associated with the Playboy brand. It premieres on Monday.
TOPICS: Holly Madison, In Your Dreams with Owen Thiele, Hugh Hefner, Owen Thiele, Playboy