Curious about what went on behind the closed doors of the Playboy Mansion? In a recent podcast appearance, Holly Madison’s revelations about Hugh Hefner have once again stirred curiosity. The former Playboy model didn’t hold back as she opened up about her uncomfortable and complex experiences during her relationship with the late Hugh Hefner.
Holly Madison comments on Hugh Hefner relationship
Holly Madison, who famously dated Hugh Hefner from 2001 to 2008, recently shared details about their intimate life on Owen Thiele’s podcast In Your Dreams.
She recalled moments she found particularly disturbing. According to Madison, the one-on-one moments with Hefner were modest. However, the group encounters inside the Playboy Mansion left her feeling disgusted and emotionally disconnected.
She described the group bedroom experiences as something she “hated” and clarified she was vocal about her discomfort at the time. “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,” Madison said. She added that those experiences impacted her in ways she didn’t fully understand until later.
Despite their significant 53-year age difference, Madison said that being alone with Hefner felt more “normal” than most would assume. She even addressed some of the awkward public commentary she received post-relationship. “Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing,” she joked, later noting that she and Hefner usually kept the lights off during intimate moments.
Madison also spoke about the psychological hold Hefner had over her. In an interview with The New York Post, she admitted to being in an emotional fog during their relationship, one clouded by manipulation. She likened her experience to Stockholm syndrome and reflected on how she mistook control for connection. Madison also expressed regret over her past naivety and acknowledged that she had idealized Hefner without truly knowing him. She said, “I had this mindset of being in love. And it was kind of tinged with a little bit of Stockholm syndrome.”
Originally reported by Harshika Bhatia on ComingSoon.
