Holly Madison Recalls ‘Traumatic’ First Night With Hugh Hefner at Playboy Mansion: ‘I Was Horrified’

Holly Madison is opening up about the “traumatic experience” she had the first night she spent with Hugh Hefner at the Playboy Mansion. The former Girls Next Door star, 41, discussed the complexities of her relationship with Hefner, who died in 2017, on the Power: Hugh Hefner podcast, saying that when she was first invited for a night out with Hefner, she was both hoping for an invite to live at the mansion at “nervous” about what happened next. 

“I didn’t really know what went on with them sexually,” she said. “I knew there must be something and I was prepared for that. I wasn’t prepared for what would eventually happen.” Madison, who dated Hefner from 2001 to 2008, said the night ended when Hefner took her and some other women back to the mansion. The former Playboy model noted she wasn’t “necessarily expecting” to have sex that night, thinking it would be “more of a first date,” despite the unconventional circumstances.

“I thought it would be more the type of thing where I saw what happened, saw what was going on. If I wasn’t comfortable with it I wouldn’t have to do anything and I could make my decision on whether I wanted to come back for date number two or not,” she said. However, Madison continued that things moved forward more quickly than she expected. 

“I definitely was not expecting to be the first one to go that night but I was wasted,” she said. “He was literally pushed on top of me. And after it happened, I was just mortified and embarrassed and it had way more of an emotional impact on me than I thought it would.” While Madison had “always admired” Hefner, and wasn’t “repelled” by the idea of having sex with him, she was “horrified” that other people would know what had happened.

“It was more the group aspect that was really out of my comfort zone and just the feeling of ‘Wow, OK, that happened. Everybody knows it happened,’” she recalled. “I kind of all of a sudden felt like everybody was going to know about me, and I was horrified by it.” It was that dynamic that convinced her she had no option but to stay.

“I felt like, ‘There’s no taking that back so I might as well get what I came for,’ ” she said, revealing that the next morning Hefner agreed to let her move into the mansion. “I felt like by moving myself in and getting what I wanted from the situation, that was demanding respect in a way. I felt like if I didn’t do that I was just going to be haunted by this experience.”