An uncomfortable encounter. Holly Madison opened up about her first date with Hugh Hefner — and what happened afterward.
The former Playboy model, 41, appeared on the Monday, December 13, episode of the “Power: Hugh Hefner” podcast to discuss her early days as one of the late media mogul’s girlfriends. The Vegas Diaries author explained that she initially agreed to go out with the Playboy founder, who died at age 91 in September 2017, after another one of his girlfriends had left the mansion in 2001.
“I didn’t really know what went on with them sexually,” the Girls Next Door alum recalled. “I figured something, and I was prepared for that. I wasn’t prepared for what would eventually happen.”
Madison joined Hefner and some others for a club night, then the group returned home to the Playboy Mansion. The Dancing With the Stars veteran said she knew the evening wouldn’t be a “very traditional first date,” but she still “wasn’t necessarily expecting to have sex that night.”
According to the former Playmate, however, they did have sex. “I was wasted,” Madison continued. “He was literally pushed on top of me. 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.”
The Oregon native added that she had always “looked up to” Hefner, but the encounter left her worried what other mansion residents might think of her.
“It was more the group aspect that was really out of my comfort zone,” she explained. “That happened. Everybody knows it happened. … All of a sudden, it felt like everybody was going to know about me, and I was horrified by it.”
Madison has been outspoken about her time with Hefner since their split in October 2008, writing about their relationship and her life in the mansion in her 2015 memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
Earlier this year, the Holly’s World alum used the phrase “Stockholm syndrome” to describe the situation in the mansion. “I started to feel like I was in love with him,” she said during an April episode of the “Call Her Daddy” podcast. “I felt like I identified with him, he was complimenting me so much, I started, in my mind, started blaming all the other problems on the other women.”
Madison also participated in the upcoming A&E docuseries Secrets of Playboy, due out in January 2022. In a clip released earlier this month, the model recalled a moment when Hefner “flipped out” on her after she got a short haircut.
“I got to a point, not too far into my time there — I think it was, like, six months in — where I kind of broke under that pressure being made to feel I had to look like everyone else,” she recounted in the video. When she arrived at home with her new ‘do, she claimed Hefner “was screaming at me and said it made me look old, hard and cheap.”
Bridget Marquardt, who starred alongside Madison on The Girls Next Door, shared similar memories of the duo’s time with Hefner in the same clip. “Hef would be pretty abrasive in the way he said things to Holly,” the former Bridget’s Sexiest Beaches host, 48, said. “It was very frustrating to live with every day — all of the drama that was going on and the tensions. I could definitely see that she was getting depressed and sad, and her demeanor was starting to change.”
