Holly Madison dated Hugh Hefner from 2001 to 2008 and lived at the Playboy mansion and appeared with him on the E! Reality show, ‘The Girls Next Door’. She has now described how she felt while living with Hugh Hefner in the new A&E series ‘Secrets of Playboy’ whose first episode was released on 24th January 2022. Holly was 21-years-old when she first went to the Playboy Mansion and saw a wholesome atmosphere and craved a sense of community.
In the first episode of ‘Secrets of Playboy’, Holly Madison shared that she was not physically attracted to Hugh Hefner but she did find him very charming. Explaining how she had trouble connecting with people in her childhood, Holly said, "I think I was drawn to try and be in the spotlight because I felt like if I could be famous, that would be a shortcut to feeling a connection with people. I was very much attracted to the Anna Nicole Smiths, who was a supermodel at the time, and the Jenny McCarthys, who was the "It Girl" on MTV, and the Pamela Anderson's, who was the biggest TV star at the time. And the common denominator was they all started out as Playmates. It made a lot of sense to infer that if I start out at Playboy, I could end up like that too, because they did."
Holly while sharing about her experience at the Playboy mansion mentioned that she thought that it was gross that her ex and late Hugh Hefner did not want to use protection during group sex with her and other women. She went on to describe her first time having sex with Hugh and other women after they returned from a night out. Holly said, "There was definitely no romance or seduction or anything like that. It was dark in the room, but there was a giant movie screen of porn in front of the bed. He was in the middle of the bed, and then the women were surrounding him. I never had casual sex with anybody before. I feel like I was kind of really asexual, so maybe I just wasn't ready for that. It was all very mechanical and robotic, and you would kind of follow the other women's lead. The impact it had on me was so heavy. I never expected to be the first person to have sex that night or to be pushed into it."
During a podcast interview in April 2021, Call Her Daddy, Holly Madison shared that when she and Hugh first time had sex, he offered her Quaaludes and she was ‘wasted’. Holly said, “When I got up there, I was so wasted and thrown into it, that once it was done, there was something about the experience that made me feel very out of control.” Holly described the environment at the Playboy Mansion as ‘very cult like’ and added, "He comes across as caring and generous, especially when you see him in that atmosphere because he's providing this good time for all his friends and you know, there's a glow about him. And you just start to build this picture in your head of somebody who can really do no wrong. And now, looking back on my time at Playboy, it reminds me of a cult.”
Holly Madison further explained on reminding the mansion as a cult, "The reason I think the mansion was very cult-like is that we were all kind of gaslit and expected to think of Hef as like this really good guy. And you started to feel like 'Oh, he's not what they say in the media, he's just a nice man. Another thing that reminds me of a cult is how it was so easy to get isolated from the outside world there. You had a 9 o'clock curfew. You were encouraged to not have friends over — you weren't really allowed to leave unless it was like a family holiday."
Sharing about the sexual activities that took place at the mansion, Holly said that sex always happened kind of like the same time the same night. She added, “We would go out to a club every Wednesday and Friday and that would be expected when we got home. I kept my waitressing job just like one day a week because I wanted just to have something easy to go back to should things not work out and he said it made him jealous and he would appreciate it if I quit my job. So instead, we were given $1,000 a week as an allowance."
She also shared that getting plastic surgery amongst the women at the mansion was ‘compulsive’ and everybody was doing it and felt like she needed to look exactly like them. In one of her previous interviews, Holly had shared, "I've always been very honest about [plastic surgery]. I've had my boobs and my nose done."
On asking if she was ever in love with Hugh Hefner, Holly Madison said that she thought she was in love but it was very Stockholm syndrome. She added, “I never blamed him for any of the drama that went on and always blamed it on the other women. Hef was innocent in my eyes. And then later, one of the girls was telling me how Hef always pits the main girlfriend against the other girls. This situation was going on for years before I came along."