Holly Madison thought she knew what she was getting herself into when going on her first date with Playboy mogul Hugh Hefner, but things took a very disturbing turn.
While chatting on the Power: Hugh Hefner podcast on Monday, the 41-year-old admitted that she first agreed to go on a date with Hefner after another one of his girlfriends left the mansion in 2001. While she didn’t know exactly what went down behind closed doors, she didn’t expect things to get intimate so quickly, saying:
“I didn’t really know what went on with them sexually. I figured something, and I was prepared for that. I wasn’t prepared for what would eventually happen.”
Madison joined Hef and a few other women at a club that evening. They returned home later that night, and the Girls Next Door alum remembered being very drunk at that point.
Holly wasn’t naive — she knew her time with Hef was never going to be a “very traditional first date.” That said, the model “wasn’t necessarily expecting to have sex that night.” Unfortunately, she shared, they did:
“I was wasted. 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 had always “looked up to” the businessman, and they would go on to have a years-long “abrasive” relationship (until they split in 2008). It doesn’t seem like the sex changed her feelings toward him, but it did make her fear how the other women would react to the news, explaining:
“It was more the group aspect that was really out of my comfort zone. 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.”
Earlier this year, the Holly’s World alum described herself as having “Stockholm syndrome” while coupled up with Hefner, who died in 2017 at 91. In an interview on the Call Her Daddy podcast, the reality TV star said:
“I started to feel like I was in love with him. 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.”
TBH, it sounds like the problems started during that very first date. So sad that she had to deal with that.
Since Holly left the mansion, she’s been incredibly open about what went down in the famous home. Not only did she pen her 2015 memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, but she stars in A&E’s upcoming docuseries, Secrets of Playboy, in which she’ll help expose some of the empire’s darkest secrets.
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