Holly Madison Says Hugh Hefner Was "Literally Pushed on Top of Me" During Their First Date

"I wasn't prepared for what would eventually happen," Holly Madison recalled about her first date night with Hugh Hefner, and the "fear" she experienced after they allegedly had sex.

By Alyssa Morin Dec 15, 2021 2:01 AMTags

Holly Madison is reflecting on her past romance with the late Hugh Hefner.

The Girls Next Door star, who dated the Playboy magazine founder between 2001 and 2008, recently opened up about the early days of their relationship. Speaking on the Power: Hugh Hefner podcast during the Dec. 13 episode, Holly recalled her first date with the late media mogul, who passed away in 2017 at the age of 91 after going into cardiac arrest and suffering respiratory failure.

According to Holly, she initially agreed to go out with Hugh after there was a "spot open" when one of his girlfriends had left the mansion in 2001.

"I didn't really know what went on with them sexually," the Vegas Diaries author said. "I figured something, and I was prepared for that. I wasn't prepared for what would eventually happen."

She continued, "I wasn't necessarily expecting to have sex that night. I thought it would be more of a first date."

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Although Holly said she didn't expect for it to be a "very traditional first date," she believed that "it would be more of a type of thing where I saw what happened, saw what was going on, [and] if I wasn't comfortable with it, I wouldn't have to do anything."

Denise Truscello/WireImage.com

According to Holly, that wasn't what happened that evening.

"He was literally pushed on top of me," she recalled of the alleged encounter. "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."

Holly explained that she "had always admired Hef" and had "really looked up to him" long before she became one of his girlfriends. But what worried her the most about their alleged encounter, she said, was what others in the Playboy mansion would think about it.

"It wasn't that the idea of possibly having sex with him repelled me so much," she said. "It was more the group aspect that was really out of my comfort zone and just the feeling of like, 'Wow. That happened. Everybody knows it happened.'"

According to Holly, she had this "fear of 'well, everybody knows it,'" adding, "All of a sudden it felt like everybody was going to know about me and I was horrified by it." 

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When discussing why she didn't just "run away" after their first date, Holly explained her reasoning for staying, saying, "I felt like there's no taking that back, so I might as well get what I came for."

This isn't the first time Holly has opened up about her time with Hugh and living in the Playboy mansion. She detailed her experience in her 2015 memoir, Down the Rabbit Hole, as well as her Vegas Diaries memoir in 2016.

In August, A&E teased a clip from its upcoming docuseries, Secrets of Playboy, in which Holly called joining Hugh's world a "dangerous choice."

Earlier this month, Holly said in a new teaser, "I remember there were times probably within the first couple years I lived there when I felt like I was just in this cycle of gross things and I didn't know what to do."

E! News has reached out to an attorney who represents the Hefner estate for comment but hasn't heard back.

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