Holly Madison Reveals 1st Date With Hugh Hefner Had an ‘Emotional Impact’ That Left Her ‘Mortified’

Former Playboy model Holly Madison recently revealed aspects of her first date with the late Hugh Hefner and the turmoil she felt afterward.

While the Girls Next Door alum, 41, knew her night out with the media mogul wouldn’t be a “traditional” first date, she still agreed after one of his girlfriends left the mansion in 2001. However, she was unprepared for “what would eventually happen.”

“[Hugh] was literally pushed on top of me,” Holly said on the Monday, December 13, episode of the “Power: Hugh Hefner” podcast. “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.”

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“I was wasted,” the Vegas Diaries author said. Holly and Hugh, who died at the age of 91 in September 2017, had joined others for a club night before returning to the infamous Playboy Mansion. She added she “wasn’t expecting to have sex that night.” 

The Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny author, who dated Hugh from 2001 to 2008, realized that the “group aspect” made her realize she was “out of [her] comfort zone.”

“That happened. Everybody knows it happened,” she said on the podcast. “All of a sudden, it felt like everybody was going to know about me, and I was horrified by it.”

Holly, who was referred to as Hugh’s No. 1 girlfriend on The Girls Next Door, has spoken about her time at the mansion and by Hugh’s side often since their split. In a preview for the A&E documentary Secrets of a Playboy, which will be released in January 2022, she revealed that the editor-in-chief of Playboy had “flipped out” on her when she returned with a short haircut. 

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The Holly’s World star wanted to look different from the other girls who cohabitated in the mansion and also dated Hugh, Kendra Wilkinson and Bridget Marquardt. 

“My hair was really long naturally, and I was just like, ‘I’m gonna go chop my hair off so I can, at least, look a little different,’” Holly explained, adding she came back with short hair. “He was screaming at me and said it made me look old, hard and cheap.” 

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While Holly’s co-bunny, Bridget, 48, has spoken highly in the past of Hugh, she admitted in the clip that he could be “pretty abrasive in the way he said things to Holly.”

“She came down with red lipstick one night, and he flipped out and said he hated red lipstick on girls, [and told her], ‘You need to take it off right way,’ even though other people could wear red lipstick, and it didn’t seem to bother him,” Bridget stated. “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.” 

Holly said, eventually, she was ready to move on with her life and away from Hugh. Hugh went on to marry Crystal Hefner (née Harris) in 2012.