The former “Girls Next Door” star dished all the X-rated details in a new interview with Kristin Cavallari.

Holly Madison breaks down ‘weird’ group sex with Hugh Hefner: ‘Nobody liked it’

The former "Girls Next Door" star dished all the X-rated details in a new interview with Kristin Cavallari.

By Kathleen Perricone

May 8, 2026 5:30 p.m. ET

Kendra Wilkinson, Bridget Marquardt, Hugh Hefner, and Holly Madison. Credit:

Carlo Allegri/Getty

- Holly Madison dishes on "weird" group sex with Hugh Hefner, then in his 80s, at the Playboy Mansion.

- "Nobody liked it and everybody tried to just get it done as fast as possible," she told Kristin Cavallari on the *Let's Be Honest* podcast.

- *The Girls Next Door *star was one of three of Hefner's main girlfriends for several years until 2008.

Being one of Hugh Hefner’s many girlfriends wasn’t exactly the most pleasurable experience.

Holly Madison, the *Playboy* founder’s No. 1 girl for seven years, broke down how she and the other ladies managed the required group sex with the octogenarian on the latest episode of *Let’s Be Honest With Kristin Cavallari*.

It began with Hefner’s three main partners — Madison, Bridget Marquardt, and Kendra Wilkinson — who starred on the E! reality series, *The Girls Next Door*, for five seasons beginning in 2005.

But over their years living under Hefner’s roof at the Playboy Mansion, multiple other women were invited into his bedroom, which caused “a really weird scene,” Madison said.

Hugh Hefner surrounded by a bevy of women in 2007.

Chad Buchanan/Getty

So was there a method to the madness?

“Yeah, kind of like taking turns and then the girls who weren’t active with him were kind of like acting like they were active with the other girls, but not really,” explained Madison, now a mother of two.

“It would be kind of silhouetted because you’d have, like, these giant screens of porn going and it would be just girls like talking s--- with each other,” she continued. “And it was a really weird scene and nobody liked it and everybody tried to just get it done as fast as possible.”

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Madison, who became Hefner’s girlfriend in 2001, revealed that being his No. 1 didn’t always translate to being the first to lay down with him.

And as the years went on, Madison claimed that she and the other two main girlfriends (Marquardt joined in 2002, followed by Wilkinson in 2004) were able to let the newbies handle the majority of the bedroom duties.

The frequency also changed too, fortunately.

Madison claimed that, before *The Girls Next Door* premiered in 2005, the three girlfriends were required to go on “date nights” with Hefner, then in his late 70s, every Wednesday and Friday. After hitting a nightclub, they would all head back to the mansion where Madison claims she, Marquardt, and Wilkinson were expected to have sex with Hefner.

Inside the Playboy Mansion in 2004.

Paul Harris/Getty

“But after we started filming the show, that just stopped, which was amazing,” Madison recalled.

*The Girls Next Door* was an instant hit for E!, breaking several ratings records in its first three seasons and reviving Hefner’s 50-year-old *Playboy* brand.

“He loved the show. He was like high off the show,” Madison told Cavallari. “It gave him new relevance, like the ego boost. So he didn’t really feel the need to like, ‘Oh, I have to do these compulsive sex nights to make myself feel wanted and relevant,’ I think.”

'The Girls Next Door': Holly Madison, Bridget Marquardt, and Kendra Wilkinson.

GABRIEL BOUYS/AFP via Getty

And when he did feel up to it, so to speak, there were other girlfriends around the Mansion who could perform the job.

“I think me, Bridget, and Kendra were so on the same page that we just didn’t want to do that anymore,” Madison said of the sexual evolution. “Nobody had to say anything. We were just like, ‘Okay, we’re not going out anymore.’”

And any one-on-one nights with Hefner were relatively tame. “It would just be like us watching a movie or he’s doing a crossword puzzle and I’m reading,” Madison said. “It was very suburban.”

For the final season of *The Girls Next Door* in 2009, Madison, Marquardt, and Wilkinson were no longer “dating” Hefner but still appeared on the show, which shifted focus to their replacements: Crystal Harris, who went on to marry Hefner in 2012, and 19-year-old twins Kristina and Karissa Shannon.

In the years since the *Playboy* founder died in 2017 at the age of 91, Madison and Marquardt have continued sharing their wildest stories with him on their *Girls Next Level* podcast.

But as for Wilkinson, Madison said she hasn’t spoken to her in over a decade and claimed the rift started after the show ended and the two got their own spinoffs, *Kendra* and *Holly’s World*, respectively.

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Wilkinson “was really wrapped up in the tabloid cycle,” Madison claimed, alleging that if Wilkinson "needed a feud to be mentioned that week, she would say she was never friends with me and I called her out on that over text.”

Madison alleged that Wilkinson tried to downplay her comments, which Madison rejected. “‘No, it’s not nothing, like, I think you’re being really f---ing fake right now,’” Madison claimed she told Wilkinson, alleging that "she freaked out and we never spoke again.”

** has reached out to Wilkinson's reps for comment.

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