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Hugh Hefner's ex reveals what happened during 'really weird' group nights in Playboy's bedroom
Home>Entertainment>Celebrity
Published 10:04 10 May 2026 GMT+1

Hugh Hefner's ex reveals what happened during 'really weird' group nights in Playboy's bedroom

Holly Madison claims all the women 'hated' doing the 'bedtime ritual' with Hef

Jess Battison

Jess Battison

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Once this illustrious place we saw filled with celebrities at glamorous parties and snapped in photo shoots, some of the ‘wonder’ of the Playboy Mansion has been dismantled over the years.

Particularly since Hugh Hefner’s death in 2017, a number of former Bunnies, partners and girlfriends have spoken out about what life was really like in the ‘dirty’ house.

That includes Holly Madison, who dated the editor-in-chief during her late 20s from 2001 to 2008.

She opened up about her time with Hef in her 2015 book Down the Rabbit Hole as well as during a recent appearance on Kristin Cavallari’s podcast Let’s Be Honest.

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The 46-year-old explained that when the Playboy boss would invite other women to join them in the bedroom, it turned into a ‘really weird scene’.

Holly moved into the Playboy Mansion when she was 21. (Denise Truscello/WireImage)
Holly moved into the Playboy Mansion when she was 21. (Denise Truscello/WireImage)

“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,” Madison recalled.

She claimed that ‘nobody liked it and everybody just tried to get it done as fast as possible’.

“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**t with each other,” the reality TV star added.

In her book, she further discussed the ‘bedtime ritual’ that the girlfriends in the Mansion were all apparently expected to take part in – something they ‘all hated’.

Madison said this would happen biweekly as one of the other girlfriends apparently advised her to just ‘fake the f**k’.

The women would apparently all get dressed into identical flannel pyjamas and on her first time, there was ‘roughly a third of a bottle of vodka sloshing around in my stomach’.

Madison went on to star in her own reality series. (Denise Truscello/Getty Images for Grant A Gift for Autism)
Madison went on to star in her own reality series. (Denise Truscello/Getty Images for Grant A Gift for Autism)

As it all played out around him, Madison wrote that Hef would watch porn, smoke weed and w**k while the women in the room ‘pretended’ to get off and ‘put on a show’.

“No one,” she wrote. “Was actually in the mood (besides Hef, I assumed) or turned on in the slightest. Like the porn itself, it was all just for show.”

She recalled on her first time that her ‘turn was over just as quickly as it started’.

“I have never had a more disconnected experience,” Madison said in her memoir. “There was zero intimacy involved. No kissing, nothing. It was so brief that I can’t even recall what it felt like beyond having a heavy body on top of mine.”

Featured Image Credit: Enos Solomon/FilmMagi

Topics: Hugh Hefner, Celebrity, Playboy

Jess Battison
Jess Battison

Jess is a Senior Journalist with a love of all things pop culture. Her main interests include asking everyone in the office what they're having for tea, waiting for a new series of The Traitors and losing her voice at a Beyoncé concert. She graduated with a first in Journalism from City, University of London in 2021.

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@jessbattison_

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