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Holly Madison revealed bizarre ritual she experienced whilst living with Hugh Hefner in the Playboy Mansion

Home> Entertainment> Celebrity

Updated 20:46 6 May 2025 GMT+1Published 20:43 6 May 2025 GMT+1

Holly Madison revealed bizarre ritual she experienced whilst living with Hugh Hefner in the Playboy Mansion

The former girlfriend detailed the 'bedtime routine' they hated

Jess Battison

Jess Battison

Holly Madison opened up about the bizarre rituals she experienced while living with Hugh Hefner.

The 45-year-old dated Hef in her late 20s from 2001 to 2008, shacking up in the notorious Playboy Mansion.

Over the years, and particularly since the editor-in-chief’s death in 2017, many former Bunnies, partners and girlfriends have spoken out about their time in the ‘dirty’ house.

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And while she now hosts the latest season of The Playboy Murders, she wrote in her 2015 book Down the Rabbit Hole about her time in with Hefner in the Mansion.

This includes her discussing the ‘bedtime ritual’ which the girlfriends in the house were expected to take part in.

“I didn't immediately realise that all girlfriends were required to sleep with Hef,” she wrote.

Holly Madison lived in the Playboy Mansion in the 00s (Raymond Hall/GC Images)
Holly Madison lived in the Playboy Mansion in the 00s (Raymond Hall/GC Images)

Madison said that while in a limo back with the girlfriends, one of them explained to her that all of them were ‘expected to join Hef in his bedroom’.

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She claimed that they ‘all hated’ this routine and would try and ‘get it over with as quickly as possible’.

She said this ritual before bedtime would happen biweekly as another girlfriend apparently advised her to just ‘fake the f**k’.

Madison added that they would all get dressed into identical flannel pyjamas before the ‘bedtime routine’ and on her first time there was ‘roughly a third of a bottle of vodka sloshing around in my stomach’.

And as the ritual played out around him, according to Madison, Hef would watch porn, smoke a joint of 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.”

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

Madison would partake in Hef's 'bedtime routine' (Michael Loccisano/FilmMagic)
Madison would partake in Hef's 'bedtime routine' (Michael Loccisano/FilmMagic)

“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.”

The morning after her ‘first bedroom experience’, she said she felt ‘damaged and affected’ but the shame in herself spurred her on to ask to move in.

“After disappointing myself like that, I had to come away with something positive, something to make it right in my mind, somehow,” Madison explained. “I knew that if I couldn’t find a silver lining, I couldn’t forgive myself for the night before.”

Featured Image Credit: J. Merritt/FilmMagic/Getty Images

Topics: Hugh Hefner, Celebrity News, 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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  • Hugh Hefner's ex-girlfriend Holly Madison slams 'disgusting' sex act she hated doing with Playboy owner
  • Former Playboy ‘Bunny’ shared horrific reality of living in mansion with Hugh Hefner
  • Former Playboy model living in £60 tent reveals truth behind living with Hugh Hefner in his mansion
  • Pamela Anderson revealed bizarre Hugh Hefner sex request that made her realise she 'needed to leave' Playboy Mansion

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