Holly Madison Exposes the Surreal Secret Ceremony Hidden Behind Playboy Mansion Doors

If you’ve ever wondered what it was really like behind the infamous gates of the Playboy Mansion, buckle up—because Holly Madison’s revelations blow the glossy fantasy right out of the silky pajamas . Picture this: you think the most awkward part of sharing a house is arguing about Netflix passwords or whose turn it is to take out the trash, not orchestrating synchronized bedtime routines for one aging mogul’s amusement . So, what happens when every night is “ladies’ night”—and not in a good way? With a cocktail of dark humor and sobering reflection, Holly Madison cracks open the “bizarre rituals” and unspoken agreements that ruled her years living with Hugh Hefner—a universe as far from a fairytale as reality TV is from real life . If you ever thought sleeping in matching flannel PJs could be weird, wait until you find out what else was required . Yeah, this isn’t your grandma’s sleepover . Prepare for a peek down the rabbit hole that’s messy, surreal, and unfiltered—just like Holly’s memories . LEARN MORE

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.

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)

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’.

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.”

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)

“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.”