By Chrissy Stockton Updated June 3, 2021

Like every other young women in the mid ’00s I was obsessed with the Girls Next Door. Holly, Bridget, and Kendra (Hugh Hefner’s current live-in girlfriends at the Playboy Mansion) were living a dream life — living with their best friends in a Beverly Hills Mansion where their days consisted of shopping for outfits for Playboy parties and playing with their dogs. But it wasn’t long until I got curious about what was behind the facade.

Did they seriously have sex with Hef? Did they even like him? How?

Doing a bit of research I found Izabella St. James’ tell-all of her time at the mansion. She described bizarre ritual sex (all the “girlfriends” in a circle around Hef who was watching porn on big screens and having sex with his “main” girlfriend while the others stimulated oral sex on each other and prayed for the nights to end quickly). It was dark and fascinating. When I heard Holly Madison was dropping her own tell-all, I knew she’d be forced to confirm or deny what Izabella said — but some of the secrets she revealed were even juicier. I ended up reading the entire book in one sitting. If you’re at all curious about what unfolds behind the scenes at Playboy, on any reality TV show, or with Holly, Bridget, and Kendra in particular you’ll want to do the same. Here are just a few of the bombs Holly drops.

The Rules

— Everyone at the mansion adhered to a rigid weekly schedule because Hef, like all old people, is obsessed with routine. The schedule was:

Fun-In-The-Sun Sundays — A pool party and screening a new release in the Mansion movie theater
Manly-Night Mondays — Hef’s friends came over for dinner and cards
Family-Night Tuesdays — Hef’s ex-wife and sons came over
Club-Night Wednesdays — Clubbing and the coming home for Hef’s bizarre sex ritual
Off-Night Thursdays — No planned activities
Club-Night Fridays — A repeat of Wednesday’s activities
Movie-Night Saturdays — A buffet dinner and a screening of an old movie in the Mansion theater

— The girlfriends, especially when Hef kept 7 girlfriends at a time, hated all of these activities. They were never free to do what they wanted. Even when they were at a club they were expected to sit with Hef or dance immediately in front of his table. They weren’t allowed to talk to other men.

— On nights were there were no scheduled activities, there was a 9pm curfew for the girls. On one occasion Holly witnessed two girls coming in 30 minutes late. Hef fake cried. And then threatened to kick them out of the house.

— Girlfriends were given a $1,000 weekly “clothing allowance” and allowed to use the house account at Jose Eber Salon in Beverly Hills. Saving the allowance or even using it for student loans was discouraged.

— “Side boyfriends” were not allowed — though almost all the girlfriends had one. Holly says that she’s only sure she and Bridget Marquardt followed the rule faithfully.

— Hef’s girlfriends are not to speak while he is being interviewed.

— Hef wanted his girlfriends to be seen driving nice cars around town to enhance the Playboy brand — but he didn’t want to give them the independence of owning an expensive vehicle. So, each girlfriend was a leased a car that was paid for by Hef as long as she stayed at the Mansion. This is one of many ways he exerted control over the girls — if she left the Mansion the girls knew they would not be able to afford the expensive leases on their own.

The Sex

— Yes, the girls all have sex with Hef.

— Yes, Hef takes a lot of Viagra. He carries it around in a crumpled Kleenex because he is old af. The Shannon twins think Hef is losing his hearing from taking it.

— In every room in the Mansion Hef keeps a tray with baby oil, Vaseline, and Kleenex. Many of Hef’s girlfriends get yeast infections from the baby oil.

— Holly estimates that “the majority” of playmates have had sex with Hef.

— Holly insinuates that Kendra is lying in her book Sliding into Home, when she describes being invited to the mansion and to be Hef’s girlfriend before she ever had sex with him. Holly says sex was used as initiation, and Kendra wouldn’t have been invited to the mansion or to be a girlfriend without doing it first.

— So many of Hef’s girlfriends were also involved with escorting and prostitution that he eventually demanded to see everyone’s passports and kicked everyone out who had been to Turkey recently (a hub of escort clients). There’s a theory that famed Hollywood madam Michelle Braun had planted one of her girls among the girlfriends to recruit girlfriends and playmates for her escort service. Holly believes this is true and that she knows who the girlfriend is.

The Other Girls

— Holly describes Hef as the ultimate mean girl who was like “a spoiled kid trapped in the body of an old man.” He pitted the girls against each other, loving the constant drama that made him feel fought over and desired.

— The role of “main girlfriend” seems prestigious and sought after, but most girls actually don’t want the extra work and lack of privacy (sharing a bedroom with Hef vs. having your own) that come with it. The main girlfriend doesn’t get any more allowance or gifts or other perks.

— While Holly and Bridget quickly became genuine BFFs, Holly didn’t like Kendra who she describes as ditzy and fake. Holly says “she seemed to have fried her brain somewhere over the course of her life” though they got along well during the years they were filming Girls Next Door.

— Holly’s first bedroom at the mansion shared a bathroom with another girlfriend. This girlfriend loved using laxatives and because the walls were thin, Holly often had to listen in on her bathroom sessions.

— Defending her reasoning for dishing the dirt by writing a tell-all, Holly says, “I always thought it would be classy not to kiss and tell… but after awhile you just get sick of having other people trying to tell your story for you.”

— Many of the girls felt trapped in the Mansion. “Everyone thinks that infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in.”

— When Holly broke it off with Hef, he “left” his will on her bed, showing her that if she stayed she would stand to inherit $3,000,000 — if she lived in the Mansion at that time.

The Mansion

— Holly was first invited to the Playboy Mansion for a party by Hef’s private doctor who saw her at a party she was working at as a Hawaiian Tropic model.

— As a struggling actor/model and full-time Hooter’s waitress with credit card debt from her breast enhancement plastic surgery, Holly found herself with nowhere to go. She asked Hef if she could move into the mansion. He replied, “You can stay for a while and we’ll see how it works out.”

— The Playboy Mansion kitchen cooks whatever food the girlfriends want, 24 hours a day. This policy used to be open to guests as well and Jack Nicholson would frequently call and ask for a cheeseburger, drive up to the mansion and have it delivered to his car — and drive off without even saying hello.

— Hef doesn’t know how to use a DVR. He has staff that records anything he highlights in TV Guide.

— While the Mansion used to be famous and invites to Mansion parties were hot commodities, A-list celebrities don’t make it out as much anymore. Because the Playboy business is suffering, they allow people to buy tickets and it’s no longer exclusive.

— Holly says that though the house and grounds look glamorous on the outside, they are dilapidated (and sometimes downright disgusting) on the inside. From carpets stained with the urine of the girlfriends ill-cared for dogs to the porn-chic decor like these naked lady knobs in Hef’s personal bathroom.

The Reality Show

— When they began filming Girls Next Door Holly, Bridget, and Kendra were okay doing things like changing with cameras present because they knew they’d have to be blurred out to be shown on TV. What they didn’t know at the time was that the cameras were trying to capture as much nudity as possible to sell in foreign markets were TV nudity was allowed.

— The girls were paid exactly $0 for the show’s first season. When the girls shot for the magazine, they were paid the very bottom price Playboy paid.

— As everyone suspects they would have meetings before each season to “decide” what the plot lines were going to be. Later when Holly had her own show, Jayde Nicole was brought in as a “character.”

— One thing Holly, Bridget, and Kendra had in common was that they all came from working-class backgrounds. They didn’t get along much of the time (especially Kendra vs. the other two) but one thing they could bond over was sight-seeing since none of them were well-traveled. Many of the bonds you see on the show felt real to them, at least for that time.

— Shortly after she began filming Girls Next Door Holly was prescribed Effexor, a drug used to treat depression.

— While nothing was said on camera, Holly had moved out of Hef’s room and was staying in one of the spare Mansion bedrooms while filming the last episodes of Girls Next Door season 5. The season followed Kendra and Bridget leaving and starting their new lives but nothing was said about Holly, though she’d already broken it off with Hef.

— Holly shares a delicious Mean Girls story about Barbara Walters. When the girls and Hef were on The View the producers arranged the set so that Hef was sitting in a chair with the girls awkwardly sitting around him. Once the cameras were on Barbara called them out, as if it was their idea to not have chairs of their own.

Despite whatever her time in the Playboy mansion cost her emotionally, Holly is now making millions of dollars a year, headlined her show on the Vegas strip and has a career she loves, and is happily married with a daughter and a dream house of her own. Read the rest of her confessions in her tell-all, Down The Rabit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.