Hugh Hefner’s former girlfriend and ex-Playboy Bunny Holly Madison has shared new details about the small “black book” she says was used to log information about the women in the Playboy Mansion.
Madison, who dated Hefner from 2001 to 2008, has spoken publicly for years about what life was like while she lived at the Mansion.
During that time, she was known as Hefner’s “number one” girlfriend—his preferred partner in the household, even though he was simultaneously dating other women.
Over the years, Madison has discussed a range of topics people have long speculated about: strict house rules, the state of the property, group sex nights, and the record-keeping she says left her feeling unsettled.
One item she has repeatedly mentioned is the “black book,” which she alleges contained private notes and tracking information. Madison has said that when she finally moved out, she wished she could have destroyed it.
Since Hefner died in 2017 at 91, the alleged contents of the book have been discussed in multiple places, including A&E’s Secrets of Playboy.
Madison has also revisited the subject on her Girls Next Level podcast, which she co-hosts with another former girlfriend, Bridget Marquardt.
In one episode, Marquardt said Hefner kept a journal-like book that went beyond casual notes—and, she claimed, included a running account of sexual encounters.
“The black book kept track of a few different things,” she explained. “It kept track of when somebody collected their allowance. He would mark it off so you couldn’t ask for it twice. It also kept track of who slept with him and when.”
They also alleged they’d heard from other women in the house that Hefner used the same book to comment on girlfriends and their “performance” in the relationship.
“He’d be like, ‘Oh, you’ve been on your period for three weeks,'” the pair recalled.
Madison has said the existence of the book was one of the reasons she felt uneasy, and that she desperately wanted it gone when she left.
She recalled: “When I was moving out of the house – I wanted [to] so badly, but I had no access – if I could have gotten to the drawer and burned that book, I would have.”
She explained: “Because I’m just so disgusted with how he keeps a record of who he has sex with each night and takes all these nudes of all the girls when they’re in the limo and drunk and flashing, and then prints them out, hands them to every girl in the limo, puts them in a scrapbook.”
Madison went on to claim: “So, that was another thing that made me feel weird and afraid to leave, I feel like there was this mountain of revenge porn that everybody is going to see at some point, so I might as well hide here – it was just gross.”
The “black book” and the wider allowance system have also been criticized by other former girlfriends.
In her 2006 memoir Bunny Tales: Behind Closed Doors at the Playboy Mansion, Izabella St. James described a routine she said was humiliating, alleging that collecting their allowance involved awkward waits while Hefner dealt with messes in his room.
St. James wrote: “We had to go to Hef’s room, wait while he picked up all the dog poo off the carpet – and then ask for our allowance.
“We all hated this process.”
She also claimed the weekly allowance conversation could turn into a moment where he raised grievances.
“Hef would always use the occasion to bring up anything he wasn’t happy about in the relationship,” she wrote. “Most of the complaints were about the lack of harmony among the girlfriends – or your lack of sexual participation in the ‘parties’ he held in his bedroom.”
St. James also claimed: “If we’d been out of town for any reason and missed one of the official ‘going out’ nights he wouldn’t want to give us the allowance. He used it as a weapon.”
Hefner was married three times and dated multiple girlfriends. Madison, Marquardt, and Kendra Wilkinson became especially well-known through their reality series Girls Next Door.
In addition, several former Playboy figures have spoken about intimacy with Hefner and what some say happened behind closed doors.
Madison previously discussed the contrast between private sex and group settings while speaking on the In Your Dreams podcast.
She said: “If it was just me and him, it was a lot more normal than you would think.
“It’s a very different story between when we were just by ourselves than with everybody else in the room.
“Everybody else in the room, no. That was disgusting.
“I hated it. I made it very known I hated it.”
In her 2024 biography Only Say Good Things: Surviving Playboy and Finding Myself, Hefner’s third wife Crystal also wrote about what she described as the routine nature of sex in their relationship, including her description of “blue little pill nights.”
She additionally claimed she played the same Madonna song each time so that “no other music [would] be contaminated by this place.”
Elsewhere in her book, Crystal characterized their sex life as repetitive, writing: “This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time.
“Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pajamas. The dimming of the lights. The music. The porn. Passing the pot. And then the sex.”
She described it as though Hefner ‘was just going through the motions of something that had once been fun and sexy’.
Crystal added: “Or maybe it was never fun and sexy.”
Madison has also written about early expectations versus reality when she moved into the Mansion and was told to wear pajamas, reflecting on how little the public fantasy matched what she experienced.
She wrote: “When I think about it now, it’s almost comical. Every red-blooded American male has no doubt fantasized about what went on in Hugh Hefner’s bedroom with his harem of blond bombshells. The answer? Not a whole lot.”
She added: “My turn was over just as quickly as it had started.”
Another former girlfriend, Sondra Theodore—who dated Hefner between 1976 and 1981—also addressed her experience on A&E’s Secrets of Playboy.
She said: “He scared me a lot at the end because you couldn’t satisfy him — he had to have more and more and more,” Theodore recalled.
“I might as well have been a vibrator, I might as well have been a sex toy — because that’s what it was. And nobody knew the hell I was in.”
Twins Karina and Karissa Shannon also recounted their own story for the same docuseries, alleging their 19th birthday took a disturbing turn after they were invited to Hefner’s bedroom.
During the interview, Karissa claimed they were given a pill that left them “the most inebriated we’ve ever been,” before they say they had sex with Hefner, who was 86 at the time.
“We had never done a threesome together before, we would never want to,” Karina said.
Karissa added: “And that was our 19th birthday. You’re never going to forget that. He didn’t even finish. Just imagine this, just his old hand kind of shakes [as he’s] touching your boob.
“It’s like you’re having sex with your grandpa. And he laid there, looking up, and he was like, ‘My babies, my babies. You love me.’”
Karissa continued: “We ran down the hall to the spare bedroom we were staying in. We hit the shower, steaming hot. Our skin was red from just trying to, like, sterilize.”