Weird Rules Women Living At The Playboy Mansion Had To Follow

The late Hugh Hefner is one of the most notorious men in pop culture history. A writer-turned-editor-in-chief, Hefner gained notoriety for founding Playboy, one of the most prominent publications featuring photos of nude women. In 1971, Hefner shaped pop culture history once again when he purchased a property in Holmby Hills, a luxurious enclave of Los Angeles nestled between Beverly Hills and Bel Air. The home and surrounding amenities would go on to be called the Playboy Mansion.

The Playboy Mansion became a cultural touchstone. Hefner used it as a venue for lavish parties and other unofficial Playboy business. He also used it as a dormitory of sorts, providing a place to live for beautiful women either vying for his love or hoping to be put in the magazine. According to the women who stayed there, life at the Playboy Mansion was either a dream, a nightmare, or some combination of the two. No matter the women's perspectives on their time there, they can all attest that there were strict rules they had to follow as denizens of one of Los Angeles' most infamous estates. Here are the weird rules women living at the Playboy Mansion had to follow.

Of all the rules that the women living at the Playboy Mansion had to follow, perhaps the most notorious was the curfew. Hugh Hefner, longtime resident and owner of the Playboy Mansion, required that the women living under his roof be home every evening by 9 p.m. The curfew was no secret — women who dated Hugh for years, like Holly Madison and Bridget Marquardt, knew about the curfew before moving into the Mansion, and it was mentioned several times throughout the E! reality series "The Girls Next Door." Although Hugh never gave much of a reason for the curfew, some women have shared the consequences of missing it, most citing receiving a reprimand from Hugh.

While 9 p.m. seems quite early, for some women, the curfew was even earlier. On an episode of the "Beneath the Surface" podcast, Crystal Hefner and her stepson Marston Hefner talked about her arrangement. "I feel like I was very restricted," she said. "I think a lot of it was very hard for me, because by the time your dad got older, he didn't want me out past 6:00 p.m., so I was home before dark most days."

Hugh Hefner was a man with control and influence, and as many of his former girlfriends have stated, he used that control and influence to ensure the women living in his home met a certain standard of appearance. One particular look he didn't like was red lipstick. Looking back on her life at the Playboy Mansion, Holly Madison shared on the "Ahead of the Curve" podcast that she believed Hefner's distaste for the lipstick shade came from its use on models in the 1950s. According to Madison, Hefner associated red lipstick with more mature women; the former editor-in-chief wanted the women he dated and put in Playboy to have a younger look.

Hefner didn't just dislike red lipstick — he would even reprimand certain girlfriends for wearing it. As Hefner's ex-girlfriend Bridget Marquardt shared in the A&E docuseries "Secrets of Playboy," "[Holly] came down with red lipstick one time, and he flipped out and said he hated red lipstick on girls [and to] take it off right away, even though other people could wear red lipstick, and it didn't seem to bother him." Madison has said that she believes Hefner didn't allow her to wear red lipstick as a means of control; while it was allowed at the beginning of their relationship, the longer she dated Hefner, the stricter the rule became.

Hugh Hefner was known for his role in the sexual revolution in the middle of the 20th century. He started a magazine for which women posed nude, and for years of his life, he very publicly dated multiple women at the same time. Hefner's persona naturally led people to wonder whether the women he was dating were having sex with him. As many of his girlfriends have shared, they did. Each woman who's shared her sexual experiences with Hefner has told a slightly different story, but the stories have had some similarities. Sex toys, group sex, schedules, and routines were all part of intimacy with Hefner, especially as he aged. Some women have mentioned drugs being part of intimacy with him, too.

Several women who dated Hefner have noted their own mental state while engaging with him sexually. As Hefner's ex-girlfriend Kendra Wilkinson said on the series "I'm A Celebrity...Get Me Out of Here!" (via the Mirror), "I was usually very very drunk doing those evenings, I tended not to care about much until the next day. I had to be very drunk or smoke l lots of weed to survive those nights." Wilkinson also stated on the series that she was never forced to have sex with Hefner, however, many women he's dated have said they felt it was expected.

When picturing a woman Hugh Hefner either dated or put in Playboy, a blonde woman likely comes to mind. That's no coincidence — Hugh preferred flaxen-haired ladies, and most of the women he associated with kept their hair the lightest shade it could be. Some even did so to their detriment. As Hugh's third wife, Crystal Hefner, said to People, "​​So I'd have to go bleach it and it would burn my scalp and I'd have blisters. But for some reason I thought this was all normal and that's what it meant to be seen as beautiful in Hef's eyes." 

Hugh apparently preferred long hair, too. As Hugh's ex-girlfriend Holly Madison shared on the A&E docuseries "Secrets of Playboy," she learned that the hard way. Early in their relationship, Madison cut her hair, and the new look was not well-received. "He flipped out on me. He was screaming at me and said it made me look old, hard, and cheap," she said of Hugh.

As other women Hugh dated have attested, although Hugh expected his girlfriends to maintain blonde locks, he did provide the funds needed for the look. As Madison shared in her memoir "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," Hugh had an account at the José Eber Salon, and the women who lived at the Playboy Mansion were allowed to make appointments as they pleased.

Hugh Hefner liked having lots of women in his presence. While there were many years of his life spent in committed monogamous relationships, he was more famous for dating multiple women at once. The famed magazine editor had as many as seven girlfriends at one time, each of them living at the Playboy Mansion. While Hefner was allowed to date as many women as he wanted, the girls with whom he was in relationships were not allowed to have extraneous relationships. Hefner's ex-girlfriends Izabella St. James and Zoe Gregory delved into this in the docuseries "Secrets of Playboy."

Not all of the women accepted the rule that they weren't allowed to date other men, and according to Hefner's ex-girlfriend Holly Madison, several of his other ex-girlfriends didn't follow it. As she shared in an episode of "Call Her Daddy," "When I first moved in, there were six other women living there, and a lot of them were dating other people on the side. They weren't supposed to. That was against the rule and Hef was super jealous." According to Madison, the women who were dating men outside of the Mansion would lie to Hefner about their whereabouts to maintain their other relationships.

Interestingly, at least one of Hefner's girlfriends was married when she lived at the Mansion. In 2007, Bridget Marquardt told Star that she was still technically married to another man when she moved into Hef's place, but she was working on getting divorced. Perhaps surprisingly, Hef was okay with it.

Dating Hugh Hefner was a full-time job, and the women were compensated for it. Hefner made a lot of money through his work as founder and editor-in-chief of Playboy, and he spent a lot of it, especially as he aged, on his girlfriends. Still, the women who lived at the Mansion were only allowed to spend so much. As ex-girlfriends have stated and he has confirmed, Hefner gave each of his girlfriends $1,000 in cash each week. "That part is true. If you write it and make it sound sleazy, that's easy to do. But the girls got a clothing allowance," Hefner told the Daily Beast.

While Hugh Hefner's girlfriends' weekly allowance might seem like payment for intimacy, not all of the women felt that way. As Bridget Marquardt said in a 2022 episode of her podcast with fellow ex-girlfriend Holly Madison, "Girls Next Level," "I never looked at the allowance that we got or anything like that as, like, money for sex. It was money for the clothes that we needed to get, money for not working." Madison went on to add that the women he dated were expected to attend events with Hefner and be available whenever he wanted.

NDAs, or non-disclosure agreements, are commonplace in Hollywood. According to some women who lived at the Playboy Mansion, they were commonplace there, too. Per The U.S. Sun, former playmate Jenna Bentley, who lived in another home owned by Hugh Hefner often referred to as the Bunny House, told Jam Press, "I had to sign a very, very, very iron-clad NDA, which is why I can't talk about who had sex at the mansion." It's also been reported that Hugh's ex-girlfriend Holly Madison had to sign one, too, although she has denied this allegation.

Though she had a long relationship with Hugh Hefner too, Crystal Hefner has said that she was never made to sign an NDA either. However, she has said Hugh requested that, after his death, his widow would only speak positively about her relationship and time at the Mansion. "'Only say good things.' I was good at that, I had promised. For a long time, I kept that promise, but that promise was killing me," Crystal said in her memoir, "Only Say Good Things: Surviving Playboy and Finding Myself." 

Nail art is a great way to show personality, but at the Playboy Mansion, it wasn't allowed. As Hugh Hefner's widow told People, the Playboy editor-in-chief was very strict about the appearance of the women he lived with, right down to their nails. "Our nail polish couldn't be anything but some neutral color, no French manicure," Crystal Hefner said. She added that Hugh also forbade her from wearing a belly button ring and that he insisted she wear the Playboy logo as much as possible.

Part of living at the Playboy Mansion meant attending lavish parties, and the women were expected to present a certain way for those, too. As Hugh's ex-girlfriend Holly Madison noted, getting ready to attend a Mansion event was an all-day affair, one that ensured every detail of Hugh's girlfriends looked as perfect as possible. "Preparing took an entire day. In the morning, we would go to the salon to get our hair colored, get a deep-conditioning treatment, blowout, and style. Then nails, hair, tan, spend an hour or so on makeup, and before you knew it the whole day would be gone," Madison told Allure in 2015.

Parties at the Playboy Mansion were some of the most infamous events in Hollywood for decades. From rumors of orgies and heavy drug use to evidence of nearly-naked women and the ultra-rich and famous in attendance, Playboy Mansion party lore is deep and intriguing. As Hugh Hefner's ex-girlfriend Bridget Marquardt shared on an episode of "Call Her Daddy," in the early 2000s, an invitation to the Playboy Mansion was coveted by pretty much everyone in Los Angeles. And as fellow ex-girlfriend Holly Madison said, attendees weren't allowed to bring cameras to the parties, making the experience especially desirable for celebrities as they felt free to behave as they pleased.

Mansion parties weren't all they were cracked up to be for the women who lived there, though. As Madison said in her 2015 interview with Allure, although she did enjoy the events, there were drawbacks as one of Hefner's girlfriends. "[Parties] weren't crazy like you might expect. We would be expected to sit with Hef at his table for the entire time. It was heavily discouraged sneaking off on your own to socialize," she said.

Holidays were important to Hugh Hefner, and he insisted that his girlfriends be by his side on those days. As Hefner's ex-girlfriend Holly Madison said in her book "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," "Christmases were always spent with Hef. Girlfriends were given 'off' days before or after the holiday to visit family and friends, but there were no exceptions for the actual day itself." Other holidays were important to Hefner, too. The editor-in-chief always threw a lavish Halloween party, an Easter egg hunt, and a Fourth of July party.

Although they were expected to spend holidays with Hefner, there were perks. The Mansion was always decorated to the nines, especially at Christmastime, and the women living with Hefner received beautiful gifts. As Madison described in an episode of her and fellow ex-girlfriend Bridget Marquardt's podcast "Girls Next Level," the first Christmas she spent at the Mansion, she received cash from Hefner as a gift, and she was given money to buy gifts for each of the women living there. Louis Vuitton bags and Gucci shoes were among the gifts the gals received.

Living in the Playboy Mansion essentially meant you looked a certain way, and that was by design. "There were very specific rules about face, hair, makeup, body, clothes. And because this was Hugh Hefner's America, this meant being the blondest and the skinniest," Crystal Hefner said in her memoir "Only Say Good Things: Surviving Playboy and Finding Myself." Hugh liked certain features, and he wanted the women he lived with to have them. Crystal shared in her memoir that while she was always technically given a choice while living at the Playboy Mansion to conform to Hugh's beauty standards, she felt like she didn't have a choice the longer she lived there.

The women living with Hugh went to great lengths to meet his expectations, and he was willing to front the cost. "Hugh would pay if someone wanted [plastic surgery], so there was almost always someone in the house in recovery," Hugh's ex-girlfriend Holly Madison said in Allure.

Hugh Hefner was a scheduled man, and he expected his girlfriends to follow suit. While the women who lived with Hefner were allowed to do what they wanted (to a certain extent) during the day, they had to be present for his nightly events. Hefner's ex-girlfriend Holly Madison described the weekly schedule in her book "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny." Monday was called "Manly Night," Tuesday was called "Family Night," Wednesday and Friday were club nights, Saturday was a night in, and Sunday was the weekly pool party called "Fun in the Sun." The women had Thursday nights to themselves, as well as Monday and Tuesday nights as Hefner spent that time with his male friends and children.

The women living with Hefner also had a schedule in the bedroom. Those who were intimate with Hefner were expected to have relations a couple of times a week on Wednesday and Friday after they returned from the club. The women then followed a routine that involved taking a shower, getting into pajamas, and getting into Hefner's bed. For some, the routine included taking drugs and showering again afterward.

For many women, living at the Playboy Mansion was a placeholder until they were able to find success outside its walls. However, that was difficult for many of the famous home's residents as one of Hugh Hefner's rules was that the women couldn't work.

As Hefner's ex-girlfriend Holly Madison shared, not being able to work outside the Mansion led her to feel stuck. "So there were a few factors that over time made me afraid to leave the Mansion. Isolation was one of them, not feeling like I had friends outside the Mansion, not being able to work," Madison said on her podcast "Girls Next Level" in 2022. Madison went on to say that while she kept her job at Hooters when she initially moved into the Mansion, she later was told by Hefner that she needed to quit for multiple reasons, including his jealousy of her work. Madison was eventually able to work as an intern at Playboy Studio West, but this was years into her relationship with Hefner and several seasons into the series "The Girls Next Door."