Rules Former Girlfriends Of Hugh Hefner Had To Follow

Before his death on September 27, 2017, Hugh Hefner was known for his larger-than-life persona as the head of the Playboy empire and the master of the Playboy Mansion. With a multitude of Playboy Bunnies on his arm at any one time, Hefner was regularly the focal point of attention, with onlookers curious about his seemingly hedonistic and unattainable lifestyle. However, the women living alongside Hefner in the Playboy Mansion were apparently subjected to a slew of rules, some minuscule and some extremely serious.

In her 2015 book "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," Hefner's ex, Holly Madison, wrote, "There were many rules to living in the mansion, but most of them I had to figure out on my own. Like I said, no one handed me 'The Playboy Mansion for Dummies' when I arrived." Learning these rules was apparently a rite of passage for any new girlfriend joining the Playboy ranks. 

But what exactly were the rules that Hugh Hefner's former girlfriends had to follow while living in the Playboy Mansion? Join us as we explore the wild rules allegedly instigated by the late Playboy mogul.

Living in the Playboy Mansion allegedly came with a slew of a strict rules, and that included a very early curfew. While Hugh Hefner and his many girlfriends were sometimes seen out on the town, when the women weren't partying with their boyfriend, they had to be at home on time. And by all accounts, that curfew was pretty serious. One of Hefner's former girlfriends, Izabella St. James, told Fox News Digital in July 2023, "We had to be home by 9 p.m." She added, "Hef didn't want girls to go out and party without him. I suppose he didn't want us to have the opportunity to be unfaithful."

In 2021, Jenna Bentley, another of Hefner's former girlfriends, opened up about her Playboy Mansion experience during an interview with Jam Press (via the Daily Mail), saying, "I mean, even though we had a 9 p.m. curfew it wasn't like we were prisoners." She continued, "Although if you missed curfew you were sleeping on the lawn. They were very strict about it."  

Clearly, Hefner had some pretty strict rules for those living with him, and disobedience had some major consequences, such as spending the entire night trying to get some shuteye in the garden.

It'll come as a surprise to literally no one that Hugh Hefner's girlfriends were allegedly expected to take part in group sex sessions with the media mogul every week. While recollections vary regarding what exactly happened during group sex at the Playboy Mansion, some of Hefner's exes have dared to open up about the unique experience. During a 2015 interview with BuzzFeed News, Holly Madison said of the group sex nights, "It was always Wednesdays and Fridays after the club." She continued, "It was always exactly the same because that's just how he likes to live his life." According to Madison, all of Hefner's girlfriends that resided at the Playboy Mansion were apparently expected to take part. "They knew it was kind of a quote-unquote requirement for living there, and expected," Madison told Buzzfeed News. "And it had kind of a chore vibe, I felt.

During an episode of A&E's "Secrets of Playboy," which aired in July 2023 (via USA Today), Zoe Gregory claimed that Hefner would take Viagra before having sex with all seven of the girlfriends he had at the time, spending approximately a minute with each of them. "But when you're doing that, a minute feels like five," she said on "Secrets of Playboy." During the same episode, Izabella St. James said, "Girls all shower or take a bath. And people sit on his bed. He would smoke a joint, and girls would pop champagne bottles and order food."

While Hugh Hefner's girlfriends got to live in the Playboy Mansion rent-free, they were also given a weekly allowance. However, receiving an allowance from Hefner wasn't as glamorous as it may initially sound. In her memoir "Bunny Tales: Behind Closed Doors at the Playboy Mansion," Izabella St. James got candid about how it really felt to take money from Hefner, writing (via the Mirror), "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." She continued, "We all hated this process."

According to St. James, the demeaning experience of collecting a weekly allowance only opened Hefner's girlfriends up to criticism from the magazine owner. "Hef would always use the occasion to bring up anything he wasn't happy about in the relationship," she wrote in her memoir. "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." 

If true, Hefner's girlfriends were completely beholden to the Playboy icon, as they appeared to totally rely on him financially and had no choice but to take his verbal critiques. Collecting an allowance was allegedly another challenging part of living in the Playboy Mansion.

You've likely noticed that all of Hugh Hefner's girlfriends look alike, particularly when it comes to the color of their tresses. And according to Hefner's exes, there's a reason that all of his partners have blonde hair. During an appearance on the "Power: Hugh Hefner" podcast in 2021, Holly Madison explained, "You were expected to look a certain way obviously, you had to have the blonde hair." As well as having matching hair, Hefner's girlfriends also had to place a focus on the way that they dressed. "You were given $1000 a week that was supposed to be a clothing allowance," Madison said. 

In her 2015 book "Down the Rabbit Hole," Madison also alleged that Hefner would be mean if he didn't like someone's haircut. After getting her long blonde hair cut into a cute bob, Madison was supposedly lambasted by Hefner, who allegedly told her, "You look old, hard, and cheap." While Madison had been happy with the new style, Hefner's words apparently haunted her for years afterwards, proving just how much control he seemingly had over his girlfriends. 

So if you wanted to live in the Playboy Mansion, that reportedly carried the caveat of making sure your hair was colored and styled to Hefner's specifications.

Since Hugh Hefner's death in September 2017, his ex-girlfriends have been less tight-lipped about their experiences with the Playboy owner, and that includes the use of non-disclosure agreements. In the celebrity world, the signing of NDAs is fairly common, but it seems that Hefner was pretty strict about making sure that all of the women in the Playboy Mansion had signed the contracts while dating him. During an interview with Jam Press (via the Daily Mail), Hefner's ex, Jenna Bentley, claimed, "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." She continued, "But I have seen a lot of celebrities have sex there and I've also participated in a lot of it."

When Holly Madison released her "Down the Rabbit Hole" memoir in 2015, Us Weekly suggested that she was able to be so candid as she hadn't signed a non-disclosure agreement while dating Hefner. However, Radar reported that Madison had, in fact, signed an NDA, meaning that she'd allegedly broken it by writing about her Playboy experiences in her book. 

Regardless of what the truth is, it seems that many of Hefner's exes have decided to break their NDAs following his death, in an attempt to share the truth of what really went on at the Playboy Mansion.

While Hugh Hefner usually had multiple girlfriends at any one time, his partners weren't afforded the same privilege. In fact, one of Hefner's strictest rules apparently involved his girlfriends remaining completely faithful to him, even while he was sleeping with several people. "While Hef could date an entire sorority house full of girls, we were to remain totally loyal," Holly Madison wrote in her book "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny." During her appearance on the "Power: Hugh Hefner" podcast, Madison elaborated, "You weren't allowed to date other guys, which I was fine with too, because I wasn't interested in dating at that point in my life."

Jenna Bentley also noted the strict "no boyfriends" rule during her interview with Jam Press (via the Daily Mail), revealing that "even meeting boys was an immediate kick-out." Basically, it would appear as though Hefner was pretty possessive when it came to his girlfriends, and although he was allowed to date multiple people at once, his partners were most definitely not.

Moving into the Playboy Mansion carried a plethora of rules with it, including everything from hair color to nighttime curfews. But moving into the Mansion also meant that girlfriends were expected to give up their previous places of residence. While appearing on the "Power: Hugh Hefner" podcast in 2021, Holly Madison explained, "You weren't allowed to have an apartment of your own, which while I lived there, there were some women who did, they just kept that a secret from him." While it was a rule that some girlfriends allegedly broke, it was certainly frowned upon to do so. 

Of course, there were positives to not having to worry about rent in Los Angeles, which is not cheap. In her memoir "Down the Rabbit Hole," Madison even opened up about the rags to riches experience she felt when moving into the Mansion, writing, "Whose life was I living? Private jets! Luxury hotels! Last month I was barely making rent on a s****y shared apartment." 

However, the fact that Hefner's girlfriends weren't allowed their own apartments outside of the Playboy Mansion seemingly suggests that they were bound to a very particular way of life while living there, for better or worse.

The 29-room Playboy Mansion, with its infamous grotto, likely had a lot of staff at any one time to look after Hugh Hefner, his girlfriends, and his friends. However, when it came to the Playboy Mansion's staff members, Hefner's girlfriends were allegedly warned to stay away. Former girlfriend Izabella St. James told Fox News Digital in June 2023, "There was no mingling with the staff. You weren't supposed to be hanging out with the butlers." Seemingly, Hefner preferred his girlfriends to keep themselves very separate from his employees.

Holly Madison also discussed the "no mingling with the staff" rule in her "Down the Rabbit Hole" book, writing, "The girls were not allowed to 'fraternize' with the staff unless absolutely necessary." She continued, "This rule was not to be taken lightly. Hef would totally lose it if he caught one of us talking with anybody on the service team." As for why Hefner was apparently so strict about this particular rule, Madison suggested that, according to rumor, his ex-wife allegedly slept with a staff member once, leading him to create the stipulation. 

While the truth may never be known, Hefner's girlfriends were apparently careful about who they became friends with while living in the Playboy Mansion as a result.

As if there weren't already enough rules implemented by Hugh Hefner in the Playboy Mansion, the late mogul's girlfriends were strictly banned from taking drugs, according to Holly Madison. In "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," Madison wrote, "The climate inside the mansion was toxic. I didn't participate in the cocaine benders, the side boyfriends, or all their harebrained moneymaking schemes that were all in direct violation of Hef's house rules." Later in the book she confirmed, "I'd been offered cocaine countless times since moving in — it was definitely the drug of choice in the mansion."

However, in A&E's "Secrets of Playboy," another one of Hefner's former girlfriends suggested that the magazine founder really did partake in some hard drugs from time to time. Per Buzzfeed News, ex-Playmate Sondra Theodore claimed on the series, "[Hefner] pretended he wasn't involved in any hard drug use at the mansion, but that was just a lie." She continued, "It was such a seduction, and the men knew this — that they could get girls to do just about anything they wanted if they gave them a quaalude." 

During "Secrets of Playboy," Madison also revealed that Hefner had allegedly offered her quaaludes when they first went out together, as reported by Insider. But whether or not Playmates were meant to be taking drugs under Hefner's watch is perhaps another story.

It may surprise some to find out that Hugh Hefner insisted on spending Christmas Day with all of his girlfriends at the Playboy Mansion. In her revealing "Down the Rabbit Hole" memoir, Holly Madison wrote, "I was surprised to find out that Christmases were always spent with Hef." If any of the women had family commitments to attend, they seemingly needed to make sure they were back at the Mansion for the holiday itself. "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," Madison explained.

It would appear as though Hefner was an excellent gift giver, as his girlfriends apparently looked forward to the holiday season — in spite of all the rules. "That was the one house rule that no one seemed to mind, because Christmas was when Hef was most generous with his girlfriends," Madison wrote. Hefner apparently gave his girlfriends a large budget to spend on gifts for one another, too, leading to some designer purchases, according to Madison. 

While there were undoubtedly difficult and even upsetting moments at the Playboy Mansion for some of Hefner's girlfriends, Christmas was seemingly a totally different story. As Madison explained, "Hef really is a big kid at heart — and he loves Christmas morning."

Just as Hugh Hefner allegedly disliked short hair and insisted that all of his girlfriends were blonde, he also reportedly hated red lipstick. In "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," Holly Madison wrote, "Among the many unspoken rules at the mansion, the red lipstick rule was one of the more notorious. Hef hated red lipstick." And in case anyone disbelieves this particular rule, Madison reiterated, "I'm not over-exaggerating here; Hef absolutely despised red lipstick and wouldn't allow his girlfriends to wear the color."

Madison even claimed to have experienced Hefner's wrath firsthand when she wore red lipstick following her ill-fated decision to cut her blonde hair short. After denouncing her new short hairstyle, Hefner allegedly told her, "Don't ever wear red lipstick again," proving just how serious he seemingly was about the rule. 

Unfortunately, living in the Playboy Mansion allegedly came with a whole host of rules, many of which seemed challenging, distressing, or arguably unacceptable. Luckily, the late Hugh Hefner's former girlfriends can now speak their truths and tell their stories in their own words.