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Playboy founder Hugh Hefner became a controversial figure when he was accused of subjecting girls to s*xual abuse and exploitation. Most recently, his life became a subject of scrutiny in the documentary,Secrets of Playboy. Hefner’s Playboy mansion was home to numerous women at a time, who were all considered Hefner’s girlfriends. Hefner also had several strict rules for these girlfriends.
For years, these girls were tight-lipped about the experiences inside the mansion, mainly due to the signing of NDAs with the company. However, with Hefner’s passing in 2017, more women spoke out against the questionable lifestyle of the mogul.
Playboy Founder Hugh Hefner Had Three Weird Rules For His Girlfriends
By the timeHugh Hefnersplit from his second wife Kimberley Conrad in 2010, he was already in a relationship with Playboy model Crystal Harris. While they got married in 2012, Hefner also had relationships with multiple womenwho lived in the Playboy mansion.
Out of Hefner’s young girlfriends,Holly Madisonis the most famous as she opened up about the problems she faced after she left the mansion in 2008. In her 2015 book,Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Madison revealed that there were many rules she had to follow to live in the mansion.
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One rule the late Playboy founder had was a group s*x with all the girls living at the mansion. Madison shared withBuzzfeed Newsthat it was a“quote-unquote requirement”for living in the mansion. She shared that the act took place every Wednesday and Friday after the club. She added,“It was always exactly the same because that’s just how he likes to live his life.”
There was also a strict curfew for the girls who lived in the mansion. According to Izabella St. James, the girls had to be home by 9 p.m. She shared withFox News Digital,“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.”Breaking the curfew had consequences, as Jenna Bentley revealed toDaily Mailthat they were made to sleep on the lawn for missing curfews.
The third strict rule was a weekly allowance that the girls had to collect on Fridays. St. James revealed in her memoir,Bunny Tales: Behind Closed Doors at the Playboy Mansion, that Hugh Hefner had a demeaning process of giving the allowance. St. James wrote (via 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. We all hated this process.”
Hefner would use the allowance-giving process to share criticisms about his girlfriends. According to St. James, the complaints were about the lack of harmony among the girlfriends or their lack of participation in his group s*x parties.
Holly Madison Knew About What She Would Have To Do In The Playboy Mansion
For years, fans believed that Holly Madison and the other girls had a celebrity-like life in the Playboy mansion. However, it was far from the truth. Madison opened up about her time in Hugh Hefner’s mansion when she appeared on theCall Her Daddypodcast. She revealed that entering the mansion meant thatthey would have to sleep with Hefnerand risk being called a sl*t.
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However, Madison revealed that she had little choice at the time. She was desperate and was living on someone else’s couch. Madison complied with Hefner’s conditions just so that she could pay her bills without worrying about becoming homeless. Madison shared with theCall Her Daddy podcast:
“The only reason I even had the balls to do that was because I was kind of desperate. I was sleeping on somebody’s couch, and I just felt like I need a minute to reset my life. And I felt like I could stay at the mansion and have a minute to not worry about bills.”
Hefner died at the age of 91 in 2017 and became a controversial figure well after his passing. Hefner and his girlfriends were featured in the reality series,The Girls Next Door, which is now available for streaming on Fubo.
Hashim Asraff
Senior Writer
Articles Published :3019
Hashim Asraff is a Senior Entertainment Writer at FandomWire, with over 2,800 articles published on celebrity culture, comic book movies, and major TV franchises. With a background in Sociology and a keen interest in pop culture, Hashim brings a unique lens to breaking news stories, character deep-dives, film rankings, and fan-driven perspectives.His coverage often includes the MCU, DCU, hit network shows, and celebrity profiles, giving readers a rich blend of entertainment and analysis. A longtime fan of crime and investigative series, Hashim has watched thousands of episodes of NCIS, Criminal Minds, Law & Order: SVU, Bones, Blue Bloods, and The RookieA passionate storyteller and wordsmith, Hashim has also worked as a ghostwriter and managed multiple social media handles. He brought his writing expertise to FandomWire to also pursue his lifelong love for cinema and television.
