1. The sex testPlayboy is famed for its depiction of, as Hefner put it, “the romantic connection between the sexes”, and any woman who wanted to become a girlfriend had to bed Hefner first. If it went well, he might ask her to be a girlfriend.
2. Clothing allowanceHefner’s girlfriends weren’t allowed to have jobs so he provided them with a clothing allowance to ensure that they always looked their best. They were given $1,000 every Friday from their man, and he paid for any beauty (or cosmetic) treatments they asked for too.
“We had to go to Hef’s room,” former girlfriend Izabella St. James revealed, “wait while he picked up all the dog poo off the carpet — and then ask for our allowance. “We all hated this process. Hef would always use the occasion to bring up anything he wasn’t happy about in the relationship. “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. “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.”
3. Silence was goldenThe girlfriends were eye candy and nothing more. When Hefner took his girls to a red carpet event, they were expected to smile and look pretty, but not talk unless it was absolutely necessary. As far as Hefner was concerned, all attention should be on him.
“If you do something wrong, you’ll get an email,” Playboy model Melissa Howe revealed to The Mirror. “There’s a strict code of conduct. There are even rules about Instagram and Twitter. “You’ve got to show everything in a good light and if you’re drunk in a picture you’ll be in trouble.”
4. The ‘Number One Girlfriend’Not all of Hefner’s girlfriends were equal. He might have dated multiple women at once, but he always had a ‘Number One Girlfriend’ who he would have a more serious relationship with. She would share his bedroom, and amongst other duties, would be expected to have anal sex with him. Hefner’s longest standing number one girlfriend was Holly Madison. The two had a seven-year relationship, and she openly expressed a desire to marry the Playboy founder and have his children, despite their colossal age difference, but the relationship ended when he refused to put a ring on her finger. This prompted Madison to write an explosive tell-all book… In 2015, after years of relative silence about her relationship with Hefner, Madison wrote, Down the Rabbit Hole, where she portrayed the Playboy founder as a master manipulator. Things apparently got so bad for Madison that she contemplated suicide in the mansion.
5. The 9pm curfewThere might have been a lot of parties inside the Playboy mansion, but life for the girlfriends wasn’t one constant party, and they did not have a lot of freedom. In fact, they had a 9pm curfew. If they broke it, they risked being dumped by Hefner.
“When you’re here you have to be in by the 9pm curfew,” Howe added. “You’re not allowed to invite any friends up to see you.“You’re definitely not allowed male visitors. If you break the rules you get banned. Once you’re out, you’re out, you can’t come back. “Hef’s wife Crystal went to do a DJ set miles away so she had to stay overnight. But she was still back by 2pm the next day.”
6. No personal carsOn top of the curfew and not being allowed to have jobs, Hefner’s girlfriends weren’t allowed to have personal cars. Whatever they decided to drive would be paid for on loan by Hefner for as long as they were a girlfriend. So their flashy cars could be taken away at a moment’s notice…
7. The mansion was dirtyThe Playboy mansion might have been depicted as a glamorous abode, but in reality it was dated and dirty. Many of Hefner’s girlfriends complained that the many dogs on the property would frequently relieve themselves on the carpets.
“Although we all did our best to decorate our rooms,” Izabella St. James said, “and make them homey, the mattresses on our beds were disgusting — old, worn and stained. “The sheets were past their best too.”
8. The girls had to look a certain wayAlthough this might sound obvious, Hefner’s girlfriends had a strict look that they had to adhere to, and the Playboy founder never held back if they wore something he didn’t approve of or got a haircut he didn’t like. Holly Madison revealed that he told her she looked “old, hard and cheap” when she decided to wear red lipstick. “Hugh wanted white, white hair, with no pigment,” Madison said. Following Hefner’s death, Madison decided not to express her condolences. The other two women who were girlfriends at the same time as her, Bridget Marquardt and Kendra Wilkinson, both took to social media to express there sadness at Hefner’s passing. Despite all starring in The Girls Next Door together, which depicted the three women’s lives with Hefner, only Madison and Marquardt remain friends to this day. Wilkinson openly dislikes Madison and blasted her memoir in 2015, calling it a “re-writing of history.”
9. It felt like prisonAfter a while in Hefner’s strict world, Holly Madison said that it began to feel like a prison. No woman in her early to mid twenties wants to have a curfew, and that is something that Hefner’s widow, Crystal Harris, agreed with when she was interviewed by Howard Stern after leaving Hefner before their planned 2011 wedding. This was worsened by the stigma attached to those who chose to date the Playboy mogul.
“Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in. “Maybe it was the pot and the alcohol, but drowning myself seemed like the logical way to escape the ridiculous life I was leading.”
10. They couldn’t be drunk in picturesIn addition to remaining silent at press events, Hefner’s girlfriends could never appear to be drunk in pictures because this would reflect badly on the Playboy founder. However, it’s common knowledge that many of his girlfriends drank heavily and some even took drugs.
11. Group sex sessionsNeedless to say, with more than one girlfriend sex with Hefner was not a one on one activity. Hefner’s girlfriends would all be in the same room during sex, and they would pretend to get it on with each other as they took turns having sex with him.
12. Hefner encouraged the girls to fightMadison revealed that Hefner loved pitting his girlfriends against each other because it made him feel wanted. This was especially the case when he had seven girlfriends. Izabella St. James, however, said that Holly was the one who loved causing fights between Hefner’s girlfriends, and if a girl joined his hareem that she felt threatened by, she would lie about them to get them kicked out of the mansion. We will never know if Hefner’s former girlfriends’ claims about life with the Playboy mogul are true or not. Whilst the majority of his exes remain positive about their experiences with him, there are some who clearly regret their decision to bed a man old enough to be their grandfather.