10 Strict Rules Hugh Hefner Allegedly Forced His Girlfriends To Follow

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Hugh Hefner girlfriends

Hugh Hefner was the founder and editor-in-chief of the entertainment magazine and brand Playboy. 

The first issue featured Marilyn Monroe in 1953 and continued to grow into a multi-billion dollar business, despite the fact that when the late Hugh Hefner used "the famous Marilyn Monroe nude" to launch the men's magazine, Monroe hadn't consented to the then-four-year-old images' use, nor had Hefner directly paid her a dime.

Hefner lived in the Playboy Mansion in Hollywood which was known to hold extravagant and wild parties. He passed away in 2017 at the age of 91 and was laid to rest at Westwood Memorial Park in Los Angeles, in the crypt beside Marilyn Monroe, for which he paid $75,000.

The founder was known to always keep a group of younger women around him as his playmates and girlfriends. This even inspired the series “The Girls Next Door” which seemed to showcase life inside the mansion. 

However it was not all it seemed.

Here are the the strict rules Hugh Hefner allegedly forced his girlfriends to follow. 

1. No red lipstick was allowed.

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Hugh Hefner with a group of women

One of Hefner’s girlfriends, Marquadt admitted in the documentary “Secrets of a Playboy” Hefner forbade other playboy bunny Holly Madison from wearing red lipstick. 

According to Buzzfeed News, “(Madison) 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.” 

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2. There was a 9 p.m. curfew

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Holly Madison and Kendra Wilkinson kissing Hugh on the cheek

Playboy model, Jenna Bentley revealed to Dailymail, “what you got in return was unbelievable. I mean, even though we had a 9pm curfew it wasn’t like we were prisoners” Bentley said. 

“Although if you missed curfew you were sleeping on the lawn. They were very strict about it,” she said. 

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3. Girls got a weekly clothing allowance.

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Hefner and playmates on red carpet

The Playboy founder would give $1,000 allowances to the girls on Friday’s in $100 bills according to Grunge. 

However this was also time for the girls to get feedback. 

"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," according to Izabella St. James.

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4. The girls had to be quiet when Hefner was speaking.

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Hugh Hefner and girlfriends

According to Do You Remember, the girls must be quiet when Hefner is giving interviews, “probably because a man is speaking and Hef is still living in 1963.”

Several “bunnies” have seemed to have spoken out about how difficult it was to live in the mansion. 

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5. The women were not allowed to date other guys.

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Hugh Hefner with Holly

According to the Lad Bible, Holly Madison admitted the curfew didn’t allow for much time dating — which was also another rule. 

She said, "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.

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6. The girls were not allowed to have an apartment.

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Bridget, Holly, and Kendra at Halloween party

Holly Madison, who has compared living in the Playboy Mansion to a cult, said the girls were not allowed to have their own apartment while living there. 

"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" she said to Lad Bible. 

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7. The girls had to have blonde hair.

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Hugh Hefner and Holly Madison

Madison, who soon became Hefner’s number one girlfriend, has since revealed several of the restrictions there were for being one of his ‘girlfriends.’ One of them was that Hefner specifically wanted “busty blondes with bright-blonde hair” according to Do You Remember?

"You were expected to look a certain way obviously, you had to have the blonde hair," Madison said to Lad Bible. 

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8. Kendra Wilkinson said her job included one minute sex with Hefner.

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Kendra Wilkinson

According to The Sun, Wilkinson was asked to move into the Playboy Mansion after she was hired to be a naked statue at his 78th birthday party. 

“I moved in and weeks went by and I didn’t know that sex was involved,” Wilkinson said.  

However, she would go on to have one minute sexual encounters with him that felt like a job. 

“I was usually very drunk during those evenings. I tended not to care about much until the next day. I had to be very drunk or smoke lots of weed to survive those nights,” she said to The Sun. 

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9. Hefner held twice-weekly orgies for him and his girlfriend.

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Hugh Hefner with woman at Grammys

In Holly Madison’s 2015 autobiography “Down The Rabbit Hole” she revealed Hefner held twice-weekly orgies where he would give out sedative drugs, according to The Sun. 

Madison ended up leaving the mansion in 2006 when she found out Hugh was infertile, The Sun reported. 

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10. They had to sign NDAs upon entering the house.

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Hugh Hefner with wife

Playboy model, Jenna Bentley said to Dailymail that she had to sign an ‘iron-clad’ non-disclosure agreement, meaning she can not reveal all she’s seen. 

She has insisted that she never slept with him but walked in on him having sex one time. 

“I obviously can never say who it was with, all I can say is that there were four people including him” she said. 

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Sydney Taylor is a writer who focuses on News and Entertainment topics.