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Hugh Hefner’s wife Crystal revealed extremely strict list of rules he had for his girlfriends

Home> Entertainment> Celebrity

Published 14:33 15 Oct 2025 GMT+1

Hugh Hefner’s wife Crystal revealed extremely strict list of rules he had for his girlfriends

Hugh Hefner's third and last wife Crystal has opened up on what would really go on behind closed doors in the Playboy Mansion

Madison Burgess

Madison Burgess

Featured Image Credit: Denise Truscello/WireImage

Topics: Celebrity, Dating, Hugh Hefner, Life, Real Life, True Life, Entertainment

Madison Burgess
Madison Burgess

Madison is a Journalist at Tyla with a keen interest in lifestyle, entertainment and culture. She graduated from the University of Sheffield with a first-class degree in Journalism Studies, and has previously written for DMG Media as a Showbiz Reporter and Audience Writer.

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Hugh Hefner's widow, Crystal, has revealed the long list of rules he had set in place for his girlfriends - and they were all to do with appearance.

Playboy Magazine founder Hefner moved into his Los Angeles home, more commonly known as the Playboy Mansion, in the early 1970s, and he lived there until he died of sepsis brought on by an E. coli infection in 2017.

The father-of-four famously had a plethora of live-in girlfriends who resided alongside him, including Holly Madison, Kendra Wilkinson, and Crystal, who became his third wife and eventual widow.

Crystal Hefner, now 39, was just 21 years old when she first met Hugh - who was 60 years her senior at the time - in 2008.

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Following the media mogul's death, many of his former girlfriends, ex-wives, and employees have come forward with stories about what it was really like in the famous Playboy Mansion.

And as to be expected, not a whole lot of it is positive.

It's been revealed that Hugh Hefner had strict rules in place for his girlfriends (SGranitz/WireImage)
It's been revealed that Hugh Hefner had strict rules in place for his girlfriends (SGranitz/WireImage)

Crystal has since claimed that Hefner would control almost everything about the girls - from their hair colour to having their nails done, there were some strict rules to follow.

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According to People, she said: "Our nail polish couldn’t be anything but some neutral colour, no French manicure."

She claims he would also critically point out her dark roots every time they would start to grow through the blonde.

Crystal recalled: "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."

Other rules were: 'Don’t have a belly button ring because that’s trashy' and you have to 'wear the flag' (aka Playboy logo shirts) which Crystal said were 'uncomfortable and cheap'.

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Further opening up on what the state of the house itself was like, she revealed it was actually quite 'run down and gross' despite Hefner wanting all the women to look a certain way.

She told the publication: "This place doesn’t really get cleaned that well and there’s mould, and it just felt just kind of run down and gross after a while.

"Too, too many parties. It was worn out.”

She added that sadly the animals on the property began to die.

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Hefner's widow Crystal admitted that he would control almost everything about the girls (Jerod Harris/Getty Images)
Hefner's widow Crystal admitted that he would control almost everything about the girls (Jerod Harris/Getty Images)

For those who don't know, Hefner reportedly had a zoo license meaning he could keep exoctic animals on his property, including monkeys, peacocks, and toucans.

“I feel like I was constantly crying for everything and everybody there. All those animals were so depressed and sad-looking. It was all an illusion. I don’t even know if I was happy, to be honest," Crystal said.

Meanwhile, some of Hugh's other former girlfriends have also opened up more of the strict rules.

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According to Izabella St. James, one of Hugh's former girlfriends, he called for all housemates to be back at the mansion by no later than the watershed.

She told Fox News Digital, "We had to be home by 9pm. 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."

Fraternising with the staff was also firmly not allowed unless absolutely necessary.

Holly Madison, Hefner's 'main' girlfriend, wrote in her memoir: "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."

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