11 former Playboy Playmates and ex-girlfriends reveal what life with Hugh Hefner was really like

Britt HayesWed, November 4, 2026 at 11:30 AM UTC

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Holly Madison at Hollywood Life Magazine’s 5th Annual Hollywood Style Awards in West Hollywood; Hugh Hefner at an AIDS Project party at the Playboy mansion on Sept. 17, 1994 in Los Angeles; Crystal Harris at Pure Nightclub in Caesars Palace on July 8, 2011 in Las VegasCredit: Paul Mounce/Corbis/Getty; Ron Davis/Getty; Denise Truscello/WireImage)

From 1953, when Playboy magazine debuted, to his death in 2017 at the age of 91, founder Hugh Hefner cultivated a seemingly enviable lifestyle as America’s quintessential bachelor.

At the epicenter of that lifestyle was the Playboy Mansion. Purchased by Hefner in 1971, it quickly became the site of notorious parties, a popular hangout for celebrities including Jack Nicholson and Arnold Schwarzenegger, and home to a steady stream of women who posed for the magazine — many of whom became Hefner’s girlfriends for a period of time. Despite Hefner’s affinity for the bachelor lifestyle, a couple of those girlfriends even became his wives.

From afar, life at the Playboy Mansion seemed like it was filled with glamour and debauchery, epitomized by Hefner’s daily uniform of silk pajamas and slippers. In 2005, E! premiered The Girls Next Door, a reality show that offered to take viewers inside the wild and crazy life of Hefner and his girlfriends: Holly Madison, Bridget Marquardt, and Kendra Wilkinson. Co-created by Hefner, the series perpetuated the fantasy of the Playboy Mansion and avoided anything that might depict the brand in a negative light, instead focusing on elaborate themed parties, photo shoots, and Hefner’s weekly movie nights.

Following his death in 2017, several women came forward with allegations of sexual misconduct, including former Playmate Susie Krabacher, who accused Hefner of rape in the 2022 docuseries Secrets of Playboy. Prior to the first episode, Playboy’s parent group published an open letter acknowledging the “allegations of abhorrent actions by Playboy founder Hugh Hefner and others,” adding, “We trust and validate women and their stories, and we strongly support the individuals who have come forward to share their experiences.”

So, what was life with Hef at the mansion really like? Here’s what 11 of his ex-girlfriends and former Playboy Playmates have had to say about the experience — both good and bad.

01 of 11

Sondra Theodore

Sondra Theodore during Hugh Hefner Hosts a Tennis and Crumpet Tournament on May 21, 1977 at Playboy Mansion in Beverly HillsCredit: Ron Galella/Getty

In Secrets of Playboy, former Playmate Sondra Theodore says the beginning of her five-year relationship with Hefner was “like a fairytale,” adding, “We were so in love.” Theodore, who dated Hefner until 1981, now describes Hefner as “a monster.”

She says that Hefner decided at the start of their relationship to live a lifestyle more in keeping with the Playboy brand, which included sex with multiple partners. “The group sex was at least five nights a week,” Theodore alleges. “They had a protocol. He liked to direct and you didn’t segue away from it because you could tell it irritated him.” Theodore adds that Hefner “scared me at the end... you couldn’t satisfy him. He wanted more and more and more.”

“I lived a luxury life, yeah, but I paid dearly for it,” she says. “I will never know how to be a normal person.”

02 of 11

Shannon Tweed

Shannon Tweed takes a look at her photo spread in an issue of Playboy in October 1981Credit: Boris Spremo/Toronto Star/Getty

Prior to becoming a well-known B-movie actress, Shannon Tweed posed for Playboy in the early ’80s. In her memoir, Kiss and Tell, Tweed recalled attending Hefner’s infamous annual Midsummer Night’s Dream party in 1981. According to her, the party was attended by “500 nearly naked people,” among them numerous celebrities including Julie Andrews, Magic Johnson, and John Belushi.

That night was the first time Tweed met Hefner, whom she described as “the whole package — handsome, brilliant, charming and, most important, very attentive.” She stayed at the mansion for the next few days, which she described as “the most amazing three days of my life.”

“I saw a little more of what life in the Playboy mansion was like,” Tweed wrote. “There were regular movie screenings, poker and backgammon nights — all kinds of different events where Hef’s friends came over to his house and socialized. The mansion was beautiful, the service was impeccable, and the celebrities were everywhere.”

Tweed said that Hefner asked her to be his girlfriend and move into the mansion after he broke things off with Theodore. She wrote of her relationship with Hefner as “sexual attention and excitement and good times,” adding, “I now had what was practically my very own father figure as a devoted love interest.”

“Hef and I shared a bedroom just like any regular couple, lounging in bed eating Delmonico steak or melon balls off trays. (He loved melon, but only in balls),” Tweed wrote. “We resided in his huge master suite, which had two stories and its own private video library” that included “a wide selection of homemade porno movies” as well as “all his scrapbooks and archives.”

03 of 11

Kimberly Conrad

Hugh Hefner with Kimberly Conrad in the 1980sCredit: Ralph Dominguez/MediaPunch/Getty

Kimberly Conrad became Hefner’s second wife when they married in 1989. The former Playmate of the Year separated from Hefner in 1998, but they stayed married until 2010. Following Crystal Harris’ allegations about her own marriage to Hefner, Conrad took to Instagram to share her perspective.

“I was married to Hef for over 21 years,” Conrad wrote. “We shared a lifetime of beautiful memories, raised 2 wonderful sons together, and had a deeply loving bond that remained strong until his passing on September 27th, 2017 and continues with me to this day.”

“I often told [Hef] if you look up the word gentleman in the dictionary you would find his name and photograph,” she continued. “Hef was in every sense of the word, a true gentleman, kind, loving, generous, philanthropic, and a man of extraordinary character.”

“Losing Hef was devastating, and his absence is still deeply felt,” Conrad concluded. “I had the privilege of knowing and loving the man behind the public image, and I will always treasure the life and memories we shared. I will always believe the world was a better place because he was in it. I am forever grateful and blessed.”

04 of 11

Jenny McCarthy

Jenny McCarthy poses during her “Big Deal” charity fundraiser to benefit “Early Childhood Partial Hospitalization Program at UCLA” at the Playboy Club at the Palms Hotel and Casino Resort on Aug. 4, 2007 in Las VegasCredit: Denise Truscello/WireImage

Posing for Playboy in 1993 launched Jenny McCarthy’s career as a model and eventual TV personality. While she never dated Hefner, she spent time at the mansion, which she said was “run like a strict dormitory.”

“Like, we weren’t even allowed near Hef or around the house. It was almost like Catholic school, to be honest. There were no orgies or big parties going on,” she explained on a 2022 episode of the #NoFilter With Zack Peter podcast. “So, I think I went in there in a window of time that was kind of safe.” McCarthy said that she didn’t participate in the Secrets of Playboy docuseries because the subject matter didn’t reflect her experience at the mansion, but, “hearing their stories, my heart broke for a lot of these women.”

During a 2024 appearance on Watch What Happens Live, she reiterated that her experiences with Hefner and the mansion were different from some of her peers. “I was there when his kids were throwing bacon at me in high chairs. It was the perfect time,” said McCarthy, whose time in Hefner’s orbit coincided with his marriage to Conrad. Even though Hefner was playing the role of family man during this period, McCarthy recalled, “There was so much, still, sex going on with gross celebrities in the grotto areas and stuff like that.”

“Unfortunately, for every 20 guys, it was 1 girl. So the guys were just in heaven. But also the guys were over 70 years old,” she continued. “Oh God, they were like, really, really old. It was like Viagra central.”

05 of 11

Izabella St. James

Izabella St. James at the Linea Pelle 20th Anniversary Party at Pacific Design Center in West Hollywood in October 2010Credit: John Shearer/WireImage

As she recounted in her book, Bunny Tales: Behind Closed Doors at the Playboy Mansion, Izabella St. James moved into the mansion in 2002 and stayed until 2004. Along with Madison, St. James was one of Hefner’s “official” girlfriends during this time, and her memories of life at the mansion aren’t always pleasant.

“Hef was used to dirty carpets,” St. James wrote. “The one in his bedroom had not been changed for years, and things became significantly worse when Holly Madison moved into his room with him as Girlfriend No. 1 soon after I moved in, bringing her two dogs. They weren’t house-trained and would just do their business on the bedroom carpet. Late at night or in the early hours of the morning — if any of us visited Hef’s bedroom — we’d almost always end up standing in dog mess. Everything in the Mansion felt old and stale, and Archie the house dog would regularly relieve himself on the hallway curtains, adding a powerful whiff of urine to the general scent of decay.”

Like several of her peers, St. James didn’t enjoy the process of getting her weekly allowance from Hefner. “Every Friday morning 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: a thousand dollars counted out in crisp hundred-dollar bills from a safe in one of his bookcases,” she wrote. “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.”

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06 of 11

Holly Madison

Holly Madison attends Byblos Event at the Playboy Mansion on Feb. 21, 2008 in Beverly HillsCredit: Patrick McMullan/Getty

On their podcast Girls Next Level, former Girls Next Door stars Madison and Marquardt have openly discussed the ups and downs of their lives at the mansion. In an August 2022 episode, Madison, who was in a relationship with Hefner from 2001 to 2008, described the requirement to have sex with the Playboy founder as a “chore.”

“Everybody wanted to get this over with as quickly as possible. None of the females were into it, like sorry to burst the bubble,” Madison said. “We thought of it as a chore that we had to do or else we’ll get kicked out of the house and everybody just wanted to make it go by as quickly as possible.”

“I can’t explain to you guys how embarrassing that whole routine was, especially as we got later down the road when there would be, like, a lot of conflict with the other girls,” she continued. “You’re literally sitting there naked having sex in front of a group of people who hate you and talk s--- about you while you’re having sex and you can hear it. It was just, like, hell.”

During a September 2022 episode of Girls Next Level, Madison and Marquardt recalled one of Hefner’s particularly “disgusting” habits: using baby oil as lubricant. After explaining that it caused “irritation” and that her gynecologist advised her to stop using it, Madison said, “It got to the point where I refused to use it, but then other people would tell me that he would — in the bedroom — put it on his hand and then put it on me when my back was turned and I didn’t know he was doing it.”

Madison has also said that one of the strangest parts of living in the Playboy Mansion was the constant availability of products intended for sex in every room. “They would have these trays everywhere, like in every bathroom, out on the tennis courts, by the pool, and it would be a tray with Kleenex, Pepto Bismol, Vaseline, baby oil, sunscreen — any kind of makeshift lube,” she told PEOPLE. “It was weird.”

07 of 11

Bridget Marquardt

Bridget Marquardt attends the Playboy Launch of a new men’s fragrance at The Hotel on Rivington on Oct. 30, 2008 in New York CityCredit: Michael Loccisano/FilmMagic

On the August 2022 episode of Girls Next Level, Marquardt, who was in a relationship with Hefner from 2002 to 2009, described the first time she had sex with him as “disappointing and embarrassing.” She was also put off by the state of Hefner’s bedroom, which sounds nothing like the sort of place where anything resembling “magic” happens. “I was shocked at how messy it was,” Marquardt said. “We walked in and it was just a disaster in there. The lights were out, but there were two giant TV screens in there that were playing porn… There’s just so much junk.”

In a subsequent episode, Marquardt described the little black book that Hefner used to track various aspects of their lives, including their weekly allowances. “The black book kept track of a few different things. It kept track of when somebody collected their allowance — he would mark it off so you couldn’t ask for it twice,” she explained. “But it also kept track of who slept with him and when.” She added that “It was just very uncomfortable asking for allowance... A lot of times, I wouldn’t ask for it for weeks at a time.”

08 of 11

Kendra Wilkinson

Kendra Wilkinson arrives at the Celebrity Lock Room presents “An All Star Night at the Mansion” at the Playboy Mansion on July 11, 2006 in Los AngelesCredit: Michael Buckner/Getty

Wilkinson has a decidedly different take on her relationship with Hefner, which lasted from 2004 to 2008. “It was like heaven, it was a heavenly experience for me,” she said on a May 2025 episode of the Skinny Confidential podcast. “Like there couldn’t have been a better experience.”

“I have bad experiences when it comes to the business side of things,” Wilkinson continued. “Not Hef. Hef was a very awesome guy to me. He was a generous, nice person. A very nice person. I don’t see him in any other way.”

Wilkinson has been critical of her time at the mansion in the past, however. In 2009, she told Us Weekly that she would “sneak” around to have sex with other people, and that outside of filming Girls Next Door, she actually didn’t see Hefner that often. “Besides the nights we went out, I only saw Hef, like, once a day walking through the halls to his office. There were never solo dates,” she said. “The most we kind of say to each other is, ‘I love you,’ ‘Love you too,’ ‘I hope you have a good day,’ ‘Did you have a good day?’”

Wilkinson said that when Hefner would go over his little black book every morning, it made her “insane,” and that she resented the weekly $1,000 allowance. “I hate putting my hand out, but we couldn’t have jobs other than getting appearance fees,” she said.

09 of 11

Crystal Harris

Crystal Harris attends Wet Republic on June 18, 2011 in Las VegasCredit: Denise Truscello/WireImage

Crystal Harris was 26 years old when she married an 86-year-old Hefner in 2012. They remained married until his death, after which Harris spoke affectionately of Hefner. But in 2024, Harris published the memoir Only Say Good Things: Surviving Playboy and Finding Myself, in which she reexamines her relationship with the Playboy founder, who allegedly made her promise to “only say good things” when he died.

“A lot of women that have been in Hef’s orbit, they’ve lost their sparkle,” Harris told PEOPLE following the publication of her book. Commenting on Hefner’s affinity for younger women, Harris said that girls as young as 11 would send the Playboy founder letters in which they asked to live at the mansion after watching episodes of The Girls Next Door. “He would tell them to wait until they were 18,” Harris alleged. “It’s horrifying how The Girls Next Door glorified it. It’s sad and it’s awful.”

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Like her predecessors, Harris wrote in her book that she also had a curfew, though hers was much earlier than the previous standard of 9 p.m. “The pantry staff would start frantically calling my phone at exactly 6:01 p.m.,” she recalled. “And then I would run in, pushing through the heavy wooden door, and go find Hef, so I could kiss him on the cheek and show him: Here I am, I’m home, I’ve followed the rules.”

As for the mansion itself, “It was like a time capsule from the ’70s. Like Hef had pushed pause at the height of his heyday and never unfrozen it,” Harris wrote. Though it was ostensibly a lovely home, Harris told PEOPLE, “over time, I saw that this place doesn’t really get cleaned that well and there’s mold. It just felt rundown and gross after a while.”

More recently, in October 2026, Harris publicly asked Jessica Biel to reconsider portraying Hefner’s wife in an upcoming film about life in the mansion.

10 of 11

Kristina and Karissa Shannon

Karissa Shannon and Kristina Shannon attend the Spring 2009 Mercedes-Benz Fashion Week held at Smashbox Studios on Oct. 13, 2008 in Culver City, CalifCredit: Katy Winn/Getty

Twins Kristina and Karissa Shannon were 18 or 19 years old when they moved into the Playboy mansion in 2008. Alongside Harris, they joined the final season of The Girls Next Door as Hefner’s new girlfriends. Upon arriving at the mansion, they quickly discovered that “what they show on TV and on the show was a 100 percent different from what was going on behind the scenes,” Kristina later told PEOPLE.

The sisters described tension between themselves and the other women in the house, which they attributed to their younger age. As they alleged to Us Weekly in 2025, they also felt a lack of agency while living in the mansion. “[Hefner] put us on ‘room arrest’ when we tried to leave several times. Room arrest is when he has security sit outside your bedroom door, and they don’t let you leave,” the sisters said jointly. “We were teenagers. He took full advantage.”

11 of 11

Carla and Melissa Howe

Playboy Radio personalities Carla Howe and Melissa Howe at the 8th annual BTE All-Star Celebrity Kickoff Party at The Playboy Mansion on July 15, 2013 in Beverly HillsCredit: Paul Archuleta/FilmMagic

British twin sisters Carla and Melissa Howe were 18 when they first posed for Playboy. They stayed at the mansion “on and off” for four years beginning in 2011, when they first met Hefner. “We were already working for the Playboy brand and we got told Hef wanted to meet us. He was the perfect gentleman — not pervy at all,” Melissa told U.K. publication The Mirror. “It was so fun being there. It was such a huge, amazing house.”

Like several of their peers, the sisters said they had to adhere to Hefner’s rules, including a strict 9 p.m. curfew. “You’re definitely not allowed male visitors. If you break the rules you get banned,” Carla told The Mirror in a separate interview. “Once you’re out, you’re out, you can’t come back.”

The Howe sisters said they never had a sexual relationship with Hefner, which they attributed to his age and relationship with Harris. Although they described a more physically frail version of Hefner, the sisters added that he was still sharp when it came to business. “He reads everything about the mansion,” said Carla. “He gets press clippings brought every day with a box of his favourite doughnuts. He still sees it as a business, so you’d be surprised how strict it is.”

“If you do something wrong, you’ll get an email. There’s a strict code of conduct. There are even rules about Instagram and Twitter,” Melissa added. “You’ve got to show everything in a good light and if you’re drunk in a picture you’ll be in trouble.”

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