Hugh Hefner Girlfriends Through The Years, Including Holly Madison, Bridget Marquardt, & Kendra Wilkinson

Ahead of the 'Secrets of Playboy' docuseries – that promises to tell the 'hidden truths' about Hugh Hefner – learn about the women who dated Hef.

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Hugh Hefner had many partners before his death in 2017 at the age of 91…and many of them will tell their story in Secrets of Playboy. The ten-episode A&E docuseries will break down barriers and expose the truth” while offering an “unflinching look at the personal effects of Hugh Hefner’s empire, while also exploring his legacy’s larger influence on our society and modern-day views of sexuality,” per Deadline.

During Hugh Hefner’s life, the Playboy creator was married three times: first to Mildred Williams, from 1944 to 1946; to Kimberley Conrad from 1989 to 2010, though the couple separated in 1998; and to Crystal Harris from 2012 to his death in 2017. However, in between those gaps, Hugh was rarely single. The man always had a woman – and in many cases, two or three – on his arm. Here are just some women who have come to date Hugh Hefner.

Barbara Lynn Klein / Barbi Benton

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Barbara Lynn Klien — better known to the world as Barbi Benton, singer, and star of Hee-Haw and Deathstalker — first met Hugh in 1968 on the set of his television show, Playboy After Dark, according to PEOPLE. She was 18, and he was 42, and the age gap was one reason she wasn’t interested in him at first. However, Hugh put the charm on her – and he put her on the cover of Playboy four times – in 1969, 1970, 1972, and 1985 (h/t Insider).

He was very romantic,” she told People. “He was one of the most romantic men I’ve ever met. He was always rubbing my neck, holding my hand, squeezing me, and making me feel loved. He was also affectionate with other girls … and he loved kissing. I didn’t mind, because I was very secure in our relationship.”

Hef convinced her to change her name to Barbi Benton, and she’s credited with convincing Hugh to buy the Playboy Mansion in Holmby Hills. They broke up in 1976, and she married George Gradow in 1979.

Sondra Theodore


Sondra Theodore was romantically involved with Hugh Hefner from 1976 to 1981. She was 19 when they first met. He was 50. Sondra was the July 1977 Playmate of the Month and lived in the Playboy Mansion. Ahead of the Secrets of Playboy docuseries, Sondra told Entertainment Tonight that she was “groomed” by Hefner. “I saw a man obsessed with sex, couldn’t get enough of it and [it] wasn’t ever enough for him. He got bored easily and the taboo was something he searched out.”

Shannon Tweed

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Before Shannon Tweed was Gene Simmons’ better half, the actress and model briefly dated Hugh Hefner. She met Hugh when she was 24 and attended a Playboy mansion party. The two dated for two years, which coincided with her being named 1982’s Playmate of the Year.

“When you see pictures of him in real clothes, those were the ones I got him,” she told CKOM in 2017, noting that she got Hugh to dress in something other than his trademark pajamas. “He looked very smart in his clothes.”

Shannon noted that Hugh was supportive of women’s rights. “What he wanted to say was,” she said,” it’s okay for women to want to have sex and to not feel embarrassed or slut shamed about it. And it’s okay for women to want the same things men want.” In 1983, she met Gene at a Playboy mansion party, fell in love, and has been with him ever since.

Carrie Leigh

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Carrie “lived with Hefner for five years in the 1980s,” according to a 1999 article in the Washington Post. She was listed as being 22 in a 1986 Rolling Stone article (Hugh, at the time, was turning 60.) “I’ve been a model since I was 14,” she told RS. “I came here to do cover tests. I had never really thought of being a Playmate. It wasn’t like I was from a town in Ohio and didn’t know what was happening.”

A Canadian from Vancouver, Carrie was 20 when she stayed at the Playboy mansion while trying out for a photo session. “I remember the evening quite well,” Hef told RS. “I was playing Monopoly. It was one of those things where you look across the room and. . .something happens. Just two weeks earlier, my relationship with [Playmate] Shannon [Tweed] had ended. And I was determined not to get involved again. But the mutual attraction was very obvious. We fell for each other.”

After they broke up, Carried filed – then dropped – a $35 palimony suit, then sued him for publishing unauthorized photos of her. She told the Washington Post that she left Hef because the Playboy life was constricting. “It’s almost like a cult,” she said in 1999. “When you live in an environment like that that’s so different from how other people live, you start forgetting who you are and what you believe is right. It’s like the song ‘Hotel California’–‘Mirrors on the ceiling, pink champagne on ice. We’re all just prisoners here.’ You know? ‘You can check out any time you like, but you can never leave’? It took me a few years after I did leave to wipe it out of my head.”

Brande Roderick


After Hugh and Kimberley Conrad separated in 1998, he kept himself busy by dating a handful of Playmates, including Brande Roderick. Ahead of the Secrets of Playboy docuseries, she spoke with NewsNation’s Asheligh Banfield and defended her former flame. “Hef was a wonderful person,” she said. “I feel so sad that I even have to defend him because he’s (was) such an amazing person who has done so much for so many people,” she said, per Page Six. “And the fact that some women are coming out because they have a book coming out (or) they want 15 more minutes of fame.. and to do it now is disgusting.”

Hugh told The Daily Beast in 2017 that he was “kind of beat up emotionally and bruised,” after his marriage to Conrad. “And I started dating an actress named Brande Roderick, and almost at the same time met a pair of twins named Sandy and Mandy Bentley. For the next two years, my live-in girlfriends were Brande, Mandy, and Sandy—which reads like bad fiction, but was true.”

“When the relationship with Brande broke up, I added more girls. At one point, it was up to seven. Izabella was one of those seven.”

Tina Marie Jordan

Tina Marie Jordan, who was Playmate of the Month for March 2002, was briefly involved with Hugh from 2000 to 2001. She co-hosted the Two Chicks and a Bunny radio show with  Kerri Kasem and Galen Brown on KLSX 97.1

Izabella St. James


Izabella St. James – born Izabella Katarina Kasprzyk – dated Hugh following his breakup with Brande. She moved into the Playboy Mansion in 2002 and moved out two years later. In 2006, she wrote Bunny Tales: Behind Closed Doors at the Playboy Mansion. The memoir claims that Hugh was someone who kept his blonde girlfriend posse on a tight lease, devoured Viagra only to “lay there like a dead fish.”

Hugh confirmed some of the allegations – that his girlfriends got a $1,000 a week allowance and had to adhere to a 9 p.m. curfew – while denying some while talking to The Daily Beast. “Despite what she writes, [Izabella] didn’t leave of her own volition. She left because she was asked to leave because she didn’t get along with some of the other girls. She was in conflict with some of the nicer girls like Holly [Madison] and Bridget [Marquardt], and I kind of cleaned house.”

“One of the things that set my relationships apart from many others is the fact that I have managed to remain close to many of my former girlfriends, including my former wives, because I’m a decent human being,” claimed Hefner. “And I treat women very well. I take pride in that.”

Holly Madison / Bridget Marquardt / Kendra Wilkinson

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Perhaps the most high-profile example of Hugh’s polyamory was E! ‘s reality television series, The Girls Next Door, which featured Hugh and his three girlfriends – Holly Madison, Bridget Marquardt, and Kendra Wilkinson.

Holly shared her stories of Hugh with the Secrets of Playboy docuseries. “There was definitely no, like, romance or seduction or anything like that,” she said. “It was dark in the room, but there was a giant movie screen of porn in front of the bed. He [Hefner] was in the middle of the bed, and then the women were surrounding him, but they’re all backlit.”

“It was all very mechanical and robotic, and you would kind of follow the other women’s lead, and it was really gross to me how Hef didn’t want to use protection,” she added. “The impact it had on me was so heavy.”

Holly has clashed with Kendra in the past, especially over their experiences with Hefner.

Karissa & Kristina Shannon

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After Holly, Kendra, and Bridget, Hugh moved on to twins Kristina and Karissa Shannon. The romance was brief. The two moved out of the Playboy Mansion and into the nearby Playboy House in 2010 when Hugh got involved with Crystal Harris. When the twins brought home some young boyfriends, Hefner reportedly asked the twins to move out.

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