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

Ahead of the ‘Secrets of Playboy’ docuseries – that promises to declare the ‘hidden truths’ about Hugh Hefner – discover about the females who dated Hef.

Hugh Hefner had many partners earlier than his death in 2017 at the age of 91…and diverse them will declare their yarn in Secrets of Playboy. The ten-episode A&E docuseries will ruin down boundaries and inform the reality” while offering an “unflinching seek for at the non-public outcomes of Hugh Hefner’s empire, while moreover exploring his legacy’s higher have an effect on on our society and standard-day views of sexuality,” per Time restrict.

At some stage in Hugh Hefner’s life, the Playboy creator was as soon as married three cases: first to Mildred Williams, from 1944 to 1946; to Kimberley Conrad from 1989 to 2010, despite the undeniable reality that the couple separated in 1998; and to Crystal Harris from 2012 to his death in 2017. However, in between those gaps, Hugh was as soon as rarely single. The person continuously had a girl – and in a variety of cases, two or three – on his arm. Listed below are honest some females who contain arrive so far Hugh Hefner.

Barbara Lynn Klein / Barbi Benton

(Bob Dear/AP/Shutterstock)

Barbara Lynn Klien — higher identified to the arena as Barbi Benton, singer, and well-known person of Hee-Haw and Deathstalker — first met Hugh in 1968 on the distance of his television show camouflage, Playboy After Murky, in line with PEOPLE. She was as soon as 18, and he was as soon as 42, and the age gap was as soon as one motive she wasn’t drawn to him originally. However, Hugh set aside the enchantment on her – and he set aside her on the conceal of Playboy four cases – in 1969, 1970, 1972, and 1985 (h/t Insider).

He was as soon as very romantic,” she informed Of us. “He was as soon as one in all the most romantic males I’ve ever met. He was as soon as continuously rubbing my neck, preserving my hand, squeezing me, and making me if truth be told feel loved. He was as soon as moreover affectionate with other ladies … and he loved kissing. I didn’t mind, because I was as soon as very stable in our relationship.”

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

Sondra Theodore


Sondra Theodore was as soon as romantically concerned with Hugh Hefner from 1976 to 1981. She was as soon as 19 after they first met. He was as soon as 50. Sondra was as soon as the July 1977 Playmate of the Month and lived within the Playboy Mansion. Ahead of the Secrets of Playboy docuseries, Sondra informed Leisure Tonight that she was as soon as “groomed” by Hefner. “I noticed a person alive to about intercourse, couldn’t bag passable of it and [it] wasn’t ever passable for him. He bought bored with out problems and the taboo was as soon as something he searched out.”

Shannon Tweed

(Eric Charbonneau/Shutterstock)

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

“While you glance footage of him in proper garments, those contain been the ones I purchased him,” she informed CKOM in 2017, noting that she bought Hugh to costume in something as antagonistic to his trademark pajamas. “He appeared very trim in his garments.”

Shannon renowned that Hugh was as soon as supportive of females’s rights. “What he wished to claim was as soon as,” she mentioned,” it’s okay for females to favor to contain intercourse and to no longer if truth be told feel embarrassed or slut shamed about it. And it’s okay for females to favor the identical things males favor.” In 1983, she met Gene at a Playboy mansion party, fell in like, and has been with him ever since.

Carrie Leigh

(Alison Vibrant/AP/Shutterstock)

Carrie “lived with Hefner for 5 years within the 1980s,” in line with a 1999 article within the Washington Publish. She was as soon as listed as being 22 in a 1986 Rolling Stone article (Hugh, at the time, was as soon as turning 60.) “I’ve been a model since I was as soon as 14,” she informed RS. “I came here to achieve duvet assessments. I had by no approach if truth be told regarded as being a Playmate. It wasn’t like I was as soon as from a town in Ohio and didn’t know what was as soon as going on.”

A Canadian from Vancouver, Carrie was as soon as 20 when she stayed at the Playboy mansion while attempting out for a describe session. “I bear in mind the evening quite smartly,” Hef informed RS. “I was as soon as playing Monopoly. It was as soon as one in all those things where you seek for all around the room and. . .something occurs. Proper two weeks earlier, my relationship with [Playmate] Shannon [Tweed] had ended. And I was as soon as resolute no longer to alter into concerned all over again. Nonetheless the mutual enchantment was as soon as very glaring. We fell for one one more.”

After they broke up, Carried filed – then dropped – a $35 palimony swimsuit, then sued him for publishing unauthorized photos of her. She informed the Washington Publish that she left Hef for the reason that Playboy life was as soon as constricting. “It’s nearly like a cult,” she mentioned in 1999. “While you live in an environment like that that’s so diverse from how folk live, you launch forgetting who you is prone to be and what you imagine is honest. It’s just like the music ‘Hotel California’–‘Mirrors on the ceiling, pink champagne on ice. We’re all honest prisoners here.’ ? ‘It’s most likely you’ll perchance are attempting any time you love, however that you just can by no approach leave’? It took me a couple of years after I did leave to wipe it out of my head.”

Brande Roderick


After Hugh and Kimberley Conrad separated in 1998, he saved himself busy by dating a handful of Playmates, in conjunction with Brande Roderick. Ahead of the Secrets of Playboy docuseries, she spoke with NewsNation’s Asheligh Banfield and defended her stale flame. “Hef was as soon as a just appropriate-looking person,” she mentioned. “I if truth be told feel so sad that I contain to protect him because he’s (was as soon as) such an wonderful person that has achieved so worthy for thus many folks,” she mentioned, per Page Six. “And the undeniable reality that some females are popping out because they’ve a book popping out (or) they wish 15 more minutes of repute.. and to achieve it now may perchance be disgusting.”

Hugh informed The Each day Beast in 2017 that he was as soon as “roughly beat up emotionally and bruised,” after his marriage to Conrad. “And I started dating an actress named Brande Roderick, and nearly at the identical time met a pair of twins named Sandy and Mandy Bentley. For the following two years, my live-in girlfriends contain been Brande, Mandy, and Sandy—which reads like obnoxious fiction, however was as soon as honest.”

“When the relationship with Brande broke up, I added more ladies. At one point, it was as soon as as much as seven. Izabella was as soon as one in all those seven.”

Tina Marie Jordan

Tina Marie Jordan, who was as soon as Playmate of the Month for March 2002, was as soon as instant concerned with Hugh from 2000 to 2001. She co-hosted the Two Chicks and a Bunny radio show camouflage 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: At the wait on of Closed Doorways at the Playboy Mansion. The memoir claims that Hugh was as soon as any individual who saved his blonde girlfriend posse on a tight lease, devoured Viagra handiest to “lay there like a tiring fish.”

Hugh confirmed one of the crucial allegations – that his girlfriends bought a $1,000 per week allowance and had to stick to a 9 p.m. curfew – while denying some while talking to The Each day Beast. “Despite what she writes, [Izabella] didn’t leave of her be pleased volition. She left because she was as soon as requested to switch away because she didn’t bag alongside with one of the crucial replacement ladies. She was as soon as in battle with one of the crucial nicer ladies like Holly [Madison] and Bridget [Marquardt], and I roughly cleaned house.”

“Certainly one of many things that space my relationships other than many others is the undeniable reality that I contain managed to remain end to many of my stale girlfriends, in conjunction with my stale other halves, because I’m human being,” claimed Hefner. “And I contend with females very smartly. I purchase pride in that.”

Holly Madison / Bridget Marquardt / Kendra Wilkinson

Matt Sayles/AP/Shutterstock

Per chance the most high-profile instance of Hugh’s polyamory was as soon as E! ‘s actuality television series, The Ladies Next Door, which featured Hugh and his three girlfriends – Holly Madison, Bridget Marquardt, and Kendra Wilkinson.

Holly shared her tales of Hugh with the Secrets of Playboy docuseries. “There was as soon as with out a doubt no, like, romance or seduction or anything else like that,” she mentioned. “It was as soon as darkish within the room, however there was as soon as a huge movie camouflage of porn in front of the mattress. He [Hefner] was as soon as within the center of the mattress, after which the females contain been surrounding him, however they’re all backlit.”

“It was as soon as all very mechanical and robotic, and also you may perchance roughly educate the replacement females’s lead, and it was as soon as if truth be told wrong to me how Hef didn’t favor to utilize protection,” she added. “The affect it had on me was as soon as so heavy.”

Holly has clashed with Kendra within the past, particularly over their experiences with Hefner.

Karissa & Kristina Shannon

(Jim Ruymen/UPI/Shutterstock)

After Holly, Kendra, and Bridget, Hugh moved on to twins Kristina and Karissa Shannon. The romance was as soon as transient. The two moved out of the Playboy Mansion and into the nearby Playboy Home in 2010 when Hugh bought concerned with Crystal Harris. When the twins brought house some young boyfriends, Hefner reportedly requested the twins to switch out.

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