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Former Playboy model Kendra Wilkinson makes sad admission about sex after relationship with Hugh Hefner

Home> Entertainment> Celebrity

Updated 10:39 25 Mar 2025 GMTPublished 18:19 24 Mar 2025 GMT

Former Playboy model Kendra Wilkinson makes sad admission about sex after relationship with Hugh Hefner

The reality TV star resided in the Playboy Mansion for five years

Rhianna Benson

Rhianna Benson

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Featured Image Credit: John Sciulli/WireImage for Ogilvy Public Relation

Topics: Celebrity, Reality TV, US News, Playboy

Rhianna Benson
Rhianna Benson

Rhianna is an Entertainment Journalist at LADbible Group, working across LADbible, UNILAD and Tyla. She has a Masters in News Journalism from the University of Salford and a Masters in Ancient History from the University of Edinburgh. She previously worked as a Celebrity Reporter for OK! and New Magazines, and as a TV Writer for Reach PLC.

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US media personality Kendra Wilkinson has revealed that her relationship with late Playboy boss Hugh Hefner had a devastating impact on her personal life.

Despite being one of the magazine CEO's famous 'bunnies' - with the x-rated modelling gig sky-rocketing her into stardom - she has far from fond memories of her time in the California castle.

The year was 2004, and Wilkinson was just 18 when she first came face-to-face with Hefner, having been invited to his 78th birthday party as a 'painted girl', with the reality TV star immediately catching the millionaire's eye.

The mother-of-two claimed the experience left her with intimacy issues (JC Olivera/Variety via Getty Images)
The mother-of-two claimed the experience left her with intimacy issues (JC Olivera/Variety via Getty Images)

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Within a matter of weeks, she'd moved into the Playboy Mansion along with Hefner's other girlfriends, Holly Madison and Bridget Marquardt, and remained at the property for five years until 2009.

Wilkinson's relationship with the media mogul cemented her position as a much-loved reality star, who later went on to front several television series - including Girls Next Door, and her own shows, Kendra and Kendra On Top.

Only recently, however - following Hefner's death in 2017, aged 91 - has Wilkinson opened up about the realities of being one of his lovers.

Speaking on Friday's instalment (21 March) of the Amy & T.J. podcast, she told listeners: "Look, I struggle still to this day with my relationships and my views on sex."

The 39-year-old then went on to confess that she had to 'go through a lot of therapy'.

"They looked at me and they’re like — this is the first time I’m admitting this — but they’re like, 'You might have a little bit of a sex problem. You have a little bit of a problem when it comes to thinking of sex'," she explained.

Wilkinson was one of Hefner's several girlfriends (Denise Truscello/WireImage)
Wilkinson was one of Hefner's several girlfriends (Denise Truscello/WireImage)

Asked how being a part of 'that environment' impacted her in the long run, she went on to confess that life in the mansion triggered 'unhealthy thoughts'.

"Not really settling for a marriage and stuff like that," she went on. "Which is not, I wouldn’t say unhealthy — I’m saying that everyone has their choices, and some people wanna be single, some people wanna be married.

"And I’m more of a fun idea type of person."

Wilkinson later claimed she 'manifested' herself a more conventional lifestyle. Following her departure from the Playboy Mansion, she married NFL player, Hank Baskett, with who she has two kids with, with the couple later getting divorced in 2018.

"I found myself so bored at the Playboy Mansion," she admitted. "I was just like, 'I’m ready to leave this place. I’m ready to start a family. I’m ready for the lifestyle: My kids go to a great school. I’m a soccer mom. I’m a softball mom. I’m a basketball mom'."

  • Former Playboy model Kendra Wilkinson who dated Hugh Hefner at 18 reveals why she’s no longer interested in men
  • Former Playboy Bunny Holly Madison reveals bizarre sex item Hugh Hefner used in shocking bedroom admission
  • Gordon Ramsay makes sad admission about relationship with rarely-seen brother
  • Playboy's Hugh Hefner is still giving strict instructions to his heirs from beyond the grave

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