Former Playmate Kendra Wilkinson Confesses She 'Still Struggles with Relationships' After Dating Playboy Mogul Hugh Hefner
Kendra Wilkinson admitted she had a 'sex problem' after her relationship with Hugh Hefner.
April 10 2025, Published 6:30 p.m. ET
Former Playmate and reality star Kendra Wilkinson has confessed she "still struggles with relationships" after dating Hugh Hefner in her early 20s, RadarOnline.com can reveal.
Wilkinson, 39, confessed she went through a period of time when she had "a bit of a sex problem" after dating Hefner, who was 60 years her senior.
Wilkinson started dating Hefner when she was 18-years-old.
Eight years after the Playboy founder died at aged 91 from sepsis brought on by E. coli, Wilkinson opened up about the trauma she continues to unpack after living with Hefner in the Playboy mansion for five years.
Wilkinson first met Hefner when she was 18-years-old. She was hired to be a "painted girl" at his 78th birthday party in April 2004.
She eventually moved into his infamous Tudor-style mansion in Los Angeles alongside fellow live-in girlfriends Holly Madison and Bridget Marquardt. The trio of girlfriends starred in E! reality show The Girls Next Door, which ran for six seasons.
Wilkinson lived in the Playboy mansion for five years alongside fellow girlfriends Holly Madison and Bridget Marquardt.
While Wilkinson ended her relationship with Hefner when she was 23-years-old in 2009 – and moved out of the mansion that same year – she candidly revealed she "still struggles" with intimacy to this day.
During an appearance on Amy Robach and T.J. Holmes' Amy & T.J. podcast, Wilkinson confessed: "Look, I struggle still to this day with my relationships and my views on sex."
She went on to explain how therapy helped her work through her intimacy issues.
Wilkinson said: "I had to go through a lot of therapy, and 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."
Holmes then asked Wilkinson how living in the Playboy mansion impacted her.
Wilkinson said she 'had to go through a lot of therapy' after the breakup.
He asked: "Again, you're a teenager. You hadn't been necessarily exposed to healthy relationships at that point in your life, but it put you on a certain path — what did that do to you and (how did it) shape what you thought a relationship was, should be and the type of person you were interested in?"
Wilkinson said her time in the mansion with Hefner caused her to have "unhealthy thoughts."
She elaborated: "Not really settling for a marriage and stuff like that. 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."
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The former Playmate said she had 'deep regret' over dating Hefner.
This isn't the first time Wilkinson has opened up about her relationship with Hefner.
In an interview with People, the former reality star confessed she had "deep regret" over the relationship – and began questioning why she slept with the magazine mogul.
She told the outlet: "I got into deep regret (afterwards). I got to that point where I started hating myself (and asking), 'Why did I have sex with Hugh Hefner?' I hated my boobs, my body, my face. I got to that point where I started hating myself."
Wilkinson – who was hospitalized, diagnosed with anxiety and prescribed antipsychotic medications in 2023 – admitted her time in the mansion "messed up her whole life," adding: "It's not easy to look back at my 20s. I've had to face my demons."
