Hugh Hefner’s former girlfriend Kendra Wilkinson has opened up about how her time with the Playboy mogul left her with “a bit of a sex issue.”
Wilkinson was just 18 when she first visited the iconic Playboy Mansion and eventually entered a relationship with Hefner, who was 78 at the time.
She later moved into the mansion, living alongside Hefner’s two other girlfriends, Holly Madison and Bridget Marquardt.
In a candid conversation on the Amy & T.J. podcast, Wilkinson reflected on how the relationship shaped her perception of sex and emotional connection.
She admitted, “Honestly, I still struggle to this day with relationships and how I view sex.”
Kendra (far left) shared Hugh Hefner with his other two girlfriends (Getty Images)
“I went through a lot of therapy, and they looked at me and said — and this is the first time I’m saying this — ‘You might be dealing with a bit of a sex issue. Your thoughts around sex might be something to explore.’”
Host T.J. Holmes also asked Wilkinson how her relationship with Hefner influenced her, especially since she was so young when it began.
He said: “You were still a teenager.
“You hadn’t really seen what a healthy relationship looks like at that stage in life, but it clearly set you on a path — how did that shape your ideas of love, relationships, and who you were drawn to?”
Wilkinson admitted it led to some ‘unhealthy thinking’.
She continued: “Not really believing in marriage and things like that.
“Which isn’t necessarily wrong — I mean, everyone’s different. Some prefer being single, others want marriage… I guess I’m more into the idea of fun and freedom.”
Kendra has previously spoken about her struggles (Instagram/@kendrawilkinson)
Wilkinson has been open about the deep reflection and support she sought years after leaving the Playboy Mansion.
In an interview with People, she shared candid details about her personal battles.
“I tried to handle it all alone,” she admitted. “I thought I could fix it myself, but that’s just not how it works. I shut myself off, hid away, blamed myself and everything around me.”
“I was in a downward spiral and truly felt like I didn’t have the strength to make it through.”
“Just a year ago, I was picking apart my body. Today, I feel beautiful,” she said. “I’m not wild in the sense of partying, stripping down, or downing shots of tequila anymore—I’ve faced who I really am and dealt with the darkness inside.”
“I genuinely feel like I’m the best mom I can be. I’m giving everything I have to my kids—and to myself.”
“I’m incredibly proud for fighting through it, finding real answers, and getting the help I needed.”
