Kendra Wilkinson previously said Playboy ‘messed her whole life up’
Hugh Hefner’s ex-girlfriend Kendra Wilkinson has spoken about how her relationship with the Playboy founder left her with ‘a little bit of a sex problem’.
At just 18 years old, Wilkinson first set foot in the iconic Playboy Mansion, where she would go on to form a relationship with Playboy mogul Hugh Hefner when he was 78. She eventually moved into the mansion, sharing Hefner with his other two girlfriends, Holly Madison and Bridget Marquardt.
In a candid conversation on the Amy & T.J. Podcast, Wilkinson opened up about the complexities of their unconventional relationship and how it shaped her perspectives on intimacy and sex. She admitted, “I still struggle with my relationships and my views on sex to this day.”

“I had to go through a lot of therapy,” Wilkinson revealed, reflecting on her experiences. “They looked at me and said — this is the first time I’m admitting this — ‘You might have a little bit of a sex problem. You have a little bit of a problem when it comes to thinking about sex.’”
Host T.J. Holmes pressed Wilkinson further, asking how her relationship with Hefner, especially at such a young age, impacted her view of relationships. “You were a teenager,” he pointed out. “You hadn’t necessarily been exposed to healthy relationships. 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 kind of person you were drawn to?”
Wilkinson admitted it left her with “unhealthy thoughts,” particularly when it came to traditional ideas of settling down. “I didn’t really settle for marriage and stuff like that,” she explained. “But that’s not necessarily unhealthy — I think everyone has their own choices. Some people want to be single, some want to be married. I’m more of a ‘fun idea’ type of person.”

Wilkinson has opened up in the past about the deep reflection and support she sought years after leaving the Playboy Mansion. In a candid conversation with People, she revealed the struggles she faced during that time.
“I was trying to fight it on my own,” she confessed. “I was trying to cure it on my own, and you can’t do that. I was isolating, hiding, blaming myself, blaming the world.”
She explained how she was spiraling out of control, feeling like she wasn’t strong enough to survive. “I was in a dark place,” Wilkinson admitted.
Reflecting on how far she’s come, she shared: “A year ago, I was body-shaming myself. Now, I feel beautiful.” She clarified, “I’m not wild in the sense of taking my clothes off, partying, or drinking tequila, but I really faced myself and my demons. I feel like I’m the best mom I can be. I’m giving my kids everything I’ve got. I’m giving myself everything I’ve got.”
She added, “I’m so proud of myself for battling this and finding the solution, for getting the treatment I needed. It’s been a journey, and I’ve learned to embrace who I am.”