Kendra Wilkinson is opening up about her relationship with Hugh Hefner and how it impacted her views on sex and relationships.
“Look, I struggle still to this day with my relationships and my views on sex,” Wilkinson, 39, told Amy Robach and T.J. Holmes on the Friday, March 20, episode of their “Amy & T.J.” podcast.
“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,’” she continued.
Wilkinson became one of Hefner’s main girlfriends in 2004, after meeting the Playboy founder at his 78th birthday party when she was 18. Shortly after their first encounter, Wilkinson moved into the famed Playboy mansion along with fellow girlfriends Holly Madison and Bridget Marquardt. She ended her relationship with Hefner in 2009.
Phillip Faraone/Getty Images Kendra Wilkinson is looking for love come 2025. “It’s time that I kind of evolve here and not stay in the booty call land,” Wilkinson, 39, admitted to Us Weekly exclusively at the 11th Annual American Reality Television Awards on Monday, November 18, at Avalon Hollywood. “It’s time I evolve and look […]
On Friday’s podcast episode, Holmes asked Wilkinson how her relationship with Hefner and “that environment” impacted her long-term.
“Again, you’re a teenager,” Holmes said. “You hadn’t been necessarily exposed to healthy relationships at that point in your life, but it puts 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?”
Hugh Hefner poses with Kendra Wilkinson, Bridget Marquardt, and Holly Madison. Carlo Allegri/Getty Images
Elaborating on her confession regarding her views on sex, Wilkinson admitted that her relationship with Hefner contributed to “just unhealthy thoughts.”
“Not really settling for a marriage and stuff like that,” she continued, ‘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.”
In 2016, Wilkinson admitted to cheating on Hefner during their five-year relationship and while living at the Playboy mansion
“I wasn’t there for romantic reasons and for marital reasons like Holly was,” the Kendra on Top star said while appearing on the “Kocktails With Khloe” podcast. “I had a great time.”
She continued, “I swear on my two kids — I never hooked up with one person in the mansion while being with Hef. I have that much respect. I would go to hotels down the street.”
After her relationship with Hefner, Wilkinson moved on and married former NFL player Hank Baskett in 2009. The pair went on to welcome two children — son Hank, 15, and daughter Alijah, 10 — before divorcing in 2018.
“I found myself so bored at the Playboy Mansion. 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,’” Wilkinson said of her decision to leave Hefner and settle down with Baskett. “I manifested it, and it came to me, and I met the perfect man, the man of my dreams.”
Wilkinson went on to describe her time with Baskett as the “happiest days of my entire life,” before detailing how devastating her divorce was emotionally.
“When those days came to an end, I crumbled so hard and it almost killed me,” she explained. “It almost killed me.”
After six years of therapy, Wilkinson — who now works in real estate – said that she’s now “living in the state of peace of mind.”
“You know, I’m on good meds,” she explained. I’m just in a really good place.”
