She seemed to do the "sex" thing all right. I'm always the last to know.
Playboy model Kendra Wilkinson says she has a ‘sex problem’ after Hugh Hefner relationship with 60-year age gap
By Alexandra Bellusci
Published March 22, 2025, 4:02 p.m. ET
Kendra Wilkinson is sharing a confession about her days romancing Playboy’s late kingpin.
“The Girls Next Door” alum got candid about her past relationship with Hugh Hefner and how it impacted her views on intimacy.
“Look, I struggle still to this day with my relationships and my views on sex,” Wilkinson, 39, said on Friday’s episode of the “Amy & T.J.” podcast.
Playmate Holly Madison, publisher Hugh Hefner, playmate Bridget Marquardt and playmate Kendra Wilkinson. Hugh Hefner poses with Playboy Models.
“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 confessed.
Wilkinson became one of Hefner’s girlfriends after the two met at his 78th birthday party when she was just 18 in 2004.
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The reality television star then moved into the Playboy Mansion with Hefner’s other girlfriends Holly Madison and Bridget Marquardt. Wilkinson lived there for five years until she called it quits with Hefner in 2009.
Host T.J. Holmes asked the “Kendra on Top” star how dating Hefner and being a part of “that environment” impacted her in the long run.
“Again, you’re a teenager,” the former news anchor 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?”
Wilkinson confessed that it caused her to have “just unhealthy thoughts.”
“Not really settling for a marriage and stuff like that,” she expanded, ‘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 revealed she was unfaithful to Hefner during their relationship.
“I wasn’t there for romantic reasons and for marital reasons like Holly was,” she said while on the “Kocktails With Khloe” podcast at the time. “I had a great time.”
Added Wilkinson, “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.”
The model went on to tie the knot with former football player Hank Baskett in 2009 and the pair share son Hank, 15, and daughter Alijah, 10. Baskett and Wilkinson divorced 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 told Holmes and cohost Amy Robach. “I manifested it, and it came to me, and I met the perfect man, the man of my dreams.”
To this day, Wilkinson likes to look at her time as a wife and a mother as the “the golden years.”
“When those days came to an end, I crumbled so hard and it almost killed me,” she explained. “It almost killed me.”
Despite the cheating scandal that broke the real estate agent and athlete up, the two still have a great co-parenting relationship.
As Wilkinson put it, “Even though we’re divorced, he’s the father of my kids and he’s the most amazing father to my kids, and I know I chose right with him.”
After six years of therapy, Wilkinson was happy to share she now lives “in the state of peace of mind.”
“You know, I’m on good meds,” she gushed. I’m just in a really good place.”
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