Kendra Wilkinson unplugged: tales from the Playboy Mansion to finding her true self

IOL News

20-05-2025

In happier times, Playboy magazine's late founder, Hugh Hefner, with Kendra Wilkinson.
Image: Instagram.
Kendra Wilkinson, a former Playboy model, recently shared her experiences as one of Hugh Hefner's girlfriends on "The Skinny Confidential".
During the interview, she discussed the realities of life at the Playboy Mansion, her transition to being single, and her journey of self-discovery.
Now a realtor, television personality, model and author, Wilkinson first captured the spotlight on the hit reality show "The Girls Next Door", which showcased life inside the Playboy Mansion.
Wilkinson, who has also successfully starred in her own series "Kendra" and "Kendra On Top", reflected on how her commitment to authenticity has been the cornerstone of her two-decade long career.
"I've always been this party girl, and who says it like it is. I wear my heart on my sleeve as well, which sometimes comes at a cost."
Having been single now for seven years since her divorce from Hank Baskett, Wilkinson candidly spoke about the difficulties of dating: "I've been divorced and single for seven years now. I've explored little things here and there, but I have not been in a relationship.
"It's going to take a lot to be my boyfriend now. I am not settling for whatever. I'm so used to being single ... Now I look at men and freak out thinking about commitment ... I get really nervous about life getting boring."
Wilkinson admitted that while she does struggle with shame and regret, at the time she chose to enter the Playboy Mansion, she was faced with difficult choices in her life.
"I was 18 at the time. It was either I was going to be a stripper or take this one-way ticket to LA and move into the Playboy Mansion ... those were the only two options I had, and I knew myself, I knew I could survive, so I took the trip to LA and never looked back."
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Wilkinson expressed gratitude for her time at the Mansion, describing it as a "safe and healthy environment", highlighting that, contrary to public perception, life there was not as scandalous as it seemed.
"It was so amazing, and it was healthy for me, it was happy for me, I was safe, and it's taboo to the world because they don't really know what went on there. In my perspective, it was only one party every few months, and the rest was that we all had sex with Hugh Hefner once a week, and that's the taboo, that we had sex with a 70/80-year-old."
"I had room service 24/7. I could eat whatever I wanted, I could eat healthy, I had chefs making me salad every day. Anything I wanted, I got. The parties were fun, I've been to worse parties outside the mansion than I ever did at the mansion. I couldn't have been happier."
Wilkinson's insights into her life were not limited to her time in the Mansion; she also spoke on how she began preparing for her future.
"I started setting myself up. I started booking my own work, and I hustled my a** of to get my new show, to book appearances around the world. I had issues with the business part of it, but not Hugh. He was a generous, nice person."
Looking ahead, Wilkinson, who has a ten-year-old daughter, says that she has made sure that her daughter will never have to make those hard choices like she did growing up.
"She's 10 and I already told her that she's going to college."
Watch the full episode below.