
Her big regret has nothing to do with Hugh Hefner, but her own career ambitions at the time.
Kendra Wilkinson is sharing her one and only regret in her life -- and, yes, it has to do with her time living at the Playboy Mansion as one of Hugh Hefner's girlfriends.
In an interview with Fox News Digital this week, the 40-year-old reality star-turned-realtor shared what she wished she'd done sooner, while she lived with Hef from 2004 to 2009.
"The only thing I can say I regret in my life is not starting my real estate career while I was living at the Playboy Mansion," she stated.

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View Story"Like, I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking? But I'm now in real estate, so I'm good," she added.
The real estate agent started her current career more than 10 years she moved out in 2009, following the end of her five-year relationship with Hefner. She, Holly Madison and Bridget Marquardt became household names at the time, thanks to their reality show, The Girls Next Door.
Wilkinson quickly moved on with ex-husband Hank Baskett, having two kids with him before they later split as well.

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View StoryIn an interview last year with People, Wilkinson said her time at the Mansion "really messed" up her life and she left her feeling like she had no future.
"It's not easy to look back at my 20s. I've had to face my demons," she said. "It was the lowest place I've ever been in my life. I felt like I had no future. I couldn't see in front of my depression. I was giving up and I couldn't find the light. I had no hope."
In September 2023, Wilkinson was hospitalized for panic attacks, adding that the bulk of the trauma she's working through stems from her time with Hef.
"Why did I have sex with Hugh Hefner at that age? Why did I do that?" she said she asked herself. "Why did I go to the mansion in the first place? Why did I get big boobs? Why am I a sex symbol? Why did I bleach blonde my hair? Why did I do this to myself? Why did I?"

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View Story"[My doctors] got me on the right meds, and I feel like a million bucks tonight," she later said at an Operation Smile fundraiser.
"I feel amazing. They got me through it. We talked through it. I learned a lot about the brain and how we think, how we behave," she added.
"And it took a lot of opening my heart up, opening up my mind and really just dissecting everything that’s a part of me. And it took me a long time to heal and recover from a lot things."