Kendra Wilkinson has one regret from her Playboy days — and it’s not what you’d expect.
The former Playboy Bunny and Girls Next Door star, now 40, says she wishes she’d started her real estate career back when she was living at the Mansion with Hugh Hefner, Holly Madison, and Bridget Marquardt between 2004 and 2008.

“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,” Wilkinson told reporters. “I mean, I was surrounded by everyone — every celebrity, every billionaire. What was I thinking?”
After leaving Playboy behind, Wilkinson reinvented herself as a realtor, launching her new career in 2020 after passing California’s real estate exam. Her transition into the industry has been documented on Kendra Sells Hollywood, where she’s seen building a name for herself in the luxury market.

The move marks a full circle moment for a woman who once said Playboy “messed up my whole life.” In a 2024 interview with People, Wilkinson revealed she suffered a severe breakdown the previous year, saying she “spiraled into psychosis” and felt she was “at death’s door.”
The former reality TV star has since stabilized, crediting her work in real estate for grounding her after years in the public eye. “I’m good now,” she said. “Real estate saved me.”
For Wilkinson, the regret isn’t about fame or Hefner or lost youth — it’s about not recognizing opportunity when it was right in front of her.
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Last modified: October 16, 2025