Kendra Wilkinson revealed the one regret she has from her time living at the Playboy Mansion as one of Hugh Hefner’s girlfriends alongside Holly Madison and Bridget Marquardt.
“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, 39, told Fox News Digital in an interview published on Monday, June 11. “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.”
Wilkinson started her real estate career more than a decade after moving out of the Playboy Mansion in 2009. She passed her real estate exam in 2020, going on to document her new career on the docuseries Kendra Sells Hollywood between 2021 and 2023. (Kendra Sells Hollywood’s two seasons are now available to stream on Max.)
She joined Mauricio Umansky’s luxury real estate firm The Agency in 2020, before eventually making the jump to Douglas Elliman in October 2023.
Meanwhile, the Playboy Mansion went up for sale one year before Hefner’s death at age 97 in 2017. Hefner’s team originally asked $200 million for the historic Los Angeles home, but ultimately sold it for only $100 million to Daren Metropoulos in August 2016. (As part of the agreement, Hefner was allowed to live at the Playboy Mansion until his death.)
Wilkinson recently opened up about how her four-year relationship with Hefner impacted her sex life. She explained to Amy Robach and T.J. Holmes on their “Amy & T.J.” podcast that her time with Hefner contributed to her developing “unhealthy thoughts” about sex and marriage.
“Look, I struggle still to this day with my relationships and my views on sex,” she acknowledged in March.
Wilkinson was one of Hefner’s three girlfriends between 2004 and 2008, before going on to marry NFL star Hank Baskett at the Playboy Mansion in 2009. Baskett and Wilkinson had two children — son Hank, 15, and daughter Alijah, 10. (The former couple divorced in 2018.)
She told People in 2024 that her time at the Playboy Mansion “really messed” up her life and caused her to struggle for several years.
“It’s not easy to look back at my 20s. I’ve had to face my demons,” she said.
She added, “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.”
Wilkinson credited her hospitalization for panic attacks in September 2023 with getting her life back on track.
“[My doctors] got me on the right meds, and I feel like a million bucks tonight,” she said at this week’s 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. 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.”
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