Kendra Wilkinson Reflects on Life, Regret, and Her Real Estate Journey
Kendra Wilkinson is opening up about her past — and the one big regret she carries from her Playboy days.
Speaking with Fox News Digital at the Operation Smile Fiesta in Los Angeles on June 3, the former Girls Next Door star got candid about her life, her career shift, and what she wishes she’d done differently while living in the Playboy Mansion.
“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,” the 39-year-old said with a laugh. “What was I thinking?”
Surrounded by celebrities and billionaires during her time at the mansion, Wilkinson now sees that period of her life as a missed opportunity to launch her future earlier. “I mean, I was surrounded by everyone… and what was I thinking?” she repeated. “But I’m now in real estate, so I’m good.”
Wilkinson’s journey has taken many turns since her time alongside Hugh Hefner. After years in the spotlight, she transitioned into real estate, passing her licensing exam in 2020 and launching the Max docu-series Kendra Sells Hollywood in 2021. The show gave fans a glimpse into her new career in luxury Los Angeles real estate. It ran for two seasons before wrapping in early 2024.
Though she briefly announced she was stepping away from real estate in 2024, citing mental health and family reasons, Wilkinson later admitted the announcement was premature.
“I just had a really bad day,” she told PEOPLE. “I should’ve never posted that I was quitting. I made a huge mistake.”
Now, she’s back in action — and busier than ever. “I have so many deals I’m working on right now,” she confirmed.
Beyond her career, Wilkinson has also shared emotional reflections on her past, including the challenges of overcoming the party-girl image she was known for during her Playboy years. One vulnerable moment came during Kendra Sells Hollywood, when she admitted to slipping back into old habits during a night out with clients.
“I feel sick as f—, not just from the hangover, but just not knowing what people really want from me,” she said. “People don’t want me as the real estate agent, they want me as the Playboy girl.”
Despite these struggles, Wilkinson continues to carve out her identity on her own terms — as a mother, a professional, and a woman who’s unafraid to own her story.
