Kendra Wilkinson Reveals Her One Regret from Her Playboy Past

Published: June 10, 2025

Kendra Wilkinson, the former Playboy star and girlfriend of Hugh Hefner, has opened up about her past and revealed her one and only regret.

During an interview with Fox News Digital at Operation Smile Fiesta, Wilkinson, 39, reflected on her time at the Playboy Mansion and her current career in real estate.

"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. What was I thinking?" Wilkinson said with a laugh. "I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking?"

Kendra Sells Hollywood, which ended in 2023 after two seasons.

In recent years, Wilkinson has also reflected on other aspects of her time in the Playboy Mansion. One particularly emotional instance came during the first season of Kendra Sells Hollywood.

After partying hard with some potential buyers, Wilkinson said in a confessional that she "slipped back to the old Kendra I used to be and there was a price to pay for that."

"I feel sick as f---, not just from the hangover, but just not knowing what people really want from me," she later added. "I don't feel like I can trust anyone. People don't want me as the real estate agent, they want me as a good time at parties, that celebrity — the Playboy girl."

Wilkinson has lived a very different life since her Playboy days. She began her real estate career in 2020 and has continued to speak out about her experiences.

In 2024, Wilkinson announced her departure from real estate, citing her mental health and family. However, she later revealed that she made a premature announcement and did not actually quit.

Wilkinson has continued to speak out about her experiences living in the Playboy Mansion, including a particularly emotional instance during the first season of Kendra Sells Hollywood.