Kendra Wilkinson Reveals the 1 Regret She Has from Her ‘Playboy’ Past

Kendra Wilkinson only has one regret.

The former Playboy star and girlfriend of Hugh Hefner, who died in September 2017, got candid about her past while speaking with Fox News Digital at Operation Smile Fiesta, hosted at Los Angeles’ Candela La Brea, on June 3.

“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?” the real estate agent, 39, said with a laugh.

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“I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking?” she added. “But I’m now in real estate, so I’m good.”

Kendra Wilkinson has lived a very different life since her Playboy days.

It’s been two decades since Wilkinson lived in the Playboy Mansion and co-starred in Girls Next Door with Holly Madison and Bridget Marquardt. She began her real estate career much more recently, after passing her real estate exam in 2020.

Wilkinson went on to document her new career in the Max series Kendra Sells Hollywood, which saw her try to make a name for herself in the high-stakes world of luxury Los Angeles real estate. The show premiered in November 2021 and came to a close after two seasons, Wilkinson confirmed to PEOPLE in January 2024.

After four years in the field, Wilkinson announced her departure from real estate in 2024, citing her mental health and family. (The star shares two kids, daughter Alijah, 11, and son Hank IV, 15, with ex-husband Hank Baskett.)

But the former Playboy star did not actually call it quits, she later revealed exclusively to PEOPLE. Rather, she made a premature announcement.

“I just had a really bad day,” she told PEOPLE in 2024. “So I did announce that I’d be stepping away from real estate, but that was just a really bad day in my life and I should’ve never probably Instagrammed that I’m quitting, but I did on accident like an idiot so I made a huge mistake.”

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“But I’m back in it,” she clarified. “I have so many deals I’m working on right now.”

Kendra Wilkinson has continued to speak out about her experiences living in the Playboy Mansion.

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, the star 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.”