Kendra Wilkinson Reveals Her One Regret About Living in the Playboy Mansion With Hugh Hefner: 'What Was I Thinking?'

Kendra Wilkinson opened up about the one thing she wishes she had done differently during her time with Hugh Hefner.

“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 Girls Next Door alum revealed at the Operation Smile 25th Los Angeles Smile Fiesta red carpet on June 3.

“What was I thinking?” she said. “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.”

This isn’t the first time Wilkinson has reflected on how her past shaped her future.

“Was I sexualized? Absolutely,” she shared during a past interview on the "I Do, Part 2" podcast. “Did that cause me problems later in life? Absolutely. So, you know, choices — there are consequences for every choice you make.”

Wilkinson got even more candid, revealing how her views on intimacy have been affected ever since.

“I struggle still to this day with my relationships and my views on s--,” she explained. “And I had to go through a lot of therapy… and they looked at me and they're like — this is the first time I'm admitting this — but they're like, ‘You might have, like, a little bit of a s-- problem. Like, you have a little bit of a problem when it comes to thinking of s--.’”

The former Playboy Bunny said those issues often come from “unhealthy thoughts” that don’t really fit into a committed marriage or long-term relationship.

Still, she’s always been open about the fact that her time with Hefner gave her something she was missing in her younger years.

Wilkinson said Hefner gave her a sense of security.

“I can honestly look back and say that I was safer at the Playboy mansion than I was at 15 years old dealing drugs,” she said. “So in that case, I was safe. I was in a safe environment. I was healthy, eating salads every day, working out every day, no drugs every day.”

Wilkinson eventually moved out in 2009 and married former NFL player Hank Baskett. The couple, who divorced in 2018, share two children.

“I left the Playboy mansion at age 23, got pregnant, got married at the age of 23, then started my life as a wife and a mother,” she said. “And it was the golden years of my life.”

Looking back, Wilkinson said she was eager for a change.

“I found myself just, you know, so bored at the Playboy mansion. I was just like, ‘I’m ready to leave this place. I’m ready to start a family,’” she recalled.

Wilkinson turned her life around when she passed the California real estate exam in June 2020. Just a month later, she joined The Agency — the luxury real estate firm founded by Mauricio Umansky.