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Hugh Hefner's ex-girlfriend Kendra Wilkinson opens up about her one regret from Playboy Mansion

Home> Celebrity> News

Published 19:39 11 Jun 2025 GMT+1

Hugh Hefner's ex-girlfriend Kendra Wilkinson opens up about her one regret from Playboy Mansion

Kendra Wilkinson spent five years in the Playboy Mansion in the early 2000s

Callum Jones

Callum Jones

Hugh Hefner's former girlfriend Kendra Wilkinson has opened up about the one regret she's had since leaving the Playboy Mansion.

While the infamous mansion has seen many people come and go, there were some women who were very much mainstays.

Wilkinson was one of those to have spent a lot of time in the Los Angeles residence, and has certainly had a lot of stories to tell about it since Hefner passed away aged 91 in 2017.

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The 39-year-old was one of the Playboy founder's girlfriends between the years of 2004 and 2009, and, in a recent interview, has opened up on some of the opportunities she missed and ultimately regrets during that time.

Kendra Wilkinson spent five years in the mansion (Jesse Grant/Variety via Getty Images)
Kendra Wilkinson spent five years in the mansion (Jesse Grant/Variety via Getty Images)

Speaking to Fox News Digital, Wilkinson said: "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? 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."

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While she may have some regrets, Wilkinson has excelled in her real estate career ever since, having worked in various high-up roles before leaving the industry for pastures new in 2023.

Wilkinson made that announcement in May of that year, though later confirmed she would't be leaving the business after all.

She told People in 2023: "I just had a really bad day. 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.

"But I’m back in it. I have so many deals I’m working on right now."

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She started dating Hugh Hefner when she was 18 and he was 78 (Gregg DeGuire/WireImage)
She started dating Hugh Hefner when she was 18 and he was 78 (Gregg DeGuire/WireImage)

During an appearance on The Skinny Confidential Him & Her Podcast recently, Wilkinson reflected on her time in the mansion as 'heaven'.

Noting she felt 'left out' and 'didn't have friends' other than one other girl, she explained her typical day-to-day was 'working out' a lot and 'running,' going to the 'canyon' and doing 'spin class'.

Wilkinson continued: "All I did was work to and eat, work out, eat. I would be like preparing for the next party or something, 'What am I going to wear'. That took a week out of the time.

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"What else? It was just like heaven. It was a heavenly experience for me. Like there couldn't have been a better experience."

Featured Image Credit: Denise Truscello/WireImage

Topics: Hugh Hefner, Celebrity

Callum Jones
Callum Jones

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