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Kendra Wilkinson reveals her biggest regret about living in the Playboy Mansion

Kendra Wilkinson reveals her biggest regret about living in the Playboy Mansion

Daily Mail​12-06-2025

Kendra Wilkinson often reflects on moving into the Playboy Mansion at the tender age of 18.
In 2004 the star — who turns 40 on Thursday — moved from San Diego to Los Angeles to become one of Hugh Hefner's three live-in girlfriends alongside Holly Madison and Bridget Marquardt.
Speaking with Fox News Digital this week, the blonde bombshell revealed the one regret she has about her four years in the sprawling abode.
'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,' she told the outlet.
Wilkinson explained, '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.'
Wilkinson rose to fame on the E! unscripted series The Girls Next Door, which followed her life as one of Hefner's girlfriends.
The show lasted for six seasons between 2005 and 2010 and she lived at the famous estate from 2004-2009.
She began her real estate career when she got her license in 2020 and joined fellow reality star realtor Mauricio Umansky's The Agency.
A docuseries, dubbed Kendra Sells Hollywood on Discovery+, showcased her struggle as a new agent in the bustling industry.
It lasted for two seasons from 2021-2023.
The star told People last November that she was 'off mentally' while filming the show.
'I feel a little regret filming my last show because I wasn't really ready,' she confessed at the time. 'I was a little off mentally and I wasn't prepared to be on a camera just yet. I wasn't fully healed or there yet. Now I feel there.'
Kendra was married to her ex-husband, former NFL star Hank Baskett, from 2009 to 2018.
They share two children: son Hank Baskett IV, 15, and daughter Alijah, 11.
Speaking with Amy Robach and T.J. Holmes on their self-titled podcast in March, the blonde bombshell referred to her time being married as the 'happiest days of my entire life.'
'And so when those days came to an end, I crumbled so hard, and it almost killed me. It almost killed me,' she emphasized.
Kendra elaborated: '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, and it was the golden years of my life.'
Looking back at her choice to settle down with Hank, she affirmed: 'It was the right timing. I found myself so bored at the Playboy Mansion. I was just like, 'I'm ready to leave this place. I'm ready to start a family. I'm ready for the lifestyle: My kids go to a great school. I'm a soccer mom. I'm a softball mom. I'm a basketball mom.''
She added, 'I manifested it, and it came to me, and I met the perfect man, the man of my dreams.'
And Kendra heaped praise on her ex, noting, 'Even though we're divorced, he's the father of my kids and he's the most amazing father to my kids, and I know I chose right with him.'

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