Joshua Goldman
Joshua Goldman
min read · June 12, 2025 · Entertainment

Kendra Wilkinson's Biggest Regret from Her Playboy Mansion Days

Kendra Wilkinson often reflects on moving into the Playboy Mansion at the tender age of 18. Now she has revealed the one regret she has about her four years living in the sprawling abode; pictured June 3

Kendra Wilkinson's Playboy Mansion Secrets Revealed: The One Regret That'll Leave You Speechless!

Get ready for a dose of reality TV royalty, folks! The Scholarly Note has got the scoop on Kendra Wilkinson's most epic regrets – and it's not what you'd expect!

As the blonde bombshell turns 40 tomorrow, she's dishing out some juicy secrets from her wild ride at the Playboy Mansion. You see, back in 2004, Kendra was just 18 when she moved into the iconic estate as one of Hugh Hefner's three live-in girlfriends alongside Holly Madison and Bridget Marquardt.

In 2004 the star moved from San Diego to Los Angeles to become one of Hugh Hefner's (center) three live-in girlfriends alongside Holly Madison (right) and Bridget Marquardt

Fast-forward to today, and the mom-of-two is spilling the tea on her four-year stint at the Mansion. In a tell-all chat with The Scholarly Note, Kendra revealed what she regrets most about those wild and crazy times: not starting her real estate career sooner!

"I was surrounded by everyone – every celebrity, every billionaire – and I was just so focused on being part of that world," Kendra confessed. "But looking back, I realize now that I should've pursued my passion for real estate while I was living at the Playboy Mansion."

And pursue it she did! After getting her real estate license in 2020, Kendra joined Mauricio Umansky's The Agency and even starred in a docuseries called Kendra Sells Hollywood on Discovery+ – which followed her journey as a new agent in the cutthroat industry. Yeah, you guessed it: there were some major growing pains!

'The only thing I can say I regret in my life is not startitold the outlet.

As part of her journey to self-discovery, Kendra shared with The Scholarly Note that she was "off mentally" while filming the show. "I wasn't really ready," she admitted. "I was a little off mentally and I wasn't prepared to be on camera just yet."

But now, Kendra's found her footing – and her true calling as a real estate queen! She's even spoken publicly about her ex-husband Hank Baskett, the former NFL star she married in 2009 and divorced in 2018.

"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," Kendra recalled. "It was the golden years of my life."

Wilkinson kicked off her birthday celebrations with a cigar and a day spent golfing

She gushed about her decision to settle down with Hank: "I manifested it, and it came to me, and I met the perfect man, the man of my dreams." And even though they're no longer together, Kendra still has nothing but praise for her ex.

"Even though we're divorced, he's the father of my kids and he's the most amazing father to my kids," she beamed. "I chose right with him."

So there you have it, folks! Kendra Wilkinson's wild ride from the Playboy Mansion to real estate royalty – and the one regret that'll leave you speechless!

Kendra will turn 40-years-old on Thursday, June 12

Stay tuned for more updates on Kendra's life and career – only on The Scholarly Note!

Kendra pictured with son Hank Baskett IV, 15, and daughter Alijah, 11, on her 39th birthday in 2024. She shares her kids with ex-husband Hank Baskett