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Kendra Wilkinson Spills the Tea on Her One Regret from Playboy Mansion Days

Kendra Wilkinson Spills the Tea on Her One Regret from Playboy Mansion Days
  • PublishedJune 11, 2025

Okay, so let me tell you—this is WILD! Kendra Wilkinson, the Playboy model turned realtor, is dishing out some major tea on her time living at the iconic Playboy Mansion with Hugh Hefner. I mean, can you even imagine having a front-row seat to all the glamour and drama that came with being one of Hef’s girlfriends? Kendra’s got some serious regrets, but not about the experiences she had or the connections she made—nope, it’s all about not jumping into the real estate game sooner!

According to Kendra, she told Fox News on June 3 that her one regret in life is not starting her real estate career while she was living at the Playboy Mansion. I mean, think about it—she was surrounded by A-list celebrities, billionaires, and who knows who else! It’s like having a golden ticket to networking heaven, and she didn’t cash in on it. “What was I thinking? I was surrounded by everyone—every celebrity, every billionaire,” she said, basically kicking herself for not being more proactive.

But here’s the thing: Kendra’s not bitter about her time at the Playboy Mansion. In fact, she describes it as a “heavenly experience.” She gushes about her relationship with Hugh, saying he was a “generous, nice person” who always treated her well. However, her Girls Next Door costar Holly Madison can’t say the same. Holly opened up about her own experiences with Hugh in 2023, revealing that she was “shell shocked” after leaving the relationship and realizing her vision of him was just a fantasy.

Now, let’s get back to Kendra’s real estate career. After getting her license in 2021, she launched her own Discovery+ series, Kendra Sells Hollywood. It’s like she finally cashed in on those connections she made at the Playboy Mansion! But what about her other costars? Bridget Marquardt is killing it with her paranormal-themed podcast, Ghost Bunny, and hosting the Girls Next Level podcast with Holly. And Holly? She’s been busy competing on Dancing with the Stars and publishing a memoir about her time in the Playboy Mansion.

As I wrap up this juicy gossip session, I’ve got to say: Kendra’s story is a major reminder that it’s never too late to pursue your passions. And who knows? Maybe she’ll sell a mansion or two to a certain A-list celebrity. The possibilities are endless, and I’m here for it! Okay, I need to calm down after that—it’s been a wild ride spilling all this tea!

Sources: Celebrity Storm and E! Online, Fox News, People Magazine
Attribution: Creative Commons Licensed

Written By
Quinn Parker