Kendra Wilkinson Reveals the One Thing She Regrets About Life at the Playboy Mansion

When people reflect on chapters of their lives, it's often with a mix of pride, nostalgia, and the occasional "what if." That’s exactly the tone Kendra Wilkinson struck in a recent interview where she opened up about one missed opportunity that still lingers in the back of her mind.

Kendra Wilkinson is no stranger to the spotlight. For several years in the early 2000s, she was a fixture at the Playboy Mansion, one of Hugh Hefner’s girlfriends and a familiar face on the reality series The Girls Next Door.

While others came and went, Wilkinson became one of the more recognizable names associated with that era of the Mansion’s history. Her time there lasted from 2004 to 2009, years marked by celebrity events, media appearances, and an unconventional lifestyle that captivated the public.

But now, at 39, Wilkinson is looking back with some perspective. In a recent chat with Fox News Digital, she spoke candidly about the one thing she wishes she’d done differently while living in one of the most talked-about houses in America.

“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 said. “What was I thinking? I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking?”

She began dating Hugh Hefner at 18, while he was 78.

It’s an honest reflection, and one that feels grounded. At a time when she had access to some of the most connected people in entertainment and business, Wilkinson admits she didn’t fully take advantage of the environment. But there’s no bitterness in her tone, more of a shrugging acknowledgment that she missed a chance, not a full-blown lament.

Since leaving that world behind, Wilkinson has made her way into real estate, carving out a career in a completely different field. And by all accounts, she’s been good at it. She’s worked on high-level deals and made a name for herself beyond the shadow of the Playboy Mansion. That said, the road hasn’t always been smooth.

In May 2023, she briefly announced she was stepping away from real estate altogether. But in hindsight, she admits it wasn’t her best moment.

“I just had a really bad day,” she told People. “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.”

Kendra Wilkinson lived in the mansion for five years.

The admission is classic Wilkinson, unfiltered and willing to laugh at herself. Even when people appear to have it all figured out sometimes, they’re still navigating rough days like anyone else.

Looking back on her years at the Mansion, Wilkinson doesn’t shy away from the complicated reality of that time. On one podcast, she described her life there as "heaven," but also noted that it wasn’t always as glamorous as it seemed from the outside.

She shared that she often felt isolated, saying she didn’t have many close friendships during that time, aside from one other woman. Her daily routine was surprisingly quiet: working out, going for runs, taking spin classes, and thinking ahead to the next party.

“All I did was work out and eat. I would be preparing for the next party or something, like, ‘What am I going to wear?’ That took a week out of the time,” she said. “It was just like heaven. It was a heavenly experience for me. Like there couldn't have been a better experience.”Instagram

It’s an interesting contrast, feeling lonely in a place she still describes as idyllic. That blend of glamour and emptiness seems to define much of what people imagine life at the Playboy Mansion might have been like.

Wilkinson doesn’t pretend it was anything else. She enjoyed it for what it was, regretted what she didn’t do, and moved on.

Her story is one of reinvention. From reality TV to real estate, with a few personal stumbles along the way, she’s still finding her footing, but doing it on her terms now.

And maybe that’s the real takeaway: it's never too late to start something new, even if the timing wasn’t perfect the first time around.