You probably remember Kendra Wilkinson from her days on The Girls Next Door, where she lived the high life inside the Playboy Mansion. Now 40 and a successful real estate agent, Wilkinson is opening up about what she truly regrets from that chapter in her life. It’s not the flashy lifestyle, the cameras, or even Hugh Hefner himself. It’s something far more personal and tied to her career dreams that were delayed far too long.
Wishing She’d Started Sooner In Real Estate
While speaking with Fox News Digital, Wilkinson admitted that she has only one regret about her time living in the iconic mansion. From 2004 to 2009, she lived there as one of Hefner’s girlfriends and a reality TV star. Looking back, she realizes she missed an opportunity to kickstart the career she loves now. “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 during the interview.
She elaborated on that thought, explaining how she had endless networking opportunities during that time. “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,” she added. The regret isn’t rooted in scandal or drama—it’s grounded in a wish that she had focused on her future earlier. For Wilkinson, that one decision feels like a missed chance to build something lasting during her high-profile years.
The Long Road To Building A New Life
More than a decade passed between her departure from the mansion and her decision to begin a real estate career. Wilkinson moved out in 2009 after ending her five-year relationship with Hefner. That same year, she transitioned from reality TV girlfriend to wife and mother. She married former NFL player Hank Baskett and had two children. While she moved on from the mansion physically, the emotional impact stayed with her far longer. It took years for her to fully reclaim her identity.
Her fame skyrocketed alongside Holly Madison and Bridget Marquardt thanks to The Girls Next Door. But when the cameras stopped rolling, the aftereffects of that life became more complicated than anyone might have guessed. Instead of riding a smooth wave into the next phase of her life, Wilkinson found herself grappling with questions about her worth and her future. That struggle became even more apparent during interviews where she spoke openly about her lowest moments.
Facing Darkness After The Cameras Stopped
In a 2023 interview with People, Wilkinson didn’t hold back when describing how hard it was to look back at her 20s. “It’s not easy to look back at my 20s. I’ve had to face my demons,” she admitted. She described that period as the lowest she’s ever been, revealing just how much emotional weight she carried after leaving the Playboy Mansion. “It was the lowest place I’ve ever been in my life. I felt like I had no future. I couldn’t see in front of my depression. I was giving up and I couldn’t find the light. I had no hope,” she explained.
These weren’t just passing emotions. The pain ran deep, and it continued to affect her for years. Even with her career and family life moving forward, Wilkinson struggled with unresolved trauma from her time at the mansion. Her reflections show a woman who isn’t afraid to speak truthfully about mental health. It’s clear that the glitz and glamour masked something darker—something that took years of introspection and healing to begin untangling.
Health Scare Leads To Breakthrough And Healing
By September 2023, the weight of her emotional struggles reached a boiling point. Wilkinson was hospitalized for panic attacks, a wake-up call she couldn’t ignore. She revealed that most of the trauma she’s been working through stems directly from her years with Hugh Hefner. “Why did I have sex with Hugh Hefner at that age? Why did I do that?” she said she asked herself. She also questioned her choices around body image and her public persona. “Why did I go to the mansion in the first place? Why did I get big boobs? Why am I a sex symbol? Why did I bleach blonde my hair? Why did I do this to myself? Why did I?”
These aren’t rhetorical questions. They’re the reflections of someone doing deep internal work. Wilkinson shared her thoughts publicly, not for shock value, but to shine a light on the hard truths behind fame. At an Operation Smile fundraiser, she spoke honestly about how therapy and the right medication finally brought relief. “[My doctors] got me on the right meds, and I feel like a million bucks tonight,” she said with gratitude.
Learning To Rebuild From The Inside Out
Wilkinson didn’t stop at just feeling better. She dove into understanding herself on a deeper level. “I feel amazing. They got me through it. We talked through it. I learned a lot about the brain and how we think, how we behave,” she said. Her journey has involved not just medication but real conversations about identity, purpose, and healing. “And it took a lot of opening my heart up, opening up my mind and really just dissecting everything that’s a part of me. And it took me a long time to heal and recover from a lot of things,” she added.
You can sense the transformation in her words. Wilkinson has gone from questioning every past decision to finally feeling grounded in who she is now. Her path hasn’t been perfect, but it’s honest. You see someone who’s learning to forgive herself, move forward, and build something lasting—not from a TV show or a magazine cover, but from within. That’s a story worth paying attention to.
Do you think it’s ever too late to start over and reclaim your story? Let us know in the comments on Facebook.
Via: toofab.
