Former Playboy model Kendra Wilkinson has one regret from her time at Hugh Hefner’s mansion, a revelation that has captured headlines and sparked conversations about personal growth and missed opportunities. In a recent interview, Wilkinson, now a real estate agent and reality TV star, opened up about her biggest life regret: not launching her real estate career while she lived at the iconic Playboy Mansion. This candid admission, made on the red carpet at the Operation Smile 25th Los Angeles Smile Fiesta, highlights how Wilkinson views her past experiences through a lens of both gratitude and self-reflection.
Wilkinson, who lived in the mansion from 2004 to 2009 as one of Hefner’s girlfriends, reflected on the unique environment she was exposed to—surrounded by celebrities, billionaires, and endless networking possibilities. “What was I thinking?” she mused, laughing at her younger self. “I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking?” Now, as a successful real estate agent, Wilkinson looks back and wishes she had seized those opportunities earlier.
Her story is not just about regret, but also about resilience and reinvention. After leaving the mansion, Wilkinson faced her share of personal struggles, including a highly publicized divorce and mental health challenges. Yet, she has consistently found ways to reinvent herself, proving that it’s never too late to pursue new dreams.
The Playboy Mansion Years: A Mixed Legacy
Kendra Wilkinson’s time at the Playboy Mansion was a defining chapter in her life. She entered the mansion at just 18 years old, faced with limited choices and a desire to escape a difficult situation. Wilkinson has described her decision as a survival move: “It was either I was going to be a stripper or take this one-way ticket to LA and move into the Playboy Mansion… those were the only two options I had, and I knew myself, I knew I could survive.”
Contrary to popular belief, Wilkinson remembers her years at the mansion as a mostly positive experience. She describes it as a safe and healthy environment, where she had access to room service, private chefs, and a supportive community. “It was so amazing, and it was healthy for me, it was happy for me, I was safe,” she recalls. The parties, while legendary, were not as frequent or scandalous as the public imagined—Wilkinson notes there was only one major party every few months, with the rest of the time spent in a more relaxed, almost familial atmosphere.
Yet, the mansion was not without its emotional toll. Wilkinson has admitted to struggling with shame and regret, especially regarding the choices she made at such a young age. She has also spoken openly about the impact of reality TV fame and the paparazzi, which left her with lingering PTSD and self-esteem issues. Still, she insists that she does not regret her time at the mansion itself, only the way certain aspects of her life and career unfolded afterward.
Kendra Wilkinson’s Real Estate Regret: A Missed Opportunity
The one regret that stands out most for Kendra Wilkinson is not starting her real estate career while she lived at the Playboy Mansion. Looking back, she sees the mansion as a golden opportunity to network and build a foundation for a future career. Surrounded by Hollywood’s elite, she could have leveraged those connections much earlier.
Wilkinson did eventually enter the real estate world, passing the California real estate exam in 2020 and joining The Agency, a luxury real estate firm. She later moved to Douglas Elliman, another high-profile agency, and even starred in her own reality series, “Kendra Sells Hollywood,” which ran for two seasons. The show documented her journey as she navigated the ultra-competitive Los Angeles real estate market.
Despite her initial announcement in 2023 that she was stepping away from real estate to focus on her children and mental health, Wilkinson quickly clarified that she had not actually quit. “I just had a really bad day,” she admitted. “I should’ve never Instagrammed that I’m quitting, but I did on accident like an idiot, so I made a huge mistake.” She is now back in the business, working on multiple deals and embracing the daily challenges of the industry.
Life After the Mansion: Personal Growth and New Beginnings
Kendra Wilkinson’s journey since leaving the Playboy Mansion has been anything but easy. She has faced public scrutiny, a challenging divorce, and mental health struggles. Yet, through it all, she has remained open and honest about her experiences, using her platform to advocate for self-acceptance and mental health awareness.
Wilkinson’s candidness about her past and her willingness to share her struggles have resonated with fans. She has spoken about undergoing extensive therapy and working through anxiety and PTSD. “I’ve done extensive work on myself, through therapy and medication, to find peace with everything,” she explains. “I was overwhelmed with anxiety, but I’m done worrying.”
Her story is a reminder that personal growth is possible at any stage of life. Wilkinson’s ability to reinvent herself—from Playboy model to real estate agent to reality TV star—demonstrates resilience and adaptability. She is now focused on building a new future for herself and her children, proving that it’s never too late to chase your dreams.
The Impact of Reality TV and Public Scrutiny
One of the most challenging aspects of Kendra Wilkinson’s journey has been the intense public scrutiny that came with her reality TV fame. “Many individuals concentrate on the fact that I was in Playboy, but few consider what it truly took to film a reality television show and the toll it takes,” she says. “It demanded every bit of my spirit.”
Wilkinson has described the experience as “selling your soul to the devil,” acknowledging the immense cost that comes with fame. The constant attention from paparazzi and the pressure to maintain a public image took a significant toll on her mental health. “I struggled with a lot of PTSD, you know, just being the one who had years where paparazzi were just like, you know, just on me,” she recalls.
Despite these challenges, Wilkinson has found ways to reclaim her narrative and use her platform for good. She continues to speak out about the realities of fame and the importance of mental health, inspiring others to do the same.
Kendra Wilkinson’s Message to Fans: Embrace Change and Keep Moving Forward
Kendra Wilkinson’s story is ultimately one of hope and perseverance. She encourages her fans to embrace change, learn from their mistakes, and never be afraid to start over. “I want to publicly hate real estate again, but I can’t, because I love it,” she jokes. “I love real estate. It’s a challenge every single day.”
Her openness about her regrets, struggles, and triumphs makes her relatable to millions. Wilkinson’s journey reminds us that it’s okay to have regrets, as long as we use them as motivation to grow and pursue new opportunities.
Looking Ahead: What’s Next for Kendra Wilkinson?
As of June 2025, Kendra Wilkinson continues to work in real estate and remains a prominent figure in the entertainment industry. She is focused on her children, her career, and her own well-being. With each new chapter, she proves that it’s never too late to reinvent yourself and chase your dreams.
If you’re inspired by Kendra Wilkinson’s journey and want to learn more about her story, check out her latest interviews and follow her on social media for updates on her real estate ventures and personal growth.