Kendra Wilkinson, a name synonymous with the glitz and glamour of the Playboy Mansion, recently made headlines by sharing a singular regret from her time as one of Hugh Hefner’s girlfriends. At 39, the former reality TV star turned real estate agent opened up about her five-year stint at the iconic Los Angeles estate, revealing a missed opportunity that still lingers in her mind. Speaking at the Operation Smile 25th Los Angeles Smile Fiesta, Wilkinson reflected on her journey from the mansion’s wild parties to her current life as a successful realtor and mother of two. Her candid admission offers a fresh perspective on a chapter of her life that captivated millions through the reality show The Girls Next Door. Let’s dive into Kendra’s story, exploring her regret, her transformation, and the lessons she’s learned along the way.
Table of Contents
From Playboy Bunny to Real Estate Star
Kendra Wilkinson’s journey began in 2004 when, at just 18, she caught the eye of Playboy founder Hugh Hefner at his 78th birthday party. She soon moved into the Playboy Mansion, joining Hefner’s trio of live-in girlfriends alongside Holly Madison and Bridget Marquardt. The trio starred in The Girls Next Door, a reality show that offered a glimpse into their lavish, often controversial lifestyle. While the mansion was a whirlwind of parties, fame, and media attention, Wilkinson now sees a missed opportunity that could have shaped her career differently.
Her regret? Not kickstarting her real estate career while living at the mansion. During her recent interview, she shared that she wishes she had pursued real estate sooner, a path she now thrives in. “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 told reporters. This reflection highlights her shift from a young woman navigating fame to a driven professional carving her own path in Los Angeles’ competitive real estate market.
Kendra Wilkinson’s Regret: A Missed Opportunity
What makes Kendra Wilkinson’s regret so compelling is its focus on professional growth rather than personal choices. Living at the Playboy Mansion offered her fame, but it also came with limitations. At 18, she was thrust into a world of photo shoots, TV appearances, and high-profile events, leaving little room for long-term career planning. Wilkinson now recognizes that the mansion’s resources and connections could have been a springboard for her real estate ambitions.
She explained that she missed out on “major career opportunities” during her time there. The mansion, while a hub of glamour, wasn’t conducive to building the skills she needed for a sustainable future. Instead, she leaned into the reality TV spotlight, which brought her fame but also challenges, including public scrutiny and personal struggles. Her regret underscores a universal truth: youth often prioritizes the present over the future, a lesson Wilkinson learned the hard way.
The Playboy Mansion: A Double-Edged Sword
Life at the Playboy Mansion was a mix of extravagance and complexity. For Kendra Wilkinson, it was both “heavenly” and “lame,” as she described in a podcast appearance. She moved in at 18, navigating a relationship with Hefner, who was 60 years her senior, alongside Madison and Marquardt. The mansion offered a safe haven compared to her turbulent teenage years, but it also came with intense pressure to maintain a certain image. Wilkinson has spoken openly about feeling sexualized, a reality that shaped her views on intimacy and relationships long after she left in 2009.
Despite these challenges, she harbors no ill will toward Hefner or the mansion. “I had to do what I had to do,” she said, emphasizing that her choices were her own. Her ability to reflect on this time without bitterness sets her apart from other former Playmates, some of whom have shared more negative experiences. Wilkinson’s regret isn’t about her time with Hefner but about not leveraging that chapter for professional growth.
Transitioning to a New Chapter
By 2009, Kendra Wilkinson was ready to leave the mansion behind. At 23, she married NFL player Hank Baskett, starting a family with their two children, Hank IV and Alijah. Her reality TV career continued with shows like Kendra and Kendra on Top, which documented her life as a wife and mother. However, her marriage ended in 2018, marking a turning point. Wilkinson faced personal and financial challenges, moving from a $2.5 million home in Calabasas to a $3,500-a-month rental in Agoura Hills. These struggles pushed her to reinvent herself.
Her pivot to real estate was a game-changer. Today, she’s a successful realtor in Los Angeles, recently hosting an open house for a $1.5 million property in Westlake Village. Gone are the days of racy outfits and stilettos; Wilkinson now commands respect in professional attire, armed with a clipboard and a passion for her work. Her regret about not starting this career earlier fuels her drive to succeed now.
Kendra Wilkinson’s Regret in Context
Kendra Wilkinson’s regret isn’t just about missed opportunities; it’s a reflection of her growth. She acknowledges that the mansion’s environment, while glamorous, limited her ability to focus on long-term goals. The constant demands of filming, public appearances, and maintaining the Playboy image left little time for self-development. “I was so caught up in the lifestyle,” she admitted, noting that she didn’t prioritize education or career planning.
This regret resonates with many who look back on their younger years and wish they’d made different choices. For Wilkinson, it’s not about dwelling on the past but learning from it. She’s now focused on building a legacy for her children, encouraging her daughter Alijah to pursue college and explore her options—choices Wilkinson didn’t feel she had at 18.
The Impact of the Playboy Experience
Wilkinson’s time at the mansion wasn’t without its downsides. She’s been open about the lasting impact on her mental health and views on sex. In a March 2025 podcast, she revealed that her relationship with Hefner left her with “unhealthy thoughts” about intimacy, a struggle she’s addressing through therapy. “I still struggle with my relationships and my views on sex,” she shared, highlighting the long-term effects of being sexualized as a teen.
Despite these challenges, she views her mansion years as formative. “It was the golden years of my life,” she said, reflecting on her transition from the mansion to motherhood. Her ability to balance these mixed feelings—acknowledging both the positives and negatives—shows her resilience. Wilkinson’s regret about her career path doesn’t overshadow her gratitude for the experiences that shaped her.
Relationships at the Mansion
Kendra Wilkinson’s time at the mansion wasn’t just about Hefner; it also involved navigating relationships with Madison and Marquardt. She’s been candid about feeling like an outsider, describing herself as the “third wheel” in the trio. “I never bonded with Holly Madison,” she admitted, citing personality clashes and the competitive dynamics of the mansion. While she had a good friendship with Hefner, her relationships with her co-stars were strained.
These tensions carried over into later years. Madison’s 2015 memoir described Wilkinson as “the fakest person” she’d ever met, sparking a public feud. Wilkinson fired back on social media, defending her experience and choices. Recently, Madison expressed openness to reconciling, but Wilkinson has remained focused on her own path, suggesting she’s moved beyond the drama.
A Mother’s Perspective
As a mother, Kendra Wilkinson is intentional about how she discusses her past with her children. She’s already talking to her 10-year-old daughter, Alijah, about college and future opportunities. “I wouldn’t want her to be in that position of having to choose that,” she said of her mansion days. While she doesn’t regret her choices, she wants her daughter to have more options than she did at 18.
Wilkinson’s transparency with her kids is refreshing. She doesn’t shy away from her past, including her decision to “have sex for money” with Hefner. Instead, she frames it as a choice she made in a specific context, emphasizing personal agency. This approach reflects her growth and her desire to guide her children toward informed decisions.
Kendra Wilkinson’s Current Success
Today, Kendra Wilkinson is thriving in her real estate career. Her recent appearance at a $1.5 million open house in Westlake Village showcases her hustle. Fans have taken to social media to celebrate her transformation, with one X post praising her journey from the mansion to raising two kids and succeeding as a realtor. “She’s come so far,” the post read, echoing the sentiment of many who admire her resilience.
Her regret about not starting real estate sooner hasn’t held her back. Instead, it’s motivated her to seize opportunities now. Wilkinson’s story is one of reinvention, proving that it’s never too late to pivot and pursue your passion. Her work ethic and authenticity resonate with fans, making her a relatable figure in a world often obsessed with perfection.
Lessons from Kendra’s Journey
Kendra Wilkinson’s regret offers valuable lessons for anyone reflecting on their past. First, it highlights the importance of planning for the future, even in the midst of exciting opportunities. Second, it shows that regret can be a catalyst for growth rather than a source of shame. Wilkinson’s ability to channel her regret into a thriving career is inspiring.
Her story also underscores the power of resilience. From navigating the complexities of the Playboy Mansion to overcoming personal and financial challenges, Wilkinson has emerged stronger. She’s not defined by her past but by how she’s used it to build a brighter future.
Looking Ahead
As Kendra Wilkinson continues her real estate journey, her focus remains on her career and her children. She’s open about her struggles, from mental health challenges to the lingering effects of her mansion days, but she’s equally vocal about her happiness. “I feel good and mentally healthy,” she shared on Instagram, a testament to her growth.
Her regret about not starting her real estate career earlier is a small part of a larger story of triumph. Wilkinson’s ability to reflect, learn, and move forward makes her a compelling figure. Whether she’s hosting an open house or sharing life lessons with her kids, she’s proving that the past doesn’t define you—it’s what you do next that matters.
Follow Kendra Wilkinson’s journey and share your thoughts on her transformation in the comments below. How do you think her experiences shape her advice for the next generation?