Former Playboy model Kendra Wilkinson has one regret from her time at Hugh Hefner's mansion
Kendra Wilkinson revealed her biggest regret from her time at the Playboy Mansion.
During an interview with Fox News Digital, the 39-year-old TV personality-turned-real estate agent reflected on opportunities that she missed while living at the iconic Hollywood property as one of Playboy founder Hugh Hefner's girlfriends from 2004 to 2009.
'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,' the 'Girls Next Door' alum admitted while on the red carpet at the Operation Smile 25th Los Angeles Smile Fiesta.
'What was I thinking?' she added. '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.'
Wilkinson launched her career in real estate after passing the California real estate exam in June 2020.
A month later, Wilkinson was hired as a real estate agent at The Agency, the luxury real estate company founded by Mauricio Umansky, who is married to 'The Real Housewives of Beverly Hills' star Kyle Richards.
6 Kendra Wilkinson attends the 25th Annual Los Angeles Operation Smile Fiesta at Candela La Brea in Los Angeles, California on June 3, 2025.
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6 Wilkinson launched her career in real estate after passing the California real estate exam in June 2020.
Kendra Wilkinson/Instagram
Wilkinson later left The Agency to join the high-end real estate firm Douglas Elliman. In November 2021, Wilkinson debuted her reality series, 'Kendra Sells Hollywood,' which followed the former model as she navigated the ups and downs of her new career in Los Angeles' ultracompetitive luxury real estate market. 'Kendra Sells Hollywood' ran for two seasons on Discovery+ and Max.
In May 2023, Wilkinson announced on Instagram that she was stepping away from her real estate career. However, in a September interview with People, Wilkinson revealed that she hadn't actually given up her real estate career and admitted that she had been too hasty in announcing her departure from the business.
'I just had a really bad day,' Wilkinson said. '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,' she added. 'I have so many deals I'm working on right now.'
6 Hugh Hefner poses with Holly Madison, Bridget Marquardt and Kendra Wilkinson at the Fox Reality Channel Really Awards on Sept. 24, 2008.
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Wilkinson told People that though working in real estate is 'so stressful,' she 'wants to do it again.'
'I want to publicly hate real estate again, but I can't, because I love it,' Wilkinson said. 'I love real estate. It's a challenge every single day.'
When Wilkinson initially announced that she was quitting real estate, she explained that she made the decision so that she could focus on her children and her mental health.
Wilkinson shares son Hank IV and daughter Alijah, 11, with her ex-husband Hank Baskett.
Wilkinson has been candid about her struggles with her mental health after being hospitalized in September 2023 when she suffered from a panic attack.
6 Kendra Wilkinson and Hugh Hefner attend the Toyota Celebrity/Pro Race at Streets of Long Beach on April 14, 2007.
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At the time, a representative for Wilkinson said that she had been taken to the emergency room but would be released the same day.
In a January 2024 interview with People, Wilkinson shared that after she was released from the emergency room, she had to return to the hospital a week later.
Wilkinson explained that during her second visit, doctors prescribed her an antipsychotic medication, Abilify, and she attended therapy three times a week after her hospitalization.
'I was in a state of panic. I didn't know what was going on in my head and my body or why I was crying. I had hit rock bottom,' Wilkinson recalled of her medical crisis.
'I was dying of depression,' she continued. 'I was hitting the end of my life, and I went into psychosis. I felt like I wasn't strong enough to live anymore.'
She shared that professionals helped her handle unresolved trauma, which stemmed from living in the Playboy Mansion and her 2019 divorce from Baskett.
Wilkinson rose to fame at the age of 18 when she became one of Hefner's girlfriends and starred on the hit reality series 'Girls Next Door.'
'It's not easy to look back at my 20s. I've had to face my demons,' she admitted.
'Playboy really messed my whole life up,' the former model said.
'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,' she recalled. 'I was giving up and I couldn't find the light. I had no hope.'
The California native said before she was hospitalized, she was also struggling with her job in real estate, which caused her not to eat or sleep regularly.
''How am I going to succeed?' 'What am I doing wrong in my life?' 'Do I give up?'' Wilkinson said.
During her interview with Fox News Digital, Wilkinson recalled her hospitalization and praised her team of medical professionals for helping her through her darkest time.
'My health and happiness is such a blessing,' she said. 'I credit amazing doctors. I credit an amazing psychiatrist, psychologists, therapists, trainers, physical therapists. I mean, it keeps going on.'
'I mean without them, I wouldn't be standing right now,' she continued. 'I went through a lot with my mental health. I ended up hospitalized for about seven days.'
6 Wilkinson rose to fame at the age of 18 when she became one of Hefner's girlfriends and starred on the hit reality series 'Girls Next Door.'
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Wilkinson shared that she was hospitalized at the Ronald Reagan UCLA Medical Center, where she said that the team of doctors and nurses who treated her were 'so amazing.'
'They got me on the right meds, and I feel like a million bucks tonight,' she said. '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. 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 things.'
Wilkinson told Fox News Digital that having 'amazing friends that support me' was also crucial at that time.
'So yeah, it's been a journey, but I'm there,' she said. 'I feel good, and I'm smiling, and I never want to take my smile for granted.'
6 Kendra Wilkinson and Hugh Hefner attend Hugh Hefner's 83rd birthday dinner at Nine Steakhouse at the Palms Resort & Casino in Las Vegas on April 4, 2009.
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Wilkinson spoke with Fox News Digital while she was attending Operation Smile's 25th Los Angeles Smile Fiesta honoring Harrison Ford, Gene Simmons, and The Rodosky Family.
The event, which took place on June 3 at Candela La Brea in Los Angeles, benefited Operation Smile, a nonprofit organization that provides free cleft lip, palate surgeries and comprehensive healthcare to children worldwide.
Per a press release, Operation Smile 'works hand in hand with local volunteers, ministries of health, governments, universities, and communities to expand access to surgical care through training and education —starting with free, life-changing cleft surgery and comprehensive care.'
At the event, Ford received the Dr. Randy Sherman Visionary Award, named in honor of the late humanitarian and acclaimed plastic surgeon Dr. Randy Sherman, who was a longtime volunteer with Operation Smile and Ford's close friend. During his acceptance speech, Ford praised Sherman, saying 'there was no end to the grace, humility and love that this man embodied.'
While speaking with Fox News Digital, Wilkinson explained why supporting Operation Smile was important to her.
'Operation Smile is an amazing cause,' she said. 'It really transforms lives, it transforms lives all around the world, and it's just really such a great organization to support tonight. I'm here, I took my time out of my kids and my home to be here and stand with everyone here to really support this amazing cause.'
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