Kendra Wilkinson Reflects on Past Regrets from Playboy Mansion Days

Kendra Wilkinson shared her thoughts on missed opportunities during her time at the Playboy Mansion in a recent interview. The 39-year-old, who has transitioned into a real estate agent, reflected on her years as one of Hugh Hefner’s girlfriends from 2004 to 2009.

“One thing I can say is that I didn’t start my real estate career while living in the Playboy Mansion,” she confessed on the red carpet at the 25th Los Angeles Smile Fiesta for Operation Smile. “What was I thinking? I mean, I was around so many celebrities and billionaires. But now I’m in real estate, so I’m doing fine.”

Wilkinson embarked on her real estate journey after successfully passing the California real estate exam in June 2020. A month later, she joined the luxury real estate firm, The Agency, founded by Mauricio Umansky, who is married to Kyle Richards from “The Real Housewives of Beverly Hills.”

She later moved on from The Agency to Douglas Elliman, a high-end real estate firm. In November 2021, she premiered her reality show, “Kendra Selling Hollywood,” which chronicled her adventures and challenges in the competitive luxury real estate scene in Los Angeles. The show lasted for two seasons on Discovery+ and Max.

In May 2023, Wilkinson hinted on Instagram that she was stepping back from real estate, but later clarified in a September interview that she hadn’t truly quit. “I just had a bad day,” she explained. “I made a dramatic announcement that I was leaving, and I probably shouldn’t have. It was a mistake.” She assured fans she was back in the game, mentioning that she had multiple deals in the works.

Working in real estate, she remarked, is “very stressful,” yet she expressed a desire to dive in again. “I want to publicly hate real estate, but I love it, so I can’t. It’s a daily challenge.” Initially, when she spoke about leaving, she cited the need to focus on her children and mental health.

Wilkinson has two children, Hank IV and Aliya, with her ex-husband Hank Baskett. She has been candid about her mental health struggles, including a panic attack that led to her hospitalization in September 2023. A representative indicated she was discharged the same day, but she had to return a week later. Doctors prescribed medication, and she began attending treatment several times a week.

“I was in a state of panic, not understanding what was happening to me,” she shared. “I felt weak and lost in a dark place.” She also opened up about the challenge of navigating her past as one of Hefner’s girlfriends, stating that “looking back at my 20s isn’t easy. I faced my own demons.”

She reflected on how her time at Playboy impacted her life. “It really ruined my life,” she stated, recalling the feelings of hopelessness and depression during that period. “I thought I’d never see the light.” Her real estate career was fraught with self-doubt, prompting questions about her successes and her life choices.

In the interview, she acknowledged the support of her medical team during her hospitalization, saying, “Without them, I wouldn’t be here now.” She emphasized the importance of having a strong support system, including friends, during difficult times. “It was a journey, but I’m feeling good now, really good,” she added with a smile.

Wilkinson was attending the Operation Smile event in Los Angeles, which aims to provide free surgeries and healthcare for children worldwide. “Operation Smile is an incredible cause,” she commented, underscoring the significance of the event and her dedication to supporting such important work.