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Kendra Wilkinson Opens Up About Struggles After Meeting Hugh Hefner at 18, Critiques ‘Playboy’ Influence on Her Life

Isla Emmet Isla Emmet | January 20, 2024 | 4 min read

Kendra Wilkinson has shared her experiences as Hugh Hefner’s girlfriend and how living at the Playboy Mansion impacted her.

At the age of 18 in 2004, Kendra met Hugh Hefner at his 78th birthday party while she was working as a painted lady. Intrigued by her, Hefner invited her to become one of his girlfriends.

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Kendra lived at the Playboy Mansion until 2009 when she encountered her future husband, Hank Baskett. While participating in the reality show “Girls Next Door,” Kendra was one of Hefner’s three girlfriends, alongside Holly Madison and Bridget Marquardt. Kendra and Hank Baskett’s relationship blossomed quickly, leading to their engagement and eventual marriage in 2009. Their love story drew parallels to other famous couples with significant age differences, which prompted discussions across media platforms; notably, Shakira speaks on age gap, sharing her insights on navigating relationships with age disparities. This made Kendra’s journey not just a personal narrative, but part of a broader conversation about love and connection across generations.

Kendra Wilkinson has opened up about her mental health struggles after her time at the Playboy Mansion, revealing doubts about the decisions she made in her youth.

Following a severe panic attack in September that led to her hospitalization, Kendra spoke to People about hitting rock bottom last year. She confessed, “I was dying of depression. I was hitting the end of my life, and I went into psychosis. I felt like I wasn’t strong enough to live anymore.”

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She attributes many of her struggles to her experiences at the mansion, stating, “It’s not easy to look back at my 20s. I’ve had to face my demons. Playboy really messed my whole life up.”

Since her hospitalization, Kendra has been on prescribed medication and is undergoing outpatient therapy three times a week to address trauma from her time at the mansion and her divorce from Hank in 2019.

Admitting to reaching the “lowest place [she’d] ever been in [her] life,” Kendra couldn’t envision a way forward in the depths of her depression. She pleaded with Hank, with whom she shares her 14-year-old son Hank IV and 9-year-old daughter Alijah Mary, to take her to the hospital.

Having faced numerous challenges, Kendra now feels a sense of protectiveness toward her younger self. She acknowledges experimenting with drugs at the age of 15 and describes herself as having “a lot of issues” during her teen years.

Entering the Playboy mansion at the age of 18, three years before reaching the legal drinking age, Kendra embraced the party lifestyle. However, she now openly acknowledges regret for the choices she made during her time there.

“I really got into deep regret [afterward]… deep. I struggled with depression before and at the mansion. I drank a lot. I was there for the partying, OK, let’s just be real. I was not there for Hugh Hefner to be my boyfriend,” she told PEOPLE.

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Kendra reflects on the impact of being objectified from a young age and living at the mansion, revealing that it took a toll on her self-esteem. She expressed, “I hated my chest, my body, my face. I got to that point where I started hating myself.”

Questioning her past decisions, she wonders, “Why did I be intimate with Hugh Hefner at that age? Why did I do that? Why did I go to the mansion in the first place? Why did I get big chest? Why am I a intimacy symbol? Why did I bleach blonde my hair? Why did I do this to myself? Why did I?”

Now, Kendra is actively working to break free from the “vortex of horrible things” in her past and focus on her burgeoning real estate career.

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Kendra is determined to steer her own daughter away from a similar path, expressing her desire, “I see loopholes in my life where I’m trying to correct now so my daughter doesn’t have to experience what I did at a young age. I don’t want my daughter objectified like I was.”

Reflecting on her past choices, especially dating an older man at 18, she questions, “What brought me to that point? These are the things I’m trying to correct in my parenting for my daughter. What can I do to show her that she is more than that?” Kendra emphasized that her focus, now in real estate, is a genuine gift she wants to provide for her children.

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Source: PEOPLE


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Isla Emmet
Written by
Isla Emmet

Isla is a relationship writer and former counsellor based in London. With a background in psychotherapy and five years of writing about love, attachment, and emotional wellbeing, she brings a calm and deeply empathetic voice to every piece. Isla believes that understanding yourself is the first step to understanding the people you love. When she is not writing, she is hiking the Scottish Highlands or curled up with a good novel and a strong cup of tea.