Kendra Wilkinson Reflects on Her Journey with Sexuality and Relationships After Playboy Mansion Experience
Kendra Wilkinson is candidly sharing her ongoing journey regarding her relationship with intimacy and sexuality.
During a recent episode of the Amy Robach and T.J. Holmes’ I Do, Part 2 podcast, The Girls Next Door star shared how her time at the Playboy Mansion has shaped her views on relationships and intimacy. She revealed that even years later, she finds herself grappling with the challenges of establishing healthy connections.
At 39 years old, Wilkinson resided at the Playboy Mansion from 2004 to 2009, where she was one of Hugh Hefner’s prominent girlfriends alongside Holly Madison and Bridget Marquardt. This experience, showcased in the reality series The Girls Next Door, played a significant role in her understanding of romantic relationships.

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When Holmes probed how her experiences at the Playboy Mansion shaped her perceptions of love and relationships, Wilkinson honestly admitted, “Look, I still struggle to this day with my relationships and my views on sex.”
“I had to undergo a lot of therapy, and when they assessed me, they said — and this is the first time I’m admitting this — they mentioned, ‘You might have a little bit of a sexual issue. You may have a problem when it comes to thinking about sex,’” she continued, shedding light on her ongoing struggles.
As Robach pressed for clarification on what she meant by a “sexual issue,” Wilkinson elaborated, “You know, it’s just unhealthy thoughts. Not really settling for a marriage and things like that — which isn’t necessarily bad — I’m just saying that everyone has their choices, and some people want to be single, some people want to be married … and I’m more of a fun idea kind of person.”
Wilkinson, who was only 18 when she moved into the Playboy Mansion, eventually left at 23 after meeting Hank Baskett. The couple married and welcomed their son, Hank, now 15, and daughter, Alijah, now 10, before their split and divorce in 2018.

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Reflecting on her past, Wilkinson described her marriage as “the happiest days of my entire life,” and recounted the emotional turmoil that followed her separation from Baskett.
“Those days were the happiest days of my life. And when those days came to an end, I crumbled so hard, and it almost killed me,” she confessed. “It nearly killed me.”
“I left the Playboy Mansion at age 23, got pregnant, married at 23, and began my life as a wife and mother. Those were the golden years of my life,” she added, reminiscing fondly about that transformative period.
The devoted mother reflected on her decision to leave her glamorous life at the Playboy Mansion behind.
“It was the right timing. I found myself so bored at the Playboy Mansion. I was just like, ‘I am ready to leave this place. I am ready to start a family,” Wilkinson recalled. “I was ready for the … lifestyle: my kids attending a great school. I’m a soccer mom, a softball mom, a basketball mom. I was ready for that. I manifested it, and it came to me, and I met the right guy, the man of my dreams.”
“Even though we’re divorced, he is the father of my children, and he is the most amazing dad to my kids. I know I chose right with him,” she said of Baskett, highlighting the positive aspects of their co-parenting relationship.

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Holmes responded to Wilkinson’s praise of her ex-husband, questioning why they are not still together if her memories of their marriage are so positive. In response, Wilkinson acknowledged that they made “too many” mistakes, sharing that they were both quite “young.” She added that their mistakes rendered their marriage “not repairable at a certain point.”
Nevertheless, she admitted that she will “always be in love” with her ex-husband.
“It takes two people to be in a relationship … and when one person changes their mind about love and marriage, that’s how easy it is for it to disintegrate. So, I will always, always want my family back together,” Wilkinson expressed. “I will always want that. Until the day I die. I don’t know if I have another chance at marriage with that man or not. I will always want my kids to have those two parents together. But, unfortunately, that’s a fantasy.”
“It sounds like you’re still in love with Hank,” Robach noted, to which Wilkinson replied, “I will always be in love with Hank.”

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“Mistakes are mistakes,” she continued. “We all make mistakes. I’ve made my mistakes … but love will never go away. And if it’s real love, you’re going to put your pride aside and wish the best for the other person. And I want the best for the other person so badly. … There’s no need for bitterness, and there’s no need for toxicity.”
“Throughout these last six years, I’ve undergone a lot of therapy,” she added. “I’ve gone to the hospital for seven days to just reprogram my thinking, and I did that, and it really worked. So I’m now living in a state of peace of mind. You know, I’m on good meds. I’m just in a really good place.”
Wilkinson then provided an update on her current romantic life.
“I have nothing. I might dabble in some sex from time to time — but dating and being in a relationship? That’s the longest far-fetched thing I could possibly feel at the moment,” Wilkinson explained. “I’m in a bachelorette-type of vibe right now.”
However, she did mention that there are some prospects. “I do have two very young, attractive, ex-NFL players that are, like, all up on me right now, and it makes me feel young,” Wilkinson shared, hinting at the attention she’s receiving.