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Highlights

• Both Kendra Wilkinson and Holly Madison have had traumatic experiences living with Hugh Hefner, but they support their daughters' choices unconditionally.
• Kendra doesn't want to hold her daughter back from posing for Playboy in the future, wanting her to live her own life and learn from her experiences.
• Holly, on the other hand, wants to prevent her daughter from following in her footsteps, teaching her to be confident without exploiting herself and to have respect for herself.

In 2005, people started to watch the lives of Hugh Hefner's main girlfriends, Kendra Wilkinson, Holly Madison, and Bridget Marquardt in the Playboy Mansion on E!'s reality series, The Girls Next Door. It all seemed like a glamorous life until 2015 (five years after the show wrapped) when Madison released her bombshell memoir, Down the Rabbit Hole.

True to its subtitle, the book featured "Cautionary Tales of a Former Playboy Bunny," which caused tension between the author and Hefner, as well as Wilkinson – who denied Madison's claim that all of them had to sleep with Hef before moving in. But after the release of the docu-series, Secrets of Playboy in 2022, it seems like they've found a way to "move forward" by opening up about their past.

Both Madison and Wilkinson admitted to having "traumatic" experiences living with Hefner at a young age. You'd think that would make them strict with their daughters. But both of them have found a way to support their children, unconditionally, even if they decide to follow in their moms' footsteps someday...

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Kendra Wilkinson "Doesn't Want To Hold Back" Her Daughter From Posing For Playboy Someday

In 2014, Wilkinson and her then-husband, Hank Baskett were just expecting their second child, Alijah Mary, who's turning 10 this year. Their firstborn, Hank IV is now 14 years old. At that time, the model-turned-realtor said they were picking out "unisex" names for Alijah because they wanted her to be a tomboy. "We have picked our top five and they're all unisex names. We want her to be a tomboy, like me," Wilkinson explained.

When asked if she'd mind Alijah posing for Playboy someday, Wilkinson said: "I don't want to hold her back, because I was never held back. I want her to live her life doing what's right for her at the time. She needs to live and learn."

A decade later, the single mom says she's "trying to correct" some things in her parenting to give her daughter a nice future. "I look back at what happened to where I felt like I had to date an older man at 18. What drove me to that place, and why did I choose to do that?" Wilkinson told People in January 2024. "These are things I'm trying to correct in my parenting to my daughter. What can I do to show her [Alijah] that she's more than that?"

She added that "at the end of the day, [she doesn't want her] daughter sexualized at a young age like" she was. On finally speaking up about her time with Hefner, she said: "Hugh Hefner lived his life. That was his life. I'm not going to sit here and protect him while I'm focusing on raising two kids."

Kendra Wilkinson admitted to People that she had sex with Hugh Hefner (2024) after saying she didn't in 2014; and that she was simply invited to live in the Playboy Mansion.

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Holly Madison Wants Her Daughter To Know "All" Her Playboy "Ups And Downs"

In 2016, Madison and her then-husband, Pasquale were expecting their now-eight-year-old son, Forest. Their daughter, Rainbow had just turned three at that time. In an exclusive with People back then, the former TV star said that she "would love for [her] daughter to learn from [her].

She said she wants to "share all [her] experiences, the ups and downs" with Rainbow. But unlike Wilkinson, when the Girls Next Level podcaster was asked if she'd let her daughter pose for Playboy, she said, "Never."

"I want her to be confident and realize that there are ways to feel beautiful without exploiting yourself or putting yourself out there in a way you might regret," Madison said of preventing her daughter from following in her footsteps.

"I want her to have respect for herself," added the Vegas Diaries author. Madison is also teaching Rainbow to be "a lot more spoken" than she was during her Playboy years. "I want Rainbow to learn to be verbal and stand up for herself," she shared. "If I could go back, I'd be a lot more outspoken. I wouldn't have allowed myself to be made to feel less than."

Holly Madison has an impressive net worth of $16 million despite not inheriting anything from Hugh Hefner's estate .

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Kendra Wilkinson & Holly Madison "Respect" Each Other's "Traumatic" Experiences With Hugh Hefner

After a decade of feuding with Madison, Wilkinson told People that she "respects" the stories of Hef's other ex-partners. "I respect what they've been through — I respect their stories," she told the magazine. "I was just there to be young, crazy, stupid, and I did that. I lived in a really crazy place for five years and I've moved on. Can we not include Hef in my life moving forward?"

The Kendra Sells Hollywood star also confessed that healing meant "facing" her traumatic past at Playboy. "I had to open up those dark questions like, 'Why did I do this? 'What really happened to me?' 'Is this bad? Did something bad happen to me? Was it a bad thing to do to live at the Playboy mansion?'" she recalled.

"At the end of the day, I had to really face the truth of it all. I had to face myself," Wilkinson said of forgiving her 18-year-old self for moving in with Hefner who was 60 years her senior.

As for Madison, she developed a stutter due to her trauma from living in the "cult-like" Playboy Mansion. "The reason I think the mansion was very cult-like looking back on it is because we were all kind of gaslit and expected to think of Hef as like this really good guy," she said in Secrets of Playboy. "And you started to feel like, 'Oh, he's not what they say in the media, he's just a nice man'"

Madison "was in a state of shell-shock" when she left the Playboy Mansion in 2008. "I can't even tell you what I did on my first day out or what it was like," she told Fox News Digital. "I just knew I had to hit the ground running as far as establishing a life for myself and a career for myself. I needed to find a livelihood.

On whether Madison would do Playboy all over again, she said: "Absolutely not. I couldn't take the drama, I couldn't take the stress. There's no way."

"I'm more about being fulfilled through work and my interests, not trying to chase fame or looking a certain way," the mother of two said of her current life. "When I was younger, I saw Hef as this amazing, generous, intelligent person who could just do no wrong," she explained. "And obviously, I learned that wasn't the case… Now, I look at things from different perspectives. I look at things as nuance. People evolve… And things are multifaceted."

Kendra Wilkinson's net worth is $10 million less than Madison's. It was also reported that money issues caused her divorce from Hank Baskett.

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