Kendra Wilkinson: My Relationship With Hugh Hefner was ‘Heavenly’

May 14, 2025 - 21:00
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Kendra Wilkinson: My Relationship With Hugh Hefner was ‘Heavenly’
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Kendra Wilkinson had an overall positive experience at Playboy — mostly.

Very recently, Holly Madison spoke of how much she hated aspects of her erstwhile relationship with Hugh Hefner.

While the Girls Next Door alums did not get along at the time, they have also clashed over their divergent experiences with the now deceased businessman.

They still do not see eye to eye on many things. As far as Wilkinson is concerned, her relationship with the 60-years-older Hefner was “heavenly” and exactly what she needed at the time.

Kendra Wilkinson on the May 8, 2025 'Skinny Confidential' podcast episode.
In May of 2025, Kendra Wilkinson appeared on the ‘Skinny Confidential’ podcast. (Image Credit: YouTube)

Kendra Wilkinson says that ‘there couldn’t have been a better experience’ for her

In 2004, Kendra Wilkinson was 18. This is when she began her relationship with late Playboy founder Hugh Hefner.

That relationship would span 5 years. Hefner was also dating Holly Madison and Bridget Marquardt.

Despite Madison’s recent, strongly-worded expressions of disgust, Wilkinson has nothing negative to say about that time.

Kendra Wilkinson on the May 8, 2025 'Skinny Confidential' podcast episode.
On the podcast, Kendra Wilkinson discuses how she built a 20-year personal brand starting in her teens. (Image Credit: YouTube)

“It was like heaven, it was a heavenly experience for me,” Wilkinson gushed on a recent episode of the Skinny Confidential podcast. “Like there couldn’t have been a better experience.”

At least, that’s true as far as the relationship with the elderly businessman went.

“I have bad experiences when it comes to the business side of things,” Wilkinson did acknowledge. “Not Heff.”

‘I was not dating Hugh Hefner’

“Heff was a very awesome guy to me,” Kendra Wilkinson raved. “He was a generous, nice person. A very nice person. I don’t see him in any other way.”

Hugh Hefner, who is notorious for multiple reasons, was 78 years old at the time.

“He was a great friend to me, we loved each other in a different way,” Wilkinson said. She indicated that the relationship was not what some people imagine.

Kendra Wilkinson on the May 8, 2025 'Skinny Confidential' podcast episode.
By her own admission, Kendra Wilkinson arrived to a 2025 podcast interview while struggling with a hangover. (Image Credit: YouTube)

Despite the sexual relationship and the bond that she felt with the then-septuagenarian, she does not describe it as “dating” Hefner.

“I was not dating Hugh Hefner. I had like boyfriends — I had so many boyfriends,” Wilkinson described.

“That’s why I was ready for marriage at that time,” she continued. “Because I went through my real dating process while I was at the mansion. Never really got out, but I had my fun.”

Kendra Wilkinson for EW in 2023.
Speaking in a 2023 interview with Entertainment Tonight, Kendra Wilkinson talks about her career, her past, and life as a single mom. (Image Credit: Entertainment Tonight/YouTube)

‘I was in survival mode’

In 2009, Kendra Wilkinson departed the mansion. She went on to marry now ex-husband Hank Baskett. They share 14-year-old Hank Jr. and 10-year-old Alijah.

“I had to do what I had to do,” Wilkinson recalls of her time at the mansion and starring on Girls Next Door. “I had to survive.”

She continued: “I was in survival mode. I chose what I chose: I made the choice to move into the Playboy Mansion, have sex for money with Hugh Hefner.” She affirmed that she “actually lived an amazing five years of my life.”

Kendra Wilkinson: My Relationship With Hugh Hefner was ‘Heavenly’ was originally published on The Hollywood Gossip.

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