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The Wall Street Publication > Blog > Entertainment > Kendra Wilkinson Raves Over ‘Heavenly’ Hugh Hefner Relationship
Entertainment

Kendra Wilkinson Raves Over ‘Heavenly’ Hugh Hefner Relationship

Editorial Board Published May 14, 2025
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Kendra Wilkinson Raves Over ‘Heavenly’ Hugh Hefner Relationship
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Studying Time: 3 minutes

Kendra Wilkinson had an general constructive expertise at Playboy — principally.

Very not too long ago, Holly Madison spoke of how a lot she hated features of her erstwhile relationship with Hugh Hefner.

Whereas the Women Subsequent Door alums didn’t get alongside on the time, they’ve additionally clashed over their divergent experiences with the now deceased businessman.

They nonetheless don’t see eye to eye on many issues. So far as Wilkinson is anxious, her relationship with the 60-years-older Hefner was “heavenly” and precisely what she wanted on the time.

In Might of 2025, Kendra Wilkinson appeared on the ‘Skinny Confidential’ podcast. (Picture Credit score: YouTube)

Kendra Wilkinson says that ‘there couldn’t have been a greater expertise’ for her

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

That relationship would span 5 years. Hefner was additionally courting Holly Madison and Bridget Marquardt.

Regardless of Madison’s current, strongly-worded expressions of disgust, Wilkinson has nothing unfavourable to say about that point.

Kendra Wilkinson on the May 8, 2025 'Skinny Confidential' podcast episode.On the podcast, Kendra Wilkinson discuses how she constructed a 20-year private model beginning in her teenagers. (Picture Credit score: YouTube)

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

A minimum of, that’s true so far as the connection with the aged 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’s infamous for a number of causes, was 78 years previous on the time.

“He was a great friend to me, we loved each other in a different way,” Wilkinson mentioned. She indicated that the connection was not what some folks think about.

Kendra Wilkinson on the May 8, 2025 'Skinny Confidential' podcast episode.By her personal admission, Kendra Wilkinson arrived to a 2025 podcast interview whereas battling a hangover. (Picture Credit score: YouTube)

Regardless of the sexual relationship and the bond that she felt with the then-septuagenarian, she doesn’t 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.Talking in a 2023 interview with Leisure Tonight, Kendra Wilkinson talks about her profession, her previous, and life as a single mother. (Picture Credit score: Leisure 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 recollects of her time on the mansion and starring on Women Subsequent 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.”

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