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The Late Hugh Hefner’s Former Girlfriends Now: Kendra Wilkinson, Holly Madison and More

The most famous ladies man in history — Hugh Hefner — will always be remembered for having beautiful girlfriends throughout his life in the spotlight.

The founder and chief creative officer of Playboy Enterprises, who died in September 2017 at the age of 91, infamously dated blonde after blonde, even in his later years. He certainly had his fill of bombshells and previously admitted to sleeping with “more than” 1,000 women.

Fans of the media mogul fell in love with Hef’s many girlfriends just as he did, especially the cast of his hit reality show, The Girls Next Door. Today, his ex-girlfriends Kendra WilkinsonBridget Marquardt and Holly Madison, live very different lives from their days in lingerie at the playboy mansion.

holly madison, girls next door

Kendra is a proud mother of two children, Hank and Alijah, with ex-husband Hank Baskett, and she can’t help but gush over her adorable kids. In April 2020, she exclusively told In Touch she loves “spending so much time” with her children and is grateful for their days at home together during the coronavirus pandemic. “It’s actually been really incredible,” she shared at the time.

While the girls have fulfilling lives of their own now, they don’t necessarily have warm and fuzzy feelings about their days in the Playboy mansion — or each other.

Although Holly says she’s “always been close” with Bridget on the “Call Her Daddy” podcast in 2021, she simply answered “no” when asked if she still talks to Kendra.

She then went a step further and questioned whether Kendra had been honest in the past when she claimed she never slept with Hef before moving into the mansion. “I had to sleep with him first,” the Showgirl Next Door author said. “I’m not trying to slut shame anybody or anything, but nobody ever got asked to move in unless they had slept with him.” For her part, Kendra responded on Instagram, writing, “Times have changed. I forgive and have kids to love and focus on.”

As for Hef’s next trio of girlfriends — Crystal Hefner (née Harris) and twins Kristina and Karissa Shannon whom fans met in later seasons of his E! reality show, they are also living quieter lives today. Crystal went on to marry the millionaire in 2012 and was with him until the day he died.

Since his passing, she has moved on with spaceship engineer Nathan Levi and more recently, actor Ryan Malaty. Although she has a new flame, she will always have love for her late husband. In September 2019, Crystal shared a sweet tribute on the anniversary of his death. “Missing you for two years today,” she wrote on Instagram.

Ahead of the A&E documentary, Secrets of Playboy, the former spouse of Hef revealed she was being told to “tell her story” and share never-before-heard details about her time with him.

“I’m always torn when I talk about the Playboy Mansion because in a [lot] of ways, it was a sanctuary to me, but in other ways, it was my prison,” Crystal wrote on Instagram in January 2022. “The same with Hef. He was good to me in many ways, but in other ways, he wasn’t. I’m still healing from certain experiences.”

Scroll through the gallery to see what Hugh Hefner’s exes look like then and now!

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