The Late Hugh Hefner’s Former Girlfriends Now: Kendra Wilkinson, Crystal Harris 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

While all three women keep a low profile, 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.

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. While 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 (nee 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 with him until the day he died.

Since his passing, she has moved on with spaceship engineer Nathan Levi. The couple was first spotted together on a PDA-filled vacation in Mexico in July 2020, and they’re still going strong. Although she has a new flame, she will always love 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.

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“He changed my life, he saved my life,” she told People in 2017. “He made me feel loved every single day. He was a beacon to the world, a force unlike anything else.”

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

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