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.

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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.



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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Bridget Marquardt

From 2002 to 2008, the Playboy model was one of Hugh’s original girlfriends on The Girls Next Door. These days, she has been busy vlogging on YouTube and hosting her podcast, Ghost Magnet, which investigates paranormal activity. She’s been dating film director Nick Carpenter since 2009 and they seem happier than ever.


Brande Roderick

The former Baywatch actress dated Hugh from 2000 to 2001. Brande got married in 2007 to former NFL player Glenn Cadrez and welcomed three kids together. They later got divorced in 2017. These days, she runs her fantasy gaming website, FantaZ.

The Shannon Twins

Kristina and Karissa Shannon weren’t the first twins to simultaneously date Hugh Hefner (and live in the mansion). Hugh previously called the Bentley twins his girlfriends from 1999 to 2000. The Shannon twins appeared on an episode of Botched in 2015, during which they detailed their unfortunate plastic surgery stories. Today they are still working as bombshell models.

Izabella St. James

The Polish Playmate penned the first tell-all written by one of Hef’s former lovers. She dated him from 2002 to 2004. According to her Instagram bio, she is the founder and CEO of The Pug Queen Foundation.

Tina Marie Jordan

Overlapping with Brande, Tina Marie was Hef’s girlfriend for just a year, from 2000 to 2001. She previously hosted a radio show but mainly stays out of the spotlight today.

Holly Madison

She was with Hef for seven years and used to be considered his “No. 1,” but since her Playboy Mansion days, Holly has gotten married and given birth to two children — Rainbow and Forest. The star has also penned two salacious memoirs about her days as Hef’s lover and has even made allegations of abuse against her former beau.

Kendra Wilkinson

Following Kendra’s time on The Girls Next Door, she went on to star in a few of her own reality shows. Since then, she married and got divorced from former NFL player Hank Baskett. Today the exes do their best to coparent their children.

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Crystal Harris

Following her days with Hef, Crystal has opened up about her struggles with Lyme disease and admitted to having her breast implants removed. In recent years, she keeps herself busy by traveling around the world with her boo, Nathan Levi. She recently claimed in 2021 that Holly and Bridget “despise her” and that she “sided with Kendra” during their feud.