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Mar 29, 2022 · Former Girls Next Door stars Karissa and Kristina Shannon have opened up about how they both contracted chlamydia while living with Hugh Hefner at the Playboy Mansion, with Karissa revealing...
- Carly Stern
- 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.
- 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.
- 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.
- 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.
Mar 22, 2022 · Karissa and Kristina Shannon, aka the Shannon twins, dated Hugh Hefner between 2008 and 2010. Born in October 1989 in Ann Arbor, Mich., the girls moved from a Florida trailer park to Los Angeles when they were 18.
- Leila Kozma
Dec 10, 2021 · Kendra Wilkinson was a 19-year-old aspiring model from San Diego on the night she met Hugh Hefner, later becoming Hef's girlfriend and moving into the fabled Playboy Mansion. In fact, Wilkinson was one of the Playboy mogul's three girlfriends housed at the famed estate.
- Brent Furdyk
- Hugh Hefner’s Romances: His Wives and Girlfriends Through the Years. Hugh Hefner, who died in September 2018 at age 91, was always surrounded by beautiful women.
- Mildred Williams. Before he launched the magazine in 1953, Hefner had already fallen in love with Mildred “Millie” Williams. The pair were together during his stint in the army from 1944 to 1946, and when he returned he found out Williams had an affair with another man.
- Marilyn Cole. British model Cole had a brief relationship with the businessman. She was 1973’s Playmate of the Year and eventually married Victor Lownes, who was once president of the Playboy Enterprises.
- Lillian Muller. Muller first met Hefner in the 1970s after a scout for his empire found her in London. She became Playmate of the Year in 1976 and appeared on the magazine’s cover eight times.
Jan 23, 2024 · October 2008. The twosome met when Crystal was 21 when she attended a Halloween party at the Playboy Mansion. That same month, she was named “Co-Ed of the Month” on Playboy.com. October 2009....
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Jan 24, 2024 · Crystal Harris was 21 when she met Playboy Magazine founder Hugh Hefner, who was 60 years her senior. They eventually married, and she lived in the Playboy Mansion until he died in 2017 at age...