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Sep 28, 2017 · Learn about the women who dated or married the late Playboy founder, from Barbi Benton to Crystal Harris. See photos and read about their relationships, from scandals to marriages, in this comprehensive list.
- 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.
- 3 min
- Lauryn Overhultz
- Mildred Williams. Williams was the first wife of Hugh Hefner. The two met in college and got married in 1949. During their marriage, Hefner and Williams raised two children, Christie and David.
- Barbi Benton. Hugh Hefner met Barbi Benton in 1968, and the two dated until 1979. (Getty) Benton met Hefner in 1968 when she was 18, and he was 42. The pair dated until 1976.
- Sondra Theodore. Sondra Theodore and Hugh Hefner (Ron Galella/Ron Galella Collection via Getty Images) Theodore met Hefner when she was 19 and he was 50 in the late '70s.
- Carrie Leigh. Leigh dated Hefner and lived in the Playboy mansion for five years in the 1980s. She has been candid about her experience since leaving the mansion, describing it as an alleged "cult" during an interview with the Washington Post in 1999.
Sep 28, 2017 · A photo gallery of the women who shared the life of the late Playboy founder, from his first wife Mildred Williams to his last girlfriend Crystal Harris. See how their relationships evolved, from college sweethearts to reality TV stars.
- Rasha Ali
- 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.
Apr 22, 2021 · Learn about the Playboy founder's relationships with his three wives and several live-in girlfriends, from Barbi Benton to Crystal Harris. See photos and details of his marriages, affairs and reality TV show.
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Sep 28, 2017 · See the women who shared the life of the Playboy founder, from his college sweetheart to his last fiancée. Learn about their relationships, marriages, affairs and stories from his memoir and interviews.
