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- 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.
- Barbi Benton
- Shannon Tweed
- Mildred Williams
- Kimberley Conrad
- Holly Madison
- Kendra Wilkinson
- Bridget Marquardt
- Crystal Harris
Barbi Benton, nee Barbara Klein, met Hefner when she was an 18-year-old extra on “Playboy After Dark.” Hefner was 42 at the time and encouraged her to change her name. She went on to appear on four Playboy covers and posed nude in the magazine. “I was shy and would make the photographer turn his back when I changed poses,” Benton said of her photos...
Actress Shannon Tweed dated Hefner in 1982, the same year she was Playmate of the Year. Twenty-five years old at the time, Tweed starred on CBS soap opera “Falcon Crest.” Hefner was 56 at the time they dated. “When Shannon says, ‘Why don’t we get married?’ and I say no, she punches me,” Hefner said at the time, according to People magazine. “I thin...
Williams was Hefner’s first wife: the pair married in 1949 and divorced in 1959. The couple met at a party after high school, though Hefner left soon after for the United States Army. Williams cheated on himwhile he was overseas, but they still married. Hefner and Williams had two children together: Christie, 64, and David, 62.
Kimberley Conrad was Hefner’s second wife: they married in 1989 and divorced in 2010. The pair had two children together: Marston Hefner, 27, and Cooper Hefner, 26. The model and actress was named Playmate of the Month in January 1988 and Playmate of the Year in 1999.
Hefner and Madisonmet in 2001 during her tenure as a Playboy model. The two spent the night together and she moved into the Playboy Mansion soon after to become one of his many girlfriends. Madison and Hefner ended their relationship officially in 2008. She later published an expose on life in the Play Mansion called “Down the Rabbit Hole: Curious ...
Wilkinson met Hefner in 2004 at his 78th birthday party after she was hired to be a “painted girl” at the party, or a woman who appeared nude with painted on accessories. Wilkinson soon after moved into the Playboy Mansion and went on to star on the reality show “The Girls Next Door.” “Hef changed my life,” Wilkinson told E! News Wednesday. “He mad...
Marquardt, now 44, starred on “The Girls Next Door” alongside Madison and Wilkinson after moving into the Playboy Mansion in 2002. One of Hefner’s many girlfriends at the time, Marquardt appeared on the cover of Playboy in November 2005, September 2006 and March 2008. “So sad but forever grateful for all the wonderful memories and amazing experienc...
Harris was married to Hefner at the time of his death Wednesday. The couple met in 2008 and started dating in 2009. Named Playmate of the Month in December 2009 and donned the cover in July 2011 as “Mrs. Crystal Hefner.” Harris, 31, was more than 60 years younger than Hefner. “I think the center of her life is us and you can’t ask for more than tha...
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- 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.
- 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 · Where are Hugh Hefner's girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson now? Holly Madison left the mansion in 2008 after she and Hefner broke up. It was later revealed the couple split because he refused to get married.
- Christine Estera
Sep 28, 2017 · Brande Roderick (2000-2001) Roderick, a “Baywatch” actress, dated Hefner for one year. Holly Madison (2001-2008) Holly Madison was Hefner’s girlfriend for seven years. She moved in to...
Sep 28, 2017 · Playboy icon Hugh Hefner was notorious for his wives and girlfriends throughout his life -- from Barbi Benton to Kimberley Conrad, here's a complete list.
