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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.
- Mildred Williams
- Barbi Benton
- Sondra Theodore
- Carrie Leigh
- Kimberley Conrad
- Mandy and Sandy Bentley
- Brande Roderick
- Holly Madison
- Tina Marie Jordan
- Izabella St. James
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. The two divorced in 1959.
Benton met Hefner in 1968 when she was 18, and he was 42. The pair dated until 1976. She went on to marry Los Angeles entrepreneur George Gradow in 1979. Benton appeared on "Playboy After Dark," and after she split with Hefner went on to do modeling, singing and acting. HOLLY MADISON SAYS SHE WAS ‘AFRAID TO LEAVE’ PLAYBOY MANSION DUE TO ‘MOUNTAIN O...
Theodore met Hefner when she was 19 and he was 50 in the late '70s. Theodore was one of Hefner's exeswho spoke out in the docuseries. She recently spoke to Fox News Digital, where she alleged that Hefner manipulated her into participating in an orgy.
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. Leigh is an actress, most known for her roles in "A Fine Mess" and "The New Mike Hammer."
Conrad was Hefner's second wife. The two married in 1989 and remained married until 2009, despite separating in 1998. Conrad and Hefner had two sons together, Marston and Cooper. Cooper has recently spoken out, defending his late father amid the shocking A&E documentary.
Mandy and Sandy were the first set of twins that Hefner dated simultaneously around 2000. They lived in the Playboy mansion with Hefner and his other girlfriend at the time, Brande Roderick
Roderickdated Hefner for roughly a year from 2000-2001. Roderick was named Playmate of the Year in 2001. Roderick is a model and actress most known for her appearances in "Baywatch," "The Apprentice" and "Starsky & Hutch."
Madisonmoved into the Playboy mansion at the age of 21. She dated Hefner from 2001 until 2008. Madison starred in "Girls Next Door" alongside Bridget Marquardt and Kendra Wilkinson. She went on to have her own show, "Holly's World." In the A&E doc, Madison claimed she was afraid to leave the Playboy Mansionout of fear of repercussions, specifically...
Hefner dated Tina Marie Jordan for one year in 2000-2001. Following her time in the "Playboy" videos, Jordan made appearances on "Howard Stern," "Late Night Poker" and "The Girls Next Door." She also hosted the radio show "Two Chicks and a Bunny" from 2004 until 2006.
St. James dated Hefner from 2002 until 2004. She was in law school when she met Hefner. Since her time living in the mansion, St. James wrote the book "Bunny Tales: Behind Closed Doors at the Playboy Mansion" detailing her experience.
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- Lauryn Overhultz
- 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.
- Barbi Benton. 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.
- Shannon Tweed. 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.”
- Mildred Williams. 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.
- Kimberley Conrad. 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.
Holly Madison was Hefner’s girlfriend for seven years. She moved in to the mansion when she was 21-years-old and left at the age of 28. Tina Marie Jordan (2000-2001) Tina was Hefner’s...
Jul 18, 2023 · 1:20. For a time, Hugh Hefner had more than a few some bunnies to love. The Playboy founder, who died in 2017 at 91, famously once had seven girlfriends. The second episode of the sophomore...
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Apr 16, 2022 · Libby TorresApr 16, 2022, 18:17 IST. Hugh Hefner and Crystal Hefner in 2014.Charley Gallay/Getty Images for Playboy. Hugh Hefner was romantically linked to numerous women throughout his...
