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  1. Feb 16, 2022 · The six-season series primarily highlighted his relationships with the likes of Holly Madison, Bridget Marquardt and Kendra Wilkinson. The final season of the show introduced...

  2. Sep 28, 2017 · Hefner had no shortage of girlfriends and wives during his tenure as one of the world's most notorious publishers. Here's a look back at some of Hefner's most memorable relationships. Barbi...

  3. Jan 29, 2022 · Tina Marie Jordan. 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 ...

  4. Jul 18, 2023 · Though the mansion had rules, the ladies pinpoint drama with Hefner’s other girlfriends as the reason for their exit. Here’s what we learned from Hefner’s former flames.

  5. Sep 26, 2022 · Hugh Hefner had many stunning girlfriends throughout his life. See photos of the models, including Kendra Wilkinson, Crystal Harris and more.

  6. 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.

  7. Jan 24, 2022 · Hefner's girlfriends spoke openly about double standards in their relationships with Hefner. They were not allowed to date despite his penchant for multiple girlfriends.

  8. Sep 28, 2017 · Hugh Hefner passed away Wednesday at 91-years-old and he sure did live a life fit for the founder of Playboy Enterprises. Here are some of the wives and girlfriends of Hefners past.

  9. Sep 28, 2017 · Hugh Hefner and Mildred Williams met in college at Northwestern University. The two married in 1949 and had two kids together: Christie, who was born in 1952, and David, born in 1955.

  10. en.m.wikipedia.org › wiki › Hugh_HefnerHugh Hefner - Wikipedia

    Hefner's former girlfriend Holly Madison said that he "would encourage competition—and body image issues—between his multiple live-in girlfriends. His legacy is full of evidence of the exploitation of women for professional gain."