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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. Apr 22, 2021 · Who were Hugh Hefner's girlfriends? Hugh Hefner reportedly slept with more than 1,000 women in his lifetime. The magazine founder famously owned the sprawling Playboy Mansion in Holmby Hills, just off Sunset Boulevard in LA — and it was a revolving door of celebrities and playmates.

  5. 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.

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

  7. 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.

  8. 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.

  9. 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.

  10. 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.