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She said that despite that time, she only hooked up with Hef once for about 15 minutes.

  • Like Madison and Wilkinson, Marquardt was never officially a Playmate herself, at least before she became one of his girlfriends for five years from 2003 to 2008.

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Holly Madison Holly Madison was perhaps the most well known girlfriend from the E! Barbi Benton Barbi Benton began her Playboy career at the age of 18 as the co-host of the entertainment show Playboy After Dark alongside Hef himself.

  • One of those sons now runs the magazine and was responsible for temporarily removing nudity.




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