Hugh Hefner and Barbi Benton - April 7, 1973

  Carrie Leigh and Hugh Hefner - "Beverly Hills Cop II" (1987) Los Angeles Premiere on May 19, 1987

  Hugh Hefner, Kimberly Conrad, Martson Hefner, and Cooper Hefner - American Society of Magazine editor's awards on April 29, 1998

  Tina Jordan - May 8, 2003

  Izabella St. James - "Redline" (2003) Los Angeles Premiere on April 12, 2007

  Brande Roderick - March 17, 2007

  Hugh Hefner back when he was dating seven ladies - 46th Grammy Awards on February 8, 2004

  And then there were three: Kendra Wilkinson, Bridget Marquardt, Holly Madison - National Lampoon's A Night of Fantasy with The Girls Next Door & Ludacris on September 6, 2008

  Kendra Wilkinson - February 4, 2008

  Bridget Marquardt - June 30, 2007

  Holly Madison - October 4, 2008

  Holly Madison, once Hugh Hefner's primary girlfriend is now with Illusionist Criss Angel - October 31, 2008

  Hugh Heffner's new girlfriends Karissa Shannon and Kristina Shannon - October 13th, 2008

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