Hugh HefnerDated (2008-2010) REF
Marilyn Monroe
Jessica Hahn
Brandi Brandt
Suze Randall
Holly Madison
Brande Roderick
Heather Kozar
Dalene Kurtis
Kendra Wilkinson
Jessica Burciaga
Marilyn Cole
Constance Money
Kimberley Conrad
Tiffany Holiday
Shannon Tweed
Sandy Bentley
Stephanie Heinrich
Sandee Westgate
Bridget Marquardt
Dasha Astafieva
Ida Ljungqvist
Joyce Nizzari
Janine Carmen Habeck
Barbi Benton
Karen Christy
Patti Mcguire
Lillian Muller
Terri Welles
Buffy Tyler
Christi Shake
Teri Harrison
Stacy Burke
Zoe Paul
Amanda Paige
Karissa Shannon
Janet Pilgrim
Rae Hefner
Mildred Williams
Joni Mattis
Gale Olson
Carol Imhof
Daina House
Sondra Theodore
Candy Loving
Carrie Leigh
Marina Baker
Amanda Bentley
Katie Lohmann
Jessica Paisley
Kimberley Stanfield
Regina Lauren
Cathi O'Malley
Michelle Winchester
Charis Boyle
Cristal Camden
Tina Jordan
Tricia Wertz
Izabella St. James
Lana Kinnear
Sheila Levell
Melissa Dawn Taylor
Crystal Harris
Jenna Bentley
Anna Sophia Berglund
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Magic Johnson
Letizia Ortiz
Isabel Sartorius
Gulnora Karimova
Raoul Bova