Hugh HefnerDated (2001-2002) REF
Marilyn Monroe
Jessica Hahn
Brandi Brandt
Suze Randall
Brande Roderick
Holly Madison
Jessica Burciaga
Serena
Heather Kozar
Bridget Marquardt
Kendra Wilkinson
Marilyn Cole
Constance Money
Kimberley Conrad
Susan Nero
Joyce Nizzari
Shannon Tweed
Sandy Bentley
Sandee Westgate
Stephanie Heinrich
Dasha Astafieva
Ida Ljungqvist
Mildred Williams
Barbi Benton
Karen Christy
Patti Mcguire
Lillian Muller
Terri Welles
Buffy Tyler
Christi Shake
Zoe Paul
Teri Harrison
Stacy Burke
Amanda Paige
Janine Carmen Habeck
Karissa Shannon
Rae Hefner
Janet Pilgrim
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
Tiffany Holiday
Izabella St. James
Lana Kinnear
Sheila Levell
Melissa Dawn Taylor
Crystal Harris
Kristina Shannon
Crystal Hefner
Amy Leigh Andrews
Jenna Bentley
Anna Sophia Berglund
Shera Bechard
Nick CarterDated (2006) REF
Paris Hilton
Tila Tequila
Ashlee Simpson-Wentz
Brittny Gastineau
Willa Ford
Haylie Duff
Anastacia Newkirk
Anastacia
Malika
Bai Ling
Kaya Jones
Kari Ann Peniche
Alex Murrel
Julie Bornemann
Debbie LaFave
Nada Veselinovic
Tanya Jane
Javine Hylton
Irina Voronina
Kim Martin
Lauren Kitt
Myriam Lamontagne
Debra Lafave
Tiffanny Mannik
Asun Ortega
Sue Bird
Isabelle Filling
Angi Taylor
Alisa Reyes
Christy Lane
Alexandra Bachelier
Celiece Aurea
Sara Borough
Nikki Chick
Claire Grieve
Irina Pushistaya
Khierstin Nichole
Bryttny Scheibe
Antonella Barba
Sandy Babe
Meredith Weiss
Daiana Ocampo
Marina Poldervaart
Kristen Kukta
Christina Uhrenholt
Meghan Kabir
Alexie Phillips
Lys Lawrence
AJ McLeanHookup (2003) REF
Alycen Rowse
Shauna Sand
Summer Altice
Amanda Latona
Kaci Brown
Casey Raye
Shelly Martinez
Karen Simpson
Stephanie Hirsh
Marisa Jackson
Kristin Denehy
Sarah Martin
Wendy Rice
Rochelle McLean
Michael McmahonHookup (2003) REF
Cynthia Kirchner
Cara Zavaleta
Martha Byrne
Christina Kotalik
Jenni Croft
Mike McMahonHookup (2003) REF
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