Hugh HefnerMarried (1988-1999) REF
Marilyn Monroe
Jessica Hahn
Brandi Brandt
Suze Randall
Brande Roderick
Holly Madison
Jessica Burciaga
Serena
Heather Kozar
Dalene Kurtis
Bridget Marquardt
Kendra Wilkinson
Marilyn Cole
Constance Money
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
Rod StewartDated (1999) REF
Carole Mallory
Cyrinda Foxe
Rachel Hunter
Britt Ekland
Bobbie Brown
Bebe Buell
Sabrina Guinness
Queenie Glam
Kelly LeBrock
Jo Jo Laine
Susan George
Caprice Bourret
Vicki Hodge
Alana Stewart
Dee Holland
Teri Copley
Stephanie La Motta
Luciana Gimenez
Shray Mecham
Joanna Lumley
Jilly Johnson
Kathy Simmonds
Kim Moon McLagan
Michelle Johnson
Angelica Bridges
Liz Treadwell
Kelly Emberg
Robbie Mantooth
Tracy Tweed
Susannah Boffey
Dee Harrington
Marcy Hanson
Helen Fairbrother
Vicky-Lee McIntyre
Penny Lancaster
Vicky-Lee Valentino
Quincy JonesDated (2005) REF
Naomi Campbell
Billy Eckstine
Lionel Hampton
Nastassja Kinski
Peggy Lipton
Juliette Greco
Devon Wilson
Maryam D'Abo
Hazel Scott
Marpessa Dawn
Jeri Caldwell
Ulla Andersson
Carol Reynolds
Mickella Tupta
Lisette Derouax
Heba Elawadi
John MoranMarried (1999) REF
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Magic Johnson
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