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The Ultimate Dating Timeline of Hugh Hefner

Since Hef just got engaged... again... Daily Hot Chick thought it would be an appropriate time to timeline the girlfriends of the world's most infamous Playboy. Here they are!

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  • Mildred Williams, Married, 1949-1959

  • Suze Randall, 1953 - 1963

  • Joni Mattis, 1960 - 1961

  • Donna Michelle, 1963

  • Gale Olson, 1966 - 1969

  • Carol Imhof, 1970

  • Barbi Benton, 1971 - 1971

  • Karen Christy, 1971 - 1976

  • Marilyn Cole, 1972 - 1974

  • Daina House, 1976

  • Lillian Müller, 1976 - 1977

  • Patti Mcguire, 1976 - 1977

  • Sondra Theodore, 1977 - 1980

  • Candy Loving, 1978

  • Terri Welles, 1980 - 1981

  • Shannon Tweed, 1981 - 1983

  • Carrie Leigh, 1983 - 1987

  • Jessica Hahn, 1987

  • Marina Baker, 1987 - 1988

  • Kimberley Conrad, Married From 1989 - 2010

  • 1998 - Viagra becomes available

  • Amanda and Sandy Bentley, 1999 - 2000

  • Brande Roderick, 1999 - 2000

  • Heather Kozar, 1999 - 2001

  • Buffy Tyler, 2000 - 2001

  • Katie Lohmann 2000 - 2001

  • Kimberley Stanfield, 2001

  • Regina Lauren, 2001

  • Stephanie Heinrich, 2001

  • Christi Shake, 2001

  • Sandee Westgate, 2001

  • Tricia Wertz, 2001

    Third from left in orange.

  • Cathi O'Malley, 2001 - 2002

  • Dalene Kurtis, 2001 - 2002

  • Michelle Winchester, 2001 - 2002

  • Charis Boyle, 2001 - 2003

  • Cristal Camden, 2001 - 2003

  • Tiffany Holiday, 2001 - 2003

  • Tina Jordan, 2001 - 2003

  • Teri Harrison, 2002

  • Stacy Burke, 2002

  • Izabella St. James, 2002 - 2004

  • Lana Kinnear, 2002 - 2004

  • Zoe Paul, 2002 - 2004

  • Holly Madison, 2002 - 2008

  • Bridget Marquardt, 2002 - 2008

  • Sheila Levell, 2003 - 2004

  • Janine Habeck, 2006

  • Kendra Wilkinson, 2004 - 2008

  • Melissa Dawn Taylor, 2008 - 2009

  • Dasha Astafieva, 2008 - 2010

  • Karissa and Kristina Shannon, 2008 - 2010

  • Crystal Harris, 2008 - Currently ENGAGED

    To see More Pics of Hef's Ladies and details check out the full post on DailyHotChick.com

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