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Posted on Dec 30, 2010

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!

by PopularNobodies

Community Contributor

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