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His ideals on sexual curiosities and interests were not well thought of in his earlier years, as he was at times a topic of controversy. Though he’s 83 years old, he has no shortage of girlfriends and is able to pull off what many men have been trying to successfully do for years – dating more than one woman at a time!Here is a LONG list of Hef’s girls throughout the years.Mary Warren Dated Hefner: In the mid 1960s Occupation: Model Carol Imhof Born: March 13, 1948 Dated Hefner: 1970 Occupation: Model; Worked at the Playboy Club in Chicago Miscellaneous Information: She was Playmate of the Month in December 1970. Suze Randall Born: May 18, 1946 Dated Hefner: In the 1970s Occupation: Photographer, pornographer Miscellaneous Information: She worked for Playboy magazine in the 1970s and is still an active pornographer.Barbie Benton Born: January 28, 1950 Dated Hefner: 1971 to 1974 Occupation: Model, actress, singer Miscellaneous Information: Barbie Benton was never Playmate of the Month, though some people think she was at some point because she appeared on the cover of the magazine several times.

In 2000, she played the role of Leigh Dyer on the hit TV show .

Cathi O`Malley Born: July 27, 1981 Dated Hefner: 2001 to 2002 Occupation: Model Miscellaneous Information: Cathy was Playboy’s Cyber girl of the week for the third week of February 2002.

Dalene Kurtis Born: November 12, 1977 Dated Hefner: 2001 to 2002 Occupation: Model and television personality Miscellaneous Information: Kurtis was Playmate of the Month for September 2001 and was also the Playmate of the Year for 2002.

Donna Michelle Born: December 8, 1945 Died: April 9, 2004 Dated Hefner: 1963 Occupation: Model, actress, and photographer Miscellaneous Information: Donna Michelle was Playmate of the Month in December 1963 and became the Playmate of the Year in 1964.

Gale Olson Born: October 27, 1947 Dated Hefner: 1966 to 1969 Occupation: Model Miscellaneous Information: She was Playmate of the Month in July 1968.

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