Initially working as a receptionist and secretary at Playboy's headquarters in Chicago, she rose to the position of assistant cartoon editor at the magazine.
Cynthia dated Hugh Hefner in the early 1960s, but chose to leave him when he decided that he did not want to get married to her (or, at that time, to anyone else).
Cynthia attended Wright Jr. College, in Chicago, IL, at least for the semester January 1959 - June 1959.