In 1948, the summer after Kay graduated from Withrow High School in Cincinnati, she met Jane, a girl who had gone to the same school. She fell in love with her and Jane fell in love with Kay. Jane had had a little experience, so they very quickly developed a physical relationship. For a year Kay thought it was the world's greatest friendship.

After a year together Kay finally faced the fact that this was more than friendship. This was desire and sex and lust and love, just like straight people feel.

After the breakup with Jane, Kay moved to Boston and went to work for the Christian Science Monitor. Several years would pass before she put the relationship behind her and began searching for other women like herself. It was a search that would lead her into an important role in the gay civil rights effort and in 1961 into a lifelong relationship with Barbara Gittings.