I don't want to make it sound like a hotbed of lesbianism but I did have a number of relationships.

O'Leary then moved to New York City and did doctoral studies in organization development at Yeshiva University. During that period Jean O'Leary became involved with the nascent gay rights movement joining the Gay Activists' Alliance (GAA) Chapter in Brooklyn and later lobbying state politicians. She co-founded National Coming Out Day with Rob Eichberg in 1987.

She had been a Roman Catholic Religious Sister before this involvement and would later write about her experience in a 1984 anthology Lesbian Nuns: Breaking Silence.