At a time when black transgender women in America have an average life expectancy of under 40, Gloria Allen's life and story is not only inspiring but seldom seen. The 73-year-old grew up in the 1950s and 60s amid the celebrated "sissy" balls on Chicago's South Side and transitioned from George after high school with the support of the women in her family - her mother Alma, a former showgirl and Jet centerfold who taught her about makeup; her grandmother Mildred, a seamstress who designed clothes for her; and her Great Aunt Fannie, a former "house" slave who taught her etiquette. An intimate portrait of aging, the film captures Gloria's life now, as she dines with fellow residents in her LGBTQ-friendly senior apartment building; turns losing her front tooth into a joke during her stand-up routine at Second City's comedy training center; attends her 53rd high school class reunion and reunites with her prom date; returns to the neighborhood church where she once sang in the boys choir; connects with her former charm school students and other young people; and confesses that she's afraid of dying alone while searching for a man to spend the rest of her life with. The film also features rarely seen archival images of Chicago's Bronzeville neighborhood nightlife and drag balls.