Caroline Macfarlane sets out to make a documentary about Jane Marx, a wildly eccentric New Yorker. Marx has worked as a Manhattan tourist guide for thirty-eight years, and she’s no shrinking violet. Her offbeat sense of humor and larger-than- life personality are front and center as she guides Caroline through New York City in the opening scenes. But when the filmmaker and subject sit down for their first on-camera interview, they discover that they have a sadness in common. They both lost brothers to whom they were very close. Jane’s brother, Paul, died of AIDS in 1989; Caroline’s brother, Blake, died of leukemia in 2018, and this shared tragedy becomes the basis of their friendship and the subject of the film.