Picaresques experiments with documentary and fictional structures, weaving portraits of three seemingly disparate protagonists together to ultimately create a film about the act of making something. The filmmaker sets out to make a movie about Catalina de Erauso, a nun-turned conquistador from the 16th century who wrote a memoir called Lieutenant Nun. She quickly becomes side-tracked, however, by a relationship she develops with a 10-year old through the process of casting, and the film turns in on itself. Multiple strategies and media are employed to challenge the binary notions of documentary and fiction.