By Hook or by Crook

Shy is a transgender man from the small town of Hoxie, Kansas. After his father dies and the family home faces bank foreclosure, he heads to San Francisco with vague intentions of committing petty crimes to raise enough money to save the property. During his travels he stumbles upon Valentine, an eccentric, emotionally volatile adoptee who is being assaulted in a parking lot; Shy intervenes to defend him. Despite Shy's efforts to shake Valentine loose, Valentine attaches himself and follows Shy. The two end up at a bar and later share a motel room, during which Shy lifts Valentine's wallet — an early indicator of his survivalist opportunism. An immediate, unlikely kinship develops between them, and they become partners in small-time crime, pulling petty thefts and scams alongside Valentine's lover Billie to stay financially afloat. The friendship deepens as they navigate poverty, emotional damage, and occasional physical confrontations, each one slowly opening up about their respective trauma. Valentine is also on his own quest: to track down his biological mother, whose identity he has never known. Their criminal escapades eventually draw police attention, and Valentine ends up on a psychiatric hold (a '51-50'), institutionalized and separated from Shy. Devastated and guilt-ridden over the harm his influence has brought on his friend, Shy searches a phone directory and locates the address of Valentine's birth mother. He then engineers Valentine's escape from the institution. The film closes with Shy, Valentine, and Billie arriving at the birth mother's house — leaving their reunion open-ended but hopeful, an ambiguous promise of connection after a life spent on the margins.

Sources: Wikipedia, web search (review/essay sources including Autostraddle, Peterson Reviews, Bain's Film Reviews, TV Tropes)