In 1970’s Cambridge, Massachusetts, Steve and his roommate George live together after they graduate from Harvard University. Steve, an occasional substitute teacher, spends most of his time at the library, where he reads Marxist critical theory and obsesses over the prospect of an oncoming socialist revolution. George is a more vagrant character, and spends the days high on acid and pot. One day, while Steve and George are at home — where Steve lays in an orange lifeboat in the center of their living room and George sits in his room contemplating his failing success, George tells Steve that he’s going back to school to get a master’s degree. Later that evening, Steve and Susan — a fourth-grade teacher and Steve’s girlfriend — discuss leaving Cambridge “before it sinks,” at Steve’s insistence that Cambridge’s political and social climate is suffocating. He suggests that they immigrate to Quebec or Ontario, but Susan is tentative, and argues that Steve would have to participate in politics to escape them — a glib jab at Steve’s Marxist delusions of grandeur. The next day, after a morning spent at the library, Steve and George meet for lunch, where George shares with Steve that he will pursue a MA in English and work at a publishing house with help from his uncle. After lunch and a phone call with Susan, Steve visits a bookstore who’s manager turns out to be a friend from college, Phil, who shares with Steve that he wants to open his own bookstore in Vermont with help from his uncle. Later and back at home, a conversation with George about Phil’s life and his uncle who would help him like George’s uncle would him sends Steve into a depression in his lifeboat, where he has a psychedelic-esque vision which involves tiger-sized parrots, stoned policeman, and a fire in a subway car. Afterwards, Steve and Susan go out for dinner at the neighborhood food co-op. The next day, George and Steve discuss their friend Lynne, a recovering drug addict who had spent the night at their place after her partner kicked her out. They share a sense that Lynne is a "casualty" in the war of a hard life and, after they agree that they don't want to be casualties too, decide to take the orange lifeboat to sail on the Charles River. They sail along the river until they reach the school where Susan works. They pick her up and continue to sail, and Steve notes on that the revolution he imagined in his head is a childish fiction unfounded in reality. They return home, where George cleans his disgusting room and Steve deflates the orange lifeboat — decisive in their new maturity.