Louis Ives is a lonely dreamer who fancies himself the hero of an F. Scott Fitzgerald novel. When a deeply embarrassing incident forces him to leave his job at an exclusive Princeton prep school, Louis head s to New York City to make a fresh start. He quickly finds a 9 to 5 job at an environmental magazine, where he encounters an entrancing, green-obsessed co-worker Mary. But, what really sparks Louis' imagination is his new home life. He rents a room in the ramshackle apartment of Henry Harrison, a penniless, wildly eccentric failed playwright. When Henry’s not dancing alone to obscure music or singing operettas, he's performing ¿ with great panache — the duties of an "extra man," a social escort for the wealthy widows of Manhattan high society. The two men develop a volatile mentorship, which leads to a series of urban adventures -- encountering everything from a leaping lion to a wildly jealous hirsute neighbor to drunken nonagenarians to a shady Swiss hunchback.