In London for his daughter's wedding, a struggling jingle-writer, Harvey Shine, misses his plane to New York, and thus loses his job. While drowning his sorrows in the airport pub, Harvey meets Kate, a British government worker stuck in an endless cycle of work, phone calls from her mother, and blind dates. A connection forms between the unhappy pair, who soon find themselves falling in love.

Harvey's Last Night on the Avenue concerns a sensitive young man who joins a group of his friends on a bar crawl the night before he moves from New York back to his hometown in Texas. An obsessive and socially awkward person, Harvey ruminates over many of his minor social faux pas that he perceives as huge errors. As the night goes on, he accrues more and more faults in his mind, and becomes increasingly unable to connect with the people around him.