Sherman is a recent college graduate who works at a bookstore and lives with Jane and Stephen in Brooklyn. His best friend is Ed, his old roommate from college. At the beginning of the story, Sherman is recovering from a break-up with the only girlfriend he’s ever had, a hippie named Sally.
During the course of the series, Sherman tries to become a published writer and strikes up a rocky relationship with a woman named Dorothy (who, to his annoyance, is a moderately successful writer herself). Sherman ultimately is a man with with lofty ambitions, but no real talent to back it up. He eventually moves in with Dorothy after cheating on her, drifts apart from his friends, and becomes a clerk at a music store chain.