Based primarily on the Nick Hornby novel rather than the subsequent film version it inspired, the plot focuses on Rob Gordon, a Brooklyn record shop owner in his thirties obsessed with making top five lists for everything, always observing rather than participating in life.

When his girlfriend Laura leaves him, he goes through a painful re-evaluation of his life and lost loves (with a little help from his music) and he slowly learns that he has to grow up and let go of his self-centered view of the world before he can find real happiness.