Rob Gordon (John Cusack) is the owner of a failing record store in Chicago, where he sells music the old-fashioned way -- on vinyl. Although they have an encyclopedic knowledge of pop music and are consumed by the music scene, it's of no help to Rob, whose needle skips the love groove when his long-time girlfriend, Laura (Iben Hjejle), walks out on him. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.