Rob Gordon owns a record shop in Chicago, where he sells music the old-fashioned way - on vinyl with two wacky assistants, the funny rock snob Barry and the more quietly opinionative underachiever Dick. But the music shop's business isn't the only thing in his life that's going shaky - when his longtime girlfriend Laura breaks up with him, Rob is forced to reevaluate his five unsuccessful attempts at love, including the processsing one.