Rob Gordon (John Cusack) reaches a point in his life where he is questioning his priorities. His girlfriend Laura (Iben Hjejle) leaves him for another guy and Rob starts to question why by looking back at several of his past failed relationships. Rob tries to talk this out and get the opinions of some of his ex girlfriends. He also confides in his best friend Barry (Jack Black) who seems to have issues of his own. Much of the talking takes place in the record store that Rob owns. A lot of the dialogue is about music. Rob searches for meaning through music and through the words of his close friends. Rob realizes he must make a decision. Does he need to grow up and change his priorities or are his priorities just fine the way they are? He tries to get answers in several of his past girlfriends but he doesn't really get any clear answers and his ex girlfriends remember things much differently than he does. Rob seems to realize he may have been more at fault than he originally thought. He gets a little desperate and makes an emotional effort to win Laura back.