What is this look for John Cusack, that we've not seen before? He looks...haggard, aged. He's not yet 34 years old, so I assume it's an effect for the part. He plays an adult (Rob) who's never grown up, never matured beyond his infatuation with old records. He can't sustain a relationship because he's too in love with his collection of vinyl, or so it would seem.
Cusack spends a good portion of the movie talking directly to the camera, telling us about his miserable love life. There's no real wit involved in this, and it quickly becomes trite, even boring. Rob owns a used record store that is the fiefdom of one of his employees, a fellow (Barry) who is a thoroughly obnoxious music snob (we're supposed to love him because his insults are "rapier-like," and because he can sing R&B). The other employee is perhaps the only sympathetic character in the picture, and he's so mild-mannered that you feel he's going to dry up and blow away under the force of Barry's tirades. All this makes for what might have been a pretty good sitcom, but the picture dwells too much on Rob's belated coming of age for the comedy to develop.
As Rob tries to reconcile with his latest ex, the picture drops a bomb of a character on us: Ian, played by Tim Robbins, who should be ashamed. The character is pure cliche, a sort of hippie anachronism who actually has sitar music playing in the background over dinner. Ian is a prop, a bit of comic relief who isn't funny. He's there so the girlfriend can say "what was I thinking?"
Ultimately you don't particularly care that Rob comes to realize that it's his inability to commit that keeps ruining his relationships with women. How many times have you seen this theme done? It's one more "dumb guy wises up" movie, with nothing much to distinguish it from all the others.