When you live in Chicago and you're in the 30s, and alone, there is something that starts happening called mid-age crisis. That is what happened to Rob Gordon (John Cusack). He is exactly that type of a guy- alone, in his 30s, owns a record store called Championship Vinyl in the time when records aren't much in usage any more and is trying his best not to be constantly depressed. He also has a couple of workers in his record shop, Dick (Todd Louiso) and Barry (Jack Black), who he hired to work three days a week, but they started showing up every day four years ago. He knows his way with records and he is amazing as a DJ, when he gets his hands on the records in the club. But, when it comes to dating, he has no clue. After five break ups, he is still searching for the right woman. Throughout the movie we see him pining over his last girlfriend, Laura (Iben Hjejle), who left him for a pretty strange dude called Ian (Tim Robbins). As he makes a list of his girlfriends, he decides to contact every one of them and that makes him learn a lot about himself along the way. And growing up isn't actually a nice sight for him.