No matter how classic this film is, it's hard to shake the feeling that Andie and Blane are dating an idea of a person rather than the actual person. Blane's bored of his yuppie rich boy life, so naturally he goes for the eccentric girl from the wrong side of the tracks. And it has to be immensely flattering for Andie when someone from the group that had always picked on her is actually kind and interested in her as a person. But is there a real, solid connection between these two characters? Not really. It doesn't help that Blane is probably one of the most bland characters in the history of cinema, and that Jon Cryer immensely overshadows him in the doting best friend role. But it just seems like they're in this relationship for all of the wrong reasons. They come off as people who are dating because, as generally good people, they're nice to each other, not because there's any attraction going on between them. It speaks volumes that a tremendous portion of the audience wanted Andie and Duckie to end up at the prom together.