DEAN: I mean, I’m not going to a fancy school. I don’t have that kind of pressure. I can’t even imagine what that must feel like.
RORY: You could go to a fancy school if you wanted to.
DEAN: I don’t think so.
RORY: Why not? You’re smart.
Rory continues trying to make Dean into something he’s not – he’s an average student who likes playing sport and home mechanics, but she persists in making him read classic literature, and telling him he could get into a private school if he wanted to. On some level, she cannot be satisfied with Dean as a boyfriend if she won’t accept him not being a bookworm and not going to private school.
Dean is too polite to make the obvious comeback: that he doesn’t have rich grandparents who can bankroll his academic dreams. Even Rory, a very good student, couldn’t get into Chilton on a scholarship, so what hope does Dean have of attending a similar school with average grades and no money for school fees?