At the dance they talk about Dean's height and he says he is 6'2". Jared Padalecki, who plays Dean & is 19/20 years old at the time, is actually 6'4".
During the confrontation scene between Tristan and Dean, Caesar from Luke's diner can be seen in the background. It's unclear if he's playing another character at this time. Or if Caesar also attended Chilton. Interesting either way.
Rory is reading the Complete Dorothy Parker. The production company for this show is called Dorothy Parker Drank Here.
First episode not to feature Luke Danes
Dean tells Louise that he's 6' 2". Jared Padalecki is in fact 6' 4".