Teal Redmann

Rory's first day at Chilton Prep begins badly when Lorelai accompanies her daughter into the intimidating school wearing a T-shirt, cut-off jeans and cowboy boots, an outfit that draws disapproving stares from the other mothers.

Rory kisses Tristin at a party after fighting with Dean, and Lorelai impulsively shows up at Max's house for a night of lovemaking.

Lorelai tries to break up with Rory's teacher Max, on parent-teacher night, which leads to more problems for her daughter at school.

Emily throws Rory an elegant birthday party and invites Chilton students, but Rory is embarrassed that the kids she doesn't get along with have been forced to come to the party by their own wealthy parents.

Dean tells Rory that he loves her; Lorelai suffers through dinner with her parents and a blind date; Luke's old flame returns to Stars Hollow.

Rory's great-grandmother offers Lorelai a trust fund for Rory's education, causing Emily to fear losing her newfound relationship with them.