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 runs to her grandparents' house after discovering Lorelai and Max are dating again, and Lorelai discovers the truth behind Dean and Rory's breakup.

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.

Lorelai is busy rebuilding the inn when Richard surprises her; Luke confirms his fears that Jess is skipping school to work extra shifts at the store.

Still struggling to catch up at Chilton, Rory receives the first `D' of her life on an English assignment and is so humiliated that she plunges into obsessive studying.