Teal Redmann

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.

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.

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.

Rory asks Dean to accompany her to a formal dance at Chilton, but the lovely evening is spoiled when they fall asleep together after the dance.

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

Luke takes in his wild 17-year-old nephew Jess, ignoring Lorelai's well-intentioned advice and Rory is drawn to the new guy in town.