Teal Redmann

Lorelai oversleeps and accompanies her daughter to prep school wearing cut-off jeans and cowboy boots; Rory antagonizes Chilton's top student.

Rory has trouble getting good grades at her new school. Lorelai becomes interested in Rory's handsome teacher.

Emily throws an elegant birthday party for an embarrassed Rory, who blows up at her grandmother; Rory later invites her grandparents to a wild party.

Rory and Dean fall asleep together following a fairytale evening at a formal dance, leading to a blowout between Lorelai and her mother over discipline.

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