1×01: Rory is accepted to Chilton Preparatory School, a prestigious private school with a large tuition attached. Lorelai is forced to reconcile with her parents in order to gain their help paying for Chilton. In return, Lorelai and Rory agree to Friday night dinners. Rory also meets Dean, a new student at Stars Hollow High, who leads her to question whether or not she wants to change schools, resulting in an argument with Lorelai.
1×02: Rory enters her first day at Chilton. However, the day doesn’t go well for either Rory or Lorelai. Rory is quickly overwhelmed by her new school, and ends up making her first enemy in Paris Gellar. Lorelai, on the other hand, has issues setting the example for Rory and herself and has a run-in with Emily in the headmaster’s office. Lorelai stands up to Emily about being able to provide a good life for Rory on her own.
1×03: Emily encourages Richard to take Rory to the club to golf for an afternoon, where Rory realizes that she and her grandfather have much in common. Meanwhile, Lorelai is busy planning a wedding at the inn and gets worried when she sees Rory starting to enjoy the life she ran away from.