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Episode Guide
Pilot (10/5/00) -  Lorelai reluctantly asks her estranged parents for financial help when Rory is accepted at an expensive private school. Her parents agree to lend her the tuition money - but at a personal cost.

The Lorelais' First Day at Chilton (10/12/00) -  Lorelai oversleeps on the morning of Rory's first day at Chilton. The hurried woman dresses in casual clothes, only to find her own mother waiting in the headmasters office. Lorelais' attitude draws sharp criticism from the elder Gilmore, and dirty looks from the other students' parents.

Kill Me Now (10/19/00) -  Emily badgers Richard into taking Rory to their country club for golf lessons after the grandparents learn that Rory's required to join a school sports team. Meanwhile, Lorelai oversees the double wedding of a set of spoiled twin brides.

The Deer-Hunters (10/26/00) -  After recieving a bad grade on an English paper, Rory tries to prepare for a major test on Shakespeare, only to find a bored Lorelai nagging her for attention. Elsewhere, Sookie broods over a review from a magazine's food critic.

Cinnamon's Wake (11/2/00) -  Rory has an embarrassing encounter with Dean on a bus ride to school. Lorelai is courted by Rory's English teacher, who asks her out during a bake sale at Chilton. At the Inn, Michel deals with a group of enthusiastic group of French clients.

Rory's Birthday Parties (11/9/00) -  Emily insists that Rory's birthday party takes place at the elder Gilmores' home and then asks Lorelai for help in finding a special gift for her granddaughter. But Rory is horrified to discover that her grandmother sent part invitations to her classmates.

Kiss and Tell (11/16/00) -  Rory doesn't tell her mother about her first kiss with Dean, and a vexed Lorelai embarrasses her daughter by inviting Dean over to the house to watch videos.