When Rory is accepted to Chilton, an expensive prep school, Lorelai has to ask her estranged parents for money. They agree to pay Rory's tuition, but in exchange, Rory and Lorelai must eat dinner with the Gilmores every Friday night.
Rory oversleeps and is almost late for her first day at Chilton. She arrives just in time to get a thick orientation binder, a cold stare from an obnoxious classmate, and a stern look from her grandmother.
When Rory is requiered to participate in a team sport, Emily insists that Richard take her to the club to learn how to golf.
Rory is off to a rough start at Chilton. She gets a "D" on her first assignment. Lorelai helps her study for her next big test, but when test day comes, Rory hits a deer on her way to school and is late. Lorelai throws a fit when she learns that Rory is not allowed to take the test do to her tardiness.
Lorelai contemplates dating Rory's teacher. Meanwhile, when the neighbor's beloved cat, Cinnamon, dies; a wake is held.
Emily throws Rory a birthday party on Friday while Lorelai throws one on Saturday, but when Emily invites Rory's classmates to her party, Rory is mortified and blows up at her. Rory then tries to smooth things over with her grandmother by inviting Emily to the party on Saturday.
Lorelai finds out that Rory kissed Dean and didn't tell her about it. Feeling hurt, she invites Dean over to watch movies and to get to know him better, which mortifies Rory.
Lane is convinced she's found her soulmate. A snowstorm strands Rory at her grandparents' house and Lorelai spends the night with Rory's teacher. The townspeople brave the snow and reenact a Revolutionary War battle. Featured Music: Rickie Lee Jones.
Rory asks Dean to a formal dance at Chilton and Lorelai makes her a dress. The evening is ruined when they fall asleep together after the dance, leading to a fight between Lorelai and her mother. Part 1 of 2.
Lorelai is uninvited to her parents' annual Christmas party, but she becomes frantic when she finds out her father has collapsed. His close call makes everyone confront their resentments and misunderstandings. Part 2 of 2.
Paris gets upset over the fact that her parent's divorce has become public gossip. Lorelai attends Parent's Day at Chilton. Things heat up between Lorelai and Max.
After Lorelai encourages Sookie to ask Jackson out, she finds herself on a double date with Jackson's weird cousin. Rory and Dean go on a double date with Lane and Todd, Dean's friend, but it turns into a disaster when they don't tell their moms about it. Lorelai studies for a test in her business class.
Sookie gets tickets to see the Bangles with Rory but ends up giving them away to Rory and her friends.
Dean makes himself very unpopular when he admits that he likes the idea of having a doting housewife. Lorelai asks for Luke's help to search for a missing chick. Rory's father comes to town.
Rory's father, Christopher, rides into town to surprise the Gilmore Girls. His visit gets Rory excited but Lorelai worries about how his wandering ways will effect their daughter.
Rory's boyfriend, Dean, professes his love for her. Lorelai suffers through dinner with her parents and a man they have invited as her blind date.
Rory tries to be strong to deal with the aftermath of Dean breaking up with her and ends up kissing Tristin at a party. Lorelai shows up at Max's for a night of passion.
Great Grandma Gilmore comes in from London and offers to set up a trust fund for Rory's education, causing Emily to worry about the possibility of their financial independence from her.
After spending the day traveling through Rory's childhood past, Emily is inspired to create a world for her that includes the material things she never had as a youth.
Rory runs to her grandparents house after fuming over the fact that Lorelai has been seeing Max again, and that Dean and Lane have been studying together, making Lorelai wonder if she's turned her daughter into a commitment-phobe.
As Lorelai's romance with Max gets serious, Luke's girlfriend begins to think that Luke is really in love with Lorelai. Meanwhile, Rory makes an attempt to win Dean back.