Episode 1
Lorelai must ask her estranged parents for financial help when her daughter, Rory, is accepted into a prestigious prep school.
Episode 2
Lorelai oversleeps and accompanies her daughter to prep school wearing cut-off jeans and cowboy boots; Rory antagonizes Chilton's top student.
Episode 3
Rory and her grandfather enjoy a glorious day of golf, making Lorelai feel left out; the inn hosts a double wedding with two sets of identical twins.
Episode 4
Rory becomes obsessive about studying for a Shakespeare exam after she receives her first D grade, but when she misses the exam it leads to a parent-teacher conference.
Episode 5
Rory is flustered around Dean; Lorelai must cancel a date with Rory's teacher to attend Cinnamon's funeral.
Episode 6
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.
Episode 7
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.
Episode 8
Rory is stranded at her grandparents' house by a snowstorm; Lorelai spends the night with Rory's teacher, Max; the townspeople re-enact a Revolutionary War battle.
Episode 9
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.
Episode 10
Lorelai is hurt when she is excluded from her parents' Christmas bash, but she rushes to the hospital after her father collapses at the party.
Episode 11
Lorelai tries to break up with Rory's teacher, Max, on parent-teacher night, which leads to more problems for her daughter at school.
Episode 12
After Lorelai encourages Sookie to ask out Jackson, she finds herself on a double date with Jackson's weird cousin; Rory goes on a double date as well.
Episode 13
Though Lorelai is excited about going to a Bangles concert, she offers the four concert tickets to Rory and three of her new schoolmates.
Episode 14
Lorelai enlists Luke to help find a missing chick; Rory quarrels with her boyfriend over housewifery.
Episode 15
When Rory's father makes an unexpected visit, he awakens long-buried feelings of passion in Lorelai, as well as inspiring anger in Lorelai's parents.
Episode 16
Rory's boyfriend declares his love for her; Lorelai endures dinner with her parents and a blind date.
Episode 17
Rory kisses Tristan at a party after fighting with Dean; Lorelai impulsively shows up at Max's house for a night of lovemaking.
Episode 18
Rory's great-grandmother offers Lorelai a trust fund for Rory's education, causing Emily to fear losing her newfound relationship with them.
Episode 19
A road trip through her granddaughter's past inspires Emily to make up for the material things Rory did not have growing up.
Episode 20
Rory runs to her grandparents' house after discovering Lorelai and Max are dating again; Lorelai discovers the truth behind Dean and Rory's breakup.
Episode 21
Lorelai becomes increasingly serious about Max; Luke's girlfriend accuses him of being in love with Lorelai; Rory attempts to win Dean back.
