Rory is accepted into the elite Chilton prep school. Lorelai must make amends with her parents to borrow the money for Rory's tuition. Rory has second thoughts about going to Chilton because of a boy at her school.
Rory's first day at Chilton, where she has a confrontation with Paris. Emily tries to install an internet connection at Lorelai's house without asking first.
Rory goes golfing with her grandfather and surprisingly has a good time. At Lorelai's inn, a wedding is stressing everyone out.
Rory is still playing "catch up" at a Chilton, and Max Medina gives her the first bad grade she has ever received. When she oversleeps on the day of a test everything goes wrong for her.
Lorelai and Max finally decide to date. But Babette and Morey's cat Cinnamon dies and the whole town comes to together to mourn.
It's Rory's birthday. She gets two parties. An elegant and horrible affair thrown by her grandmother and an informal fun party thrown by Lorelai.
Rory gets her first kiss from Dean. The whole town is buzzing about it, yet Rory has not told Lorelai. When Lorelai finds out she invites Dean over for movie night.
It's snowing. Rory is stuck at her grandparents. Max is stuck in Stars Hollow, so he and Lorelai can finally have their first date. Lane feels left-out of Rory's life.
Rory and Dean attend a formal dance at Chilton. Emily takes care of Lorelai who has a back injury. After the dance Rory and Dean fall asleep at Miss Patty's leading to fights between Emily and Lorelai and Lorelai and Rory.
Lorelai is not invited to her parent's Christmas party. At the party Richard collapses and is rushed to the hospital. Luke drives Lorelai to the hospital where everyone is worrying about Richard.
As the relationship with Rory's teacher Max grows more serious, Lorelai panics and decides to end it, but her attempt to break up with him during Parent-Teacher night at Chilton causes even more trouble at school for Rory.
Two double dates. Rory and Dean set up Lane with Dean's friend and the four go out. Meanwhile Sookie and Jackson's first date includes Lorelai and Jackson's cousin, who's very very weird. Lorelai does not enjoy the evening.
Lorelai gives Rory, Paris, Madeline and Louise tickets to a Bangles concert, but the evening doesn't go quite as planned.
Rory and Dean fight, because Dean likes the idea of a 50s type house wife. Rory ends up pretending to be such that type of woman for an evening.
Christopher visits the Hollow for the first time and Rory shows him off and shows him the town. Dinner with the parents ends up with both Rory's grand parents fighting. After talking up his business venture, Lorelai gets Christopher to admit he's failing and has him proposing before leaving town.
It's Rory and Dean's 3-months anniversary, and he plans a special surprise, but it doesn't quite go as he planned. Luke's old girlfriend, Rachel, turns up.
Rebounding from a fight with Dean, Rory ends up kissing Tristin at a party, while Lorelai follows her own impulse to show up at Max's house for a night of passion.
Lorelai's paternal grandmother arrives from England and stresses Emily out in a big way.
Rory takes her grandmother around Stars Hollow for a day. She's horrified to see where Lorelai and Rory first lived.
Lorelai and Max start dating again. After a fight with Lorelai, Rory spends the night at her grandparent's house. Lorelai confronts Dean about the break-up.
In one of the highest rated shows, Lorelai is becoming seriously involved with Max just as she finds herself getting in the middle of another relationship when Luke's girlfriend Rachel accuses him of being in love with Lorelai. Meanwhile, Rory has her own romance drama and tries to work up the courage to win Dean back.