Rory is accepted into the elite Chilton prep school. Bad news for Lorelai: she must make amends with her parents to borrow the money for Rory's tuition. The money is available- with strings attached.
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.
Babbette and Morey's cat dies. Lorelai misses her date with Max because of the funeral. She also discovers that Rory is keeping a secret from her, namely Dean.
It's snowing, and Lorelai is giddy. She runs into Max in Stars Hollow, and invites him back to her place. But they run into someone unexpected when they get there. Lane feels left-out of Rory's life.
Rory asks Dean to accompany her to a formal dance at Chilton, but the lovely evening is spoiled when they fall asleep together after the dance, leading to a fight between Rory's grandmother and her mom over who has been a worse mother.
Richard Gilmore is rushed to hospital after collapsing at the Christmas party. Luke goes with Lorelai to the hospital, where Emily and Rory already are.
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.
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-mmonths 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 Tristan at a party, while Lorelai follows her own impulse to show up at Max's house for a night of passion.
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.