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.
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.
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.