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.
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 and Max start dating again. After a fight with Lorelai, Rory spends the night at her grandparents' house. Lorelai confronts Dean about the break-up.
Lorelai hesitates to tell her parents about her engagement to Max, despite Rory's urging. Rory and Dean have a spat over Rory's plans for extracurricular activities.
Lorelai's well-intentioned advice falls on deaf ears when Luke reluctantly takes in his wild 17-year-old nephew Jess, while Rory finds herself attracted to the town's newest resident.
Lorelai and Sookie have the first fight of their long friendship when, upon hearing that the Independence Inn may be sold, Lorelai panics and decides that their shared dream of opening an inn together is doomed to failure.