Teal Redmann

Lorelai tries to break up with Rory's teacher Max, on parent-teacher night, which leads to more problems for her daughter at school.

Rory's first day at Chilton Prep begins badly when Lorelai accompanies her daughter into the intimidating school wearing a T-shirt, cut-off jeans and cowboy boots, an outfit that draws disapproving stares from the other mothers.

Emily tries to reunite Christopher with his family, which leads to an angry confrontation between Rory and her father. Meanwhile, Lorelai wards off the attentions of a geeky suitor.

Luke takes in his wild 17-year-old nephew Jess, ignoring Lorelai's well-intentioned advice and Rory is drawn to the new guy in town.

Rory waits for acceptance letters from colleges; Lorelai shares a passionate kiss with ex-fiance Max and wonders if ending the engagement was the right decision.

Emily throws Rory an elegant birthday party and invites Chilton students, but Rory is embarrassed that the kids she doesn't get along with have been forced to come to the party by their own wealthy parents.