Lorelai must ask her estranged parents for financial help when her daughter, Rory, is accepted into a prestigious prep school.

Lorelai oversleeps and accompanies her daughter to prep school wearing cut-off jeans and cowboy boots; Rory antagonizes Chilton's top student.

Rory and her grandfather enjoy a glorious day of golf, making Lorelai feel left out; the inn hosts a double wedding with two sets of identical twins.

Rory becomes obsessive about studying for a Shakespeare exam after she receives her first D grade, but when she misses the exam it leads to a parent-teacher conference.

Rory is flustered around Dean; Lorelai must cancel a date with Rory's teacher to attend Cinnamon's funeral.

Emily throws an elegant birthday party for an embarrassed Rory, who blows up at her grandmother; Rory later invites her grandparents to a wild party.