A T-shirt, shorts and cowboy boots clad Lorelai accompanies Rory on her first day at school, drawing disapproving stares from the other mothers and from Lorelai's own mother, Emily. Lorelai and Emily argue over money for Rory.
Rory has trouble getting good grades at her new school. Lorelai becomes interested in Rory's handsome teacher.
Rory turns down two boys' offers to take her to a school dance and instead chooses to go with Dean. Dean gets into conflict with the two jealous boys who were rejected by Rory.
Rory gets upset at Emily, who plans a formal birthday party for her but feels that Rory is being ungrateful when Rory reveals that she would not like to have a formal birthday party. However, Lorelai's party for Rory is a success.
Paris exposes the relationship between Lorelai and Rory's teacher, Max, causing a scandal. Lorelai and Max sadly part.