As graduation from Chilton Academy approaches, Rory's life becomes complex, her lifelong dream of attending Harvard at odds with her grandparents' wishes for her to attend Yale. Rory and Lorelai deal with Rory's transition from high school to university, as both of their love lives grow chaotic. Lorelai's attraction to Luke remains hidden with the appearance of old flames and new, including Christopher, Rory's father; Max, Rory's English teacher; and the divorced Alex. Rory's relationship with Dean is strained by her growing attraction to Jess, Luke's rebellious nephew. Will Jess's rebellious attitude be too much for Luke to handle?