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Dean escorts Rory when she is presented to society at a debutante ball hosted by her grandmother's chapter of the Daughters of the American Revolution. While at Chilton, Rory becomes engaged in a feud with a close academic rival, Paris Geller. Though the two later become friends, the rivalry continues into their university studies. Rory ...
Rory's dream of attending Harvard leads her to Chilton Academy, where she forges relationships with her grandparents and faces academic rivalries, notably with Paris Geller. After graduating as valedictorian from Chilton, Rory chooses Yale over Harvard, majoring in English and pursuing journalism. Her romantic journey includes relationships ...
At school, Rory is explaining to Lane about Chilton when she bumps into Dean Forester, the new kid from Chicago who has been eyeing Rory. They talk and Rory begins to really like Dean. Just how hard she falls for him isn't revealed until later when she tells her mom that she doesn't want to go to Chilton anymore.
As Lorelai tries to figure out a way to pay the private school tuition (Hello, Emily and Richard!), Rory meets her first love interest Dean (Jared Padalecki) while her best friend, Lane (Keiko ...
Dean (redacted) attends to sulk and stare at Rory, but is triggered by Jess, and ultimately dumps Rory. In the end, we get the highly frame-able scene of Lorelai consoling a sobbing Rory on the ...
Chilton hosts a dance, which Rory and Dean attend, thus confirming they are "boyfriend-girlfriend". Emily sleeps over at Lorelai's the night of the dance to care for Lorelai's injured back and see Rory off. After the dance, Rory and Dean accidentally fall asleep all night at Miss Patty's dance school.
By season 5, Rory begins an affair with her first boyfriend Dean (Jared Padalecki) despite his unhappy teen marriage to Lindsay (Arielle Kebbel). While Rory attempts to call off their trysts via ...
Jess pressures Rory into almost having sex with him, leading to a fist fight between Dean and Jess when the former witnesses an upset Rory. Luke begins dating a lawyer named Nicole. Lane Kim, Rory's best friend, starts a band called Hep Alien and tries to convince her strict mother to let her date the guitarist, Dave, all while keeping the band ...