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The series pilot indicates that Rory harbours a long-held dream to study at Harvard University, and it is for this reason she transfers from Stars Hollow public high school to the prestigious Chilton Preparatory.

She attends Chilton for her sophomore, junior, and senior years of high school.

Lorelai is forced to ask her parents for help to pay Chilton's tuition fees, ending their relative-estrangement since Lorelai moved out when Rory was a baby.

Rory grows close to her wealthy grandparents, Emily and Richard, although she also comes into conflict with them periodically.

It is evident in the show that Rory and Lorelai share a special bond, and may be even considered best friends.

She begins the journey, but has an epiphany and calls her mother to share a warm recollection of her father; she and Emily reconcile.

Abandoning her plan for the hike, Lorelai returns to Stars Hollow and proposes marriage to Luke, and the two marry in November 2016.

Furthermore, Rory, by this time, has been accepted to Yale, and has been denied financial aid due to Lorelai receiving a one-time investment payout given to her by her father (see below).

Lorelai is ready to divert her money for the purchase and renovation costs to Rory's tuition, but Rory independently turns to her grandparents for help with the tuition, allowing Lorelai and Sookie to purchase The Dragonfly Inn.