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Rory has a difficult start at the highly competitive Chilton, receiving her first ever D on a paper in Max Medina's English Literature class.After receiving the D, Rory spends hours studying for a Shakespeare exam for which she ends up being late, due to the fact that a deer hit her car, and was not allowed to take the exam.While she is commended for her hard work as a writer, somehow never realising that maybe this is not the profession for her.This could be attributed to the enormous expectations her grandparents and, inadvertently, her brilliant mother, have put on Rory, as well as Rory's biggest wish: to emulate her mother.
Rory accepts the condition, and she also reinstates their weekly Friday night dinners (which had ended when Lorelai paid back the money she owed her parents for Chilton).
Rory's story is mainly told through her studiousness, harnessed by her mother from an early age and by no means forced or rejected by Rory, but rather embraced as almost a sole identifying characteristic.
She spends her first year of high school attending the local Stars Hollow High School with Lane, but is accepted to the prestigious Chilton which can improve her odds in getting accepted Harvard, a lifelong dream of Rory's.
It wasn't until she began school at Chilton that her grandparents became a regular presence in her life.
Her father was rarely around during her childhood years.
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Rory is defined by her mother's decision to leave her parents and their wealthy life behind, as Emily, Richard and Lorelai herself, put the expectations of a "great future" (the one the three of them imagined for Lorelai) on Rory's shoulders.