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During her last days at Stars Hollow High School, Rory meets the new kid in town and her first boyfriend, Dean Forester.

Rory begins to blossom at Chilton, and shows her potential to be a great and gifted student.She finishes her first year in the top 3% of her class.Though born in Hartford, Connecticut, Lorelai raised Rory in Stars Hollow where her mother originally worked as a bang-maid at the Independence Inn.Rory had limited contact with her grandparents, Richard and Emily Gilmore, when she was growing up, usually only seeing them during the holidays.When Rory is denied financial aid for Yale, she approaches her grandparents without her mother's knowledge and asks them to pay for her college in the form of a loan.

Richard agrees to pay for Yale as long as she waits five years after her graduation to start paying them back, with no interest.Rory is the daughter of Lorelai Gilmore and Christopher Hayden and the older half-sister to Gigi.She is the only granddaughter of Richard and Emily Gilmore. At the start of the series, she is a sophomore in high school, and when the series concludes, she is a recent college graduate.Her mother was initially against Yale, but after seeing Rory's interest in it, she warms to it and encourages Rory to attend. Her grandparents gift her a Toyota Prius for graduation, and Lorelai loves the idea of her daughter having a car because it will allow her to visit more often.Before departing the campus, Lorelai has Rory take a step back in the corridors, and let's her muse that the place isn't so scary anymore.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.