Rory shares her mother's taste for many of the same things, such as junk food, donuts from Luke's, coffee, film, television and music.
Her father was rarely around during her childhood years.Shortly after starting her sophomore year, Rory starts attending Chilton leaving her best friend Lane Kim behind.During her last days at Stars Hollow High School, Rory meets the new kid in town and her first boyfriend, Dean Forester.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 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).She finishes her first year in the top 3% of her class.
Notably, Rory's rocky beginning at Chilton is shadowed by a group of three girls, Paris Geller heading the trio.
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 had two boyfriends while she attends Chilton: Dean and Jess, but she is single when she graduates. Despite going through her whole life with Harvard as her dream school, Rory decides to attend Yale University where her grandfather was an alumnus.
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.
Chilton Preparatory School Rory attends the prestigious Chilton Prep for the rest of her high school career.