After Rory is accepted at Chilton, an extremely prestigious and expensive prep school, Lorelai's difficulty in raising the tuition money forces her to ask her wealthy parents, from whom she is estranged, for a loan. The elder Gilmores happily loan their daughter the money in exchange for an end to the estrangement and a family dinner every Friday night. In her last week at Stars Hollow High School, Rory meets a very cute new transfer student named Dean, which gives her second thoughts about attending Chilton. When Lorelai discovers that her ambivalence about Chilton centers on a boy, they argue about her future, but after the first Friday night family dinner at her grandparents' house, Rory makes up with her mother and decides to go to Chilton after all when she realizes the sacrifice her mother has made in agreeing to end the estrangement with her grandparents.

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