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Her parents, while still loving her a great deal, continue to resent her for this choice.
This results in a significant portion of the conflict throughout the season as Lorelai deals with having her parents in her life on a regular basis for the first time since she was a teenager.
She throws on a tiny tie-dyed top, cutoff shorts, and cowboy boots to the dismay of Rory, the Chilton headmaster, and Emily, who has shown up for Rory's first day.
Lorelai and Emily leave after an awkward conversation in the headmaster's office, bickering the entire way out. She's handed a three inch binder containing one week's worth of notes from one class and meets several insufferable classmates who are determined to make her life at Chilton miserable.
The first season of Gilmore Girls introduces Lorelai Gilmore (Lauren Graham) and her sixteen-year-old daughter, Rory (Alexis Bledel), as well as the fictional Connecticut town of Stars Hollow and its many quirky inhabitants.
The central plot point of the season is Rory’s acceptance to Chilton, an elite prep school, and Lorelai’s need to borrow money from her parents, Emily (Kelly Bishop) and Richard (Edward Herrmann), in order to fund her daughter’s education.
The first season of Gilmore Girls, an American Comedy-drama television series, began airing on October 5, 2000 on The WB television network.
Lorelai has no love interest when the series begins, but she soon develops feelings for Rory’s English teacher at Chilton, Max Medina (Scott Cohen).
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.
Lorelai oversleeps on Rory's first day of Chilton, and discovers that all her good clothes are at the cleaners.
Lorelai also briefly reunites with Rory’s father, Christopher (David Sutcliffe), but turns him down when he asks her to marry him.
Lorelai and Max reunite toward the end of the season, and he proposes in the season finale. James (Melissa Mc Carthy), the chef at the inn she manages.
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Lorelai’s parents lend her the money, but on one condition: she and Rory must attend dinner at their home in nearby Hartford every Friday night until the loan is repaid.