Lorelai Gilmore has worked her way up from maid at an inn to running the place, all while being a smart and funny single mom to a smart and funny teenage girl, also named Lorelai, or Rory, for short. Times are happy when 16-year-old Rory gets accepted at Chilton, a private school. They become less happy when Lorelai gets the bill, which means she must borrow money from her rich parents. Worse, her mother resorts to blackmail: in exchange for the loan, Lorelai and Rory must come to dinner once a week. Meanwhile, Rory meets a gorgeous boy at school. He's from Chicago, and he actually got her reference to "Rosemary's Baby". He's also impressed that she loves to read. Now Rory suddenly wants to stay where she is. Will she let a perfectly good plaid skirt go to waste?