After Rory is accepted to the prestigious Chilton Preparatory School, Lorelai is forced to go to her wealthy parents for financial assistance. Her parents happily loan their daughter the money in exchange for an end to the estrangement and a family dinner every Friday night. Unfortunately, things hit a snag when a cute new transfer student flirts with Rory, leading the younger Gilmore to wonder whether leaving Stars Hollow High is really what she wants.

Lorelai oversleeps on Rory's first day at Chilton, and discovers that all her good clothes are at the cleaners. She throws on a tiny tie-dyed top, Daisy Mae 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 some awkward moments in the headmaster's office, bickering the entire way out. Rory's day goes downhill from there. She's handed a three inch binder containing one week's worth of notes from one class and meets some insufferable classmates who are determined to make her life at Chilton miserable.

When Rory announces at Friday night dinner that she has to pick a team sport to play at Chilton, Emily insists that Richard take Rory to the club and teach her golf. Although Rory tees off to a rocky start, she soon gets into the swing of things and has a great time walking and talking with Richard. Later, Lorelai's mixed feelings as Rory tells her how much she enjoyed being with Richard at the club provokes her into an intensely stupid argument with Rory, which is soon patched up when Lorelai realizes that she's not losing Rory to her parents. At the Inn, Lorelai has her hands full overseeing all the preparations for an ornate double wedding ceremony and contending with a pair of spoiled and quarrelsome twin brides, their exhausted mother, their twin grooms, Michel, and the rest of her staff.

Max Medina gives Rory the first ""D"" of her life on an English paper. Paris taunts her non-stop about being a failure and gets Rory very stressed about an upcoming test on Shakespeare that will count for 20% of her English grade. Lorelai spends the week helping Rory study, and they both collapse exhausted at the kitchen table in the early morning hours of the day of the big test. Naturally, they oversleep. In her panic to get to school on time, Rory gets into a car accident -- she gets hit by a deer who runs into Lorelai's car at a stop sign. When she walks into class late, Max tells her that she can't take the test, and Rory has a meltdown, finally giving Paris and Tristan the chewing out they so richly deserve. Lorelai pleads Rory's case with the headmaster to no avail, and has her own meltdown, leaving with a few not-so-well-chosen insults to the headmaster and Chilton. On their way home, Rory insists that they stop and look for the deer to make sure it's all right and Loralei rea