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.

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

Headmaster Charleston decrees that both Gilmore girls need to improve their socialization skills at Chilton if they want him to write a glowing recommendation for Rory's Harvard application.

Rory's first attempt to socialize leads her to ask a group of girls at lunch if she could join them. They agree and hit it off famously. After lunch, an insanely jealous Paris accosts Rory and tells her the the group that she innocently stumbled into is ""The Puffs"", Chilton's famed secret sorority. Paris would do anything to join, and she begs Rory not to bad-mouth her to the group. At the next opportunity, Rory talks Paris up to the group and they are both accepted as pledges. The Puffs ""kidnap"" Rory, Paris and the other pledges very early one morning under the guise of taking them to breakfast, but instead take them to Headmaster Charleston's office to be initiated into the group. In the middle of the ceremony, they are discovered by Charleston and the security guards. He calls their parents an

Rory asks Richard for help in creating and marketing a first-aid kit for Chilton's annual Business Fair, which leads him to realize that he is unhappy in retirement and wants to start a second career; fresh from having underbid on Rory's lunch basket and the loss of the bracelet he made for her, Dean goes overboard in trying to be close to Rory, afraid that she is losing interest in him, and finally becomes resigned to her affection for Jess; at first, Michel is ecstatic when his flamboyant mother Giselle visits, but after Lorelai causes problems for him when she reveals to Giselle that Michel has been holding back from his mother, Michel quickly is driven crazy by his mother's incessant questioning.

To Lorelai's horror, Kirk asks her out on a date after being encouraged by Luke; Emily's lunch with Lorelai at Luke's ends badly; Christopher shows up uninvited at Friday night dinner and quarrels with both Lorelai and Rory before Emily asks him to leave; Rory runs into Jess and they each betray their hurt feelings -- Rory about Shane and Jess about not hearing from Rory all summer; and Francie targets Paris and Rory for a world of trouble if Rory doesn't stop Paris from running the student council like a dictatorship.

Luke is opposed to having Taylor's attorney Nicole oversee the paperwork for the construction of the new soda shop until he meets the attractive redhead, who takes as immediate a shine to Luke as he does to her; Lane's clever scheme to get her mother's permission to attend the prom horribly backfires; Luke offers to teach Lorelai the fine art of angling after Alex invites her to go fishing; Rory and Lorelai clear out their garage for Lane's band and Lorelai gains a new admirer from the band; Lane and Rory have some hearts-to-hearts about the men in their lives; Paris's ratcheting up the conflict between her and Rory when she calls for Rory's impeachment by the student council is brought to a swift end by Headmaster Charleston, who threatens to revoke the glowing letters he wrote to Harvard for each of them.

Rory and Paris compete for the honor of speaking at Chilton's Bicentennial; Sookie and Jackson get some very good life (and diaper) changing news; Paris and Rory reconcile; Lorelai runs into Max and it's apparent that they're not quite over each other yet; Paris has a meltdown on national television when she fails to get into Harvard; Rory's college acceptance letters finally arrive; Paris isn't sure what to think about the latest development in her relationship with Jamie.

Rory finally learns her mother can't afford to buy the Dragonfly Inn since financial aid for Yale didn't come through. She decides to take matters into her own hands with a quick visit to her grandparents' right before graduation. Luke has second thoughts about a trip with Nicole after something Lorelai tells him. Jess makes silent contact with Rory after she gives her speech at Chilton.

Miss Patty celebrates forty years in show business on the same day that Luke mourns his father's death; Terrence's urging Paris to get on with her life prompts her to try speed dating, where she hooks up with Doyle; Marty finally clues Rory in that both he and Logan are interested in her; Lorelai's attempt to do something nice for Luke backfires; Rory enlists Richard in turning the practical joke table back on Logan; at Headmaster Charleston's request, Rory happily gives Anna, a Chilton student and prospective Eli, the Yale grand tour, but the immature Anna manages to get both herself and her host in trouble with her party-crazed ways.

After getting into a science camp, April tells Luke that she cannot go on the boating trip with him over the summer. Zach is asked to go on tour with another band. A drunk Lorelai serenades Luke at Karaoke night. Logan gets a job in San Francisco, where he then goes to Lorelai's home to ask permission to propose to Rory and take her with him. Lorelai, shocked, gives no answer.