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

It's Rory's birthday, and her grandmother and mother each plan a party representative of their respective styles; Emily's elegant party so discomfits Rory that they argue; to make peace, Emily and Richard attend Lorelai's informal bash the next evening.

During dinner at her mother's, Lorelai finds out that not only is there a formal dance at Chilton, but that Rory doesn't want to go. On the way home, Lorelai convinces Rory that she needs to have this experience, and even offers to make Rory a dress. Lane prods Rory into asking Dean to go, and she nervously does. Even though he says he doesn't really like dances, he agrees to go with Rory. When Emily arrives at Lorelai's the night of the dance to see Rory off and take some pictures, she finds that Lorelai has thrown her back out. She decides to stay and to take care of Lorelai,and they manage to get in some nice mother-daughter bonding during the course of the evening. The dance starts off well; Rory's dress is complimented, Dean is admired, and Paris is embarrassed when everyone finds out that her date is her cousin and that he insisted upon being paid to escort Paris. Unfortunately, Tristan baits Dean, and they almost get into a fight before Dean warns him never to come near Rory aga

As Lorelai and Max grow closer, Rory begins to get attached to the idea of Max in their lives, which freaks Lorelai out; Sookie and Lorelai have a frank talk about relationships; Lorelai tries to ease out of her relationship with Max during Parent's Day at Chilton, but ends up passionately kissing him in his classroom just as Paris walks by; stung by the details in the newspapers about her parents' messy divorce, Paris tells everyone in the lunchroom about Max and Lorelai to deflect gossip away from her and towards Rory; Rory confronts Paris, gets an apology, and offers a sympathetic ear, which is grudgingly accepted; Sookie asks Jackson out on a date and he accepts.

Lorelai organizes the Stars Hollow Charity Rummage Sale and buys a sweatshirt donated by Luke. When she wears it into the diner, he goes ballistic, much to her shock. Sookie tells her later that the sweatshirt belonged to his old girlfriend Rachel, who broke his heart. When Lorelai's curiosity gets the better of her and she demands details from Sookie, Sookie teases her about being jealous of Rachel, which Lorelai denies a little too strongly. Lorelai returns the sweatshirt to Luke, reminding him that it's okay to hold onto some good memories.

Luke's ex-girlfriend Rachel arrives in Stars Hollow unexpectedly, and immediately picks up on the attraction between Luke and Lorelai, which they deny. Rachel decides to stay for awhile, which leaves Luke and Lorelai with mixed feelings. Lorelai and Rory are amazed when Emily agrees to excuse Rory from Friday night dinner so that Rory and Dean can celebrate their three month anniversary. When Lorelai arrives for dinner, she discovers the source of Emily's largesse -- her mother has invited another guest -- a man with whom she secretly hopes to fix Lorelai up. After a painful dinner with one of the world's most boring men, Lorelai attempts to escape through the window of her old bedroom, but is caught in the act by Richard. When he is forced to admit that even he is bored by the man, he uncharacteristically covers for her and lets her make her getaway. Back in Stars Hollow, Dean treats Rory to a wonderfully romantic dinner, and then gives her a present -- a car that he's restoring for h

Rory decides to engage in a flurry of activity to avoid thinking about Dean, despite Lorelai's advice to wallow; Lorelai runs interference as the residents of Stars Hollow reach out to console Rory and Luke attempts to bar Dean from the diner; Rachel pitches in to help Luke out at the diner; Jackson prepares dinner for Sookie, and has a tough time keeping her out of the kitchen; Rory decides to attend Madeline's party and takes Lane along for company; Lorelai decides to visit Max when she realizes how much she misses him; Lane is torn when she meets the perfect guy at the party; Rory attempts to befriend Tristan after he has very public breakup with his girlfriend at the party, and when he apologizes for his past bad behavior towards her and kisses her, she bursts into tears; at home, Rory sobs to Lorelai that she's ready to wallow now.

Emily becomes unhinged at the prospect of a visit from Richard's mother Trix; Paris is outraged when she discovers that Tristan asked her for a date at Rory's urging; fearing that she'll never see Lorelai again, Emily opposes Trix's offer to set up a trust fund for Rory.

Paris wreaks her revenge after Tristan lies about going to a concert with Rory; Rachel leaves Stars Hollow after she becomes convinced that despite his protests, Luke is in love with Lorelai; Rory's defense of the Stars Hollow troubadour during a town meeting brings her back together with Dean, enabling her to finally say, and mean, the words that he's been longing to hear; Luke and Max meet and engage in a little not-so-friendly rivalry as Max begins to suspect, despite her protests, that Lorelai and Luke were once an item; Max proposes to Lorelai with a thousand yellow daisies.

Lorelai receives a late wedding present without a card attached, and insists that it be returned. Sookie sees to what great lengths Lorelai is going to find out who sent it, and tells Lorelai to move forward in life to get some closure on her relationship with Max. Lorelai takes her advice and accepts a dinner date with Paul, one of the other students in her business class. The date goes well, but they decide to remain friends because they don't have very much in common. When Paul appears at Luke's the following Saturday with his parents in tow, Lorelai gets ribbed by everyone in town because he's so young. Luke is uncharacteristically quiet, which Lorelai can't figure out until Sookie explains that he's had a crush on Lorelai forever. Lorelai goes to him to let him know that he'll always be a very important part of her life, and Luke brightens up again.

Rory, Paris, Madeline and Louise are assigned to present the death scene from ""Romeo and Juliet"" as part of ther class participation