Episodes
Episode 301 "Those Lazy-Hazy-Crazy Days"Lorelai has a strange dream in which she is pregnant with Luke's twins, which Rory interprets as either: Lorelai subconsciously wants to marry Luke and have his twins or that she's jealous that Sherry's pregnancy has doomed Lorelai's hopes with Christopher. Rory comes back from her internship in Washington, where Paris met and dated a Princeton student. Rory is surprised to see Jess making out with another girl and is instantly jealous, but resolves to appreciate her relationship with Dean. The town hosts a summer festival, including a barbershop quartet who only sings "Those Crazy Hazy Lazy Days of Summer" over and over, much to Lorelai's irritation.
Episode 302 "Haunted Leg"
Lorelai turns down a date with Kirk. Rory and Jess quarrel in Doose's market when he points out that she has no right to be jealous, having not contacted him while she was away. Christopher shows up unannounced at Friday-night dinner, having talked with Emily, but is sent away by all three Gilmore women.
Episode 303 "Application Anxiety"
Rory is scared that she may not get in to Harvard after a panel of admissions consultants visits Chilton and emphasizes the competitive process. Rory and Dean start talking about what would happen when Rory leaves for college. Lane joins a rock band, and Taylor wins the town's backing of his plans to open an old-fashioned soda shop.
Episode 304 "One's Got Class and the Other One Dyes"
Lorelai and Luke are invited to speak about success at Stars Hollow High, but the kids just want to hear about Lorelai's teenage pregnancy and their mothers blame Lorelai. Lane, driven to rebellion, dyes her hair purple but loses her nerve and immediately dyes it back. Rory confronts Jess' new girlfriend, Shane.
Episode 305 "Eight O'Clock at the Oasis"
An irritatingly cheerful new neighbor, partial to board games and kitsch, gives Lorelai detailed instructions for watering his lawn and violets during his business trip; when Rory takes over the watering, however, disaster strikes. Lorelai meets a guy at an auction Emily organized, but their subsequent date does not go well.
Episode 306 "Take the Deviled Eggs..."
Rory and Lorelai attend Sherry's baby shower. Lorelai is jealous because Sherry seems to be living the life she was unable to have with Christopher. Sherry gives Lorelai and Rory left-over deviled eggs from the party, which they proceed to throw at Jess's new car.
Episode 307 "They Shoot Gilmores, Don't They?"
Lorelai and Rory compete in the annual Charity Stars Hollow 24-hour dance marathon which Kirk has won 4 times in a row. Jackson and Sookie fight over his hopes for four children in four years. Jamie visits Paris at school during his break. Dean finally announces (to the entire dance hall) that Rory likes Jess. Dean breaks up with Rory for good causing Rory and Lorelai to once again lose to Kirk.
Episode 308 "Let the Games Begin"
Richard, Emily, Lorelai and Rory take a road trip to Yale where Richard tricks Rory into an interview. Rory and Jess begin dating. Kirk's prize from the Marathon goes missing yet again. At bedtime, the Gilmore girls each secretly read promotional material from Yale.
Episode 309 "A Deep-Fried Korean Thanksgiving"
Thanksgiving dinner with the Kims. Thanksgiving dinner with Sookie. Thanksgiving dinner at Luke's. Thanksgiving dinner with the grandparents, where Rory lets slip that she has applied to Yale as well as Harvard. Cat Kirk drives Human Kirk from his home. Lane gets a kiss.
Episode 310 "That'll Do, Pig"
Paris has a boyfriend, and is not herself. Lorelai gives Emily tips on coping with Richard's mother, Trix. Rory begins to ease up around Dean; she and Jess begin to make out publicly. Jess refuses to attend the Winter Carnival, but when Dean asks Rory to join him and his little sister Clara, Jess becomes jealous and decides to escort Rory after all.
Episode 311 "I Solemnly Swear"
Francie tricks Paris into believing that Rory is plotting against her in the Student Council. Lorelai and Sookie attend a lecture on running an inn; it's a total waste, but Sookie meets an old friend Joe, and sparks fly between Lorelai and Joe's business partner Alex. Emily, sued by a fired servant, presses Lorelai to give a deposition, and is outraged at the result.
Episode 312 "Lorelai Out of Water"
Alex invites Lorelai on a fishing trip, so Luke teaches her how to fish without embarrassing herself. Luke also meets Taylor's attractive lawyer, Nicole. Paris escalates her one-sided feud with Rory, and both are reprimanded by the headmaster. Lane is thrilled that her mother said maybe to her request of going to the Prom, that is, until her mother picks out her date.
Episode 313 "Dear Emily and Richard"
Rory receives an invitation to Sherry's C-section. Sherry goes into labor early, and Rory is the only one present. Lorelai reminisces about her own pregnancy and, realizing anew what her mother suffered, makes a reconciliatory gesture toward Emily.
Episode 314 "Swan Song"
Jess comes to Friday night dinner with a black eye, and Rory accuses him of having a fight with Dean, which he denies. Later, Jess admits to Luke that he was attacked by a swan. Rory stays the night at her grandparents' house. Emily yells at Lorelai for letting Rory go out with Jess. Rory later tells Lorelai that she might have sex with Jess soon. Zack and Brian guess that Lane and Dave are hiding a secret, but think that the secret is their religious faith.
Episode 315 "Face-Off"
When Jess does not call, Rory goes to a hockey game and sees Dean with his new girlfriend, Lindsay. Emily gets revenge for Trix's slights when she finds her making out with a man in a jogging suit. Lane and Dave convince her male friend Young Chui to become Lane's fake boyfriend. Rory leaves an angry message for Jess, but after discovering that he was out preparing a surprise for her, she asks him to delete it without listening.
Episode 316 "The Big One"
On the eve of presenting joint speeches over C-SPAN for the school's bicentennial, Paris has a heart-to-heart with Rory, confiding that she finally had sex with her boyfriend and getting Rory to admit she is still a virgin (to an eavesdropping Lorelai's relief). The next day, Paris has a meltdown on live TV, announcing her rejection by Harvard as judgment upon her premarital sex and predicting the virginal Rory will be accepted. Lorelai runs into Max and sparks fly. Sookie discovers she is pregnant. Rory arrives home to find she has been accepted to every school.
Episode 317 "A Tale of Poes and Fire"
The Independence Inn catches fire during a meeting of the Poe Society, so guests move into Lorelai's house, and she spends the night with Luke and Jess, where she tells Luke about her strange dream of months before. Lane discovers Young Chui may never initiate the break up that would free her to date Dave. Rory must choose among Harvard, Princeton, and Yale, but is torn when her pro-con lists point away from the school whose banners cover her wall and toward the school to which Lorelai had opposed her applying.
Episode 318 "Happy Birthday, Baby"
Rory plans Lorelai's big birthday blowout, including a town-sized pizza. Richard gives Lorelai the $75,000 payout from an investment he had made at her birth. Lorelai, in turn, writes a check to her mother to repay the loan for Chilton and end the Friday dinner agreement, then is shocked when her mother is angry at being repaid. Luke's adventures in parenting also go badly when he cannot convince Jess to prioritize school, then scares off Nicole's parents by raving about the situation.
Episode 319 "Keg! Max!"
Jess learns he doesn't get to graduate. Rory, Jess, Dean and Lindsay attend a party where Lane's band is playing. A drunken Lane calls her mother and admits all her deceptions as she despairs of ever having the relationship she wants. Jess makes a pass at Rory after she seeks him out to find why he is acting strangely, then pushes her away when she does not respond as he hoped. She leaves the room crying, which Dean sees, leading him to start a fight with Jess and destroy their host's home. Lorelai, meanwhile, invites Luke and Nicole to stay at the inn, then is distressed by a close look at their coziness.
Episode 320 "Say Goodnight, Gracie"
Jess's father appears, meets Jess, then vanishes after Luke warns him off. Dean and Lindsay get engaged. Fran dies, meaning Lorelai and Sookie may have a chance to buy the Dragonfly. Mrs. Kim agrees to let Dave take Lane to the prom, but only after a mysterious quote that he cannot find anywhere in the Bible. After days of mutual avoidance with Jess, Rory finally tells Lorelai what happened at the party. Jess fights with Luke over how they will handle his failure to graduate, then leaves for California in search of his father.
Episode 321 "Here Comes the Son"
Jess goes to live with his dad in Venice Beach (in a backdoor pilot for a show that was to star the Jess character). Rory stresses over graduation, while Lorelai ponders how to break the news that Jess has left for good.
Episode 322 "Those Are Strings, Pinocchio"
Rory graduates from Chilton. With the Independence Inn set to close, a newly unemployed Lorelai plans to use her inn-buying funds to pay for Yale, until Rory goes behind her back to make a new deal with her grandparents. Lorelai and Sookie buy the Dragonfly. The Gilmore Girls get ready for their European adventure, and Luke, prompted by a conversation with Lorelai, decides to commit to a cruise with Nicole. Rory breaks up with Jess.