Lorelai accepts Max's wedding proposal. Rory and her grandfather get into a fight when he expresses his disapproval of Dean.
Lorelai finally tells her mother that she's getting married but Emily shows no interest in the news. Meanwhile, Rory participates in a house-building project to beef up her college application.
The girls throw a bachelorette party for Lorelai who starts to have serious second thoughts about getting married.
After calling off her wedding, Lorelai decides she needs a road trip. Mother and daughter start driving with no destination in mind. When they discover they're close to Boston, the girls visit Harvard, where Rory gets a glimpse of her future and Lorelai gets a glimpse of the past she might have had.
Luke's sister sends her wild teenage son, Jess, to Luke for him to raise. Luke finds his nephew to be more than he can handle, but he ignores Lorelai's advice about raising kids. Rory starts her new school year by trying to make amends with Paris, but Paris doesn't want to let go of her grudge and sticks Rory with interviewing Max.
Rory wants to participate in the debutante ball and Lorelai can't understand why. Her father returns to tell Lorelai that he has moved on with his life, including a new girlfriend. Meanwhile, Emily and Richard are fighting in public and Lorelai cannot figure out what's going on.
Rory tries to join a famous secret sorority at her school to improve her social skills. Lorelai hosts a fashion show fundraiser for the Booster's Club, but discovers that the models are actually the mothers in the club.
Lorelai panics when she learns that The Independence Inn may be sold. She fears that her dream of opening an inn with Sookie may never come true.
Dean becomes jealous and increasingly suspicious when Rory and Tristan are cast as Romeo and Juliet in the school play.
Sookie's detailed historical-themed dinner is derailed when a blizzard keeps the intended diners away, prompting her and Lorelai to invite all their friends to come.
The house is infested with termites, but Lorelai doesn't have the money for repairs and has can't get a home loan. The only way she can get the money is if she accepts her mother as a co-signer for her loan. Rory gets a 1500 on her PSATs, but is worried that her math scores were higher than her verbal. Rory discovers that Lane is a cheerleader.
Lorelai's newly retired father is driving her mother crazy, so she sends him to Stars Hollow. There, Lorelai finally has it out with her Dad over his constant criticism of her life. Paris freaks out over a newspaper award and Rory has to write a story with her.
Jess outbids Dean for a fundraiser picnic lunch. Meanwhile, Miss Patty is trying to find a man for Lorelai. The ones she chooses end up in a bidding war over Lorelai's basket and she convinces Luke to save her. Jackson and Suki argue over taking the next step and living together. Henry gets tired of waiting for Lane to figure out a way to get around her mother.
Christopher brings his new girlfriend, Sherry, to Stars Hollow. Emily is furious that Lorelai has missed her chance to get together with Christopher.
Rory loses the bracelet that Dean made for her. but when Lorelai catches Dean in Rory's room, she accuses him of stealing it. Meanwhile, Luke buys the building where he lives so that he can expand his living space.
When Emily and Lorelai go to a spa together to relax, Emily loosens up and the two begin to bond with one another. Rory's plans to spend the night at home by herself are repeatedly thwarted.
Rory and Lorelai help Luke out in the diner when he becomes bogged down with funeral arrangements for his dead uncle.
Rory works on a business project for school with Richard, which inspires him to come out of retirement. Meanwhile, Lorelai creates problems for Michel, whose mother is town for a visit.
Rory helps Jess study when he's at risk of flunking out of school. But on the way to their first study session, Jess crashes Rory's car and Rory ends up in the hospital. Lorelai blames Luke and lashes out at him.
Rory is angry that everyone blames Jess for the accident. Meanwhile, a New Yorker moves to town and opens a music store. Lane persuades the owner to allow her to rock out on the drums.
Rory misses Lorelai's graduation day when she sneaks off to New York to visit Jess.
Lorelai spends a romantic night with Rory's father the night before Sookie's wedding. Meanwhile, Rory is reunited with Jess. She's so surprised to see him that she gives him an unintended passionate kiss.