Lorelai accepts Max's proposal, but when Emily hears about the upcoming wedding from Sookie, she is hurt and angry that Lorelai didn't bother to tell her. Meanwhile, Rory brings Dean to dinner at her grandparents' house and Richard's obvious disapproval of Dean leads to the first fight between Rory and her grandfather.
Lorelai avoids telling her parents about her engagement to Max, while Rory urges her to spill. But due to a call from Sookie asking them to come to a surprise wedding shower for the happy couple, they already know, and are appalled that Lorelai didn't tell them and so they give her the cold shoulder. Meanwhile, Rory and Dean are having trouble in paradise due to the fact that Rory suddenly becomes obsessed with finding enough extracurricular activities that will set her apart from the hundreds of other Harvard applicants.
The Gilmore Girls' road trip takes them to a most unusual bed and breakfast and more importantly to tour Harvard and Rory's possible future. Meanwhile Lorelai decides to move forward with her dream of opening an inn.
Rory surprises everyone by agreeing to Emily's request that she make her debut at a Debutante Ball, and when Lorelai asks Rory's dad Christopher to present his daughter to society, she finds herself attracted to the new, more responsible man he has become.
Chilton's headmaster Charleston thinks Rory isn't properly socializing and when Lorelai disagrees he tells her Rory may be taking after her mom. Rory's attempt to reach out gets her involved with a sorority while Lorilais becomes a booster.
Lorelai and Sookie have the first fight of their long friendship when, upon hearing that the Independence Inn may be sold, Lorelai panics and decides that their shared dream of opening an inn together is doomed to failure.
When Rory and Tristan are cast as Romeo and Juliet in a school play, a jealous Dean insists on attending every rehearsal, forcing Rory to beg Tristan not to tell Dean about the time they shared a kiss, while Lorelai has to put up with Luke's teasing after she dates a much younger guy.
While Rory struggles to keep the budding rivalry between Dean and Jess under control, Lorelai invites most of the citizens of Stars Hollow to an elaborate feast complete with Elizabethan costumes and horse-drawn sleigh rides, during which Richard announces to Emily that he has retired.
Newly retired Richard is driving Emily crazy, so Lorelai is coerced into taking her father for a day in Stars Hollow, where he proceeds to drive both Lorelai and Rory batty while criticizing every aspect of their lives and refusing to let Rory accept the car that Dean has built for her.
During the annual Stars Hollow charity picnic basket auction, both Lorelai and Rory's baskets have more competition then they both anticipated. Meanwhile Jackson refuses to bid on Sookie's basket leading them to work on their communication. Rory and Lorelai have their own communication problems but work it out after Emily sides with Lorelai's initial reaction to Jess worming his way into Rory's life.
Christopher and his girlfriend Sherry visit Stars Hollow leading Sherry to push for a Friday night out alone with Rory to bond. So Lorelai takes Christopher to a tumultuous Friday night dinner at her parents. Lorelai, thinking she missed out on a life with Christopher, confesses her self-realization.
Rory panics when she suddenly realizes that she lost the bracelet Dean made for her, and when a suspicious Lorelai catches Jess in Rory's room, she accuses him of stealing the bracelet. Meanwhile, Luke goes a little stir-crazy after living with Jess in the tiny apartment over the diner, and he impulsively buys the building so he can expand.
Lorelai and Emily spend a weekend at a health spa, but they sneak out for some real food at a local restaurant where Emily dances with a distinguished stranger, then blames Lorelai for her feelings of guilt. Back at home, Rory looks forward to a rare evening alone, but when Paris, Jess and Dean all drop by to keep her company, the sparks fly.
Lorelai and Rory help out at the diner while Luke is left to plan his unpleasant uncle's funeral, which causes him to reflect on his own existence. Meanwhile, Emily lends a hand planning Sookies wedding and the skies the limit.
After helping Rory out with her business project for the annual Chilton Business Fair, Richard realizes retirement isn't for him. Meanwhile Dean, for good reason, is feeling insecure about Rory. Michel's mother visits and their once great relationship is over after Lorelai interferes.
Luke asks Rory to tutor Jess who is close to failing, but Jess uses it to get closer to Rory and when they get into a car accident, Lorelai takes it out on Luke for taking Jess in to begin with. Lorelai takes over the movie selection for the town square movie night, but in the end realizes why Taylor chooses the same movie every year and Kirk uses the night to show of his work.
Lorelai helps her dad open his new office and gets the cold shoulder when she tells him she has a job already. Rory tries to let everyone know Jess wasn't the only one at fault for the accident and with a new music store in town, Lane discovers her new love.
After doing her best to avoid Luke, Lorelai can't avoid the inevitable, but Luke isn't ready to patch things up yet. Rory invites her grandparents to her mom's graduation, but misses it herself after cutting school to meet Jess in New York.
It's Sookie's wedding day and Jackson is wearing a kilt. Jess and Rory happen to see each other before the wedding, which Rory and Lorelai are part of. Chris has to leave because his girlfriend calls with some news.