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Lorelai accepts Max Medina's marriage proposal, but when Emily hears about the upcoming wedding from Sookie, the elder woman is hurt and angry that Lorelai didn't bother to tell her. Soon, the whole town is busy making wedding arrangements, but her mother's attitude dampens the bridal bliss for Lorelai. 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 accepts Max Medina's marriage proposal, but when Emily hears about the upcoming wedding from Sookie, the elder woman is hurt and angry that Lorelai didn't bother to tell her. Soon, the whole town is busy making wedding arrangements, but her mother's attitude dampens the bridal bliss for Lorelai. 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.

During a wild bachelorette party hosted by Sookie, Lorelai makes an impulsive telephone call to Rory's father, Christopher, and sadly realizes that Max is not the man for her.

With the wedding canceled, Lorelai is eager to escape the sympathies of everyone in Stars Hollow, so she and Rory take off on a road trip that ultimately leads to Harvard University. While Rory confronts her dreams of college life, Lorelai ponders what might have been.

Lorelai's well-intentioned advice doesn't dissuade Luke from reluctantly agreeing to care for his wild 17-year-old nephew Jess. Rory finds herself attracted to Jess, the town's newest resident.

Emily requests that Rory partake in a debutante ball. To everyone's surprise, Rory agrees. After asking Rory's father, Christopher, to present Rory to society, Lorelai finds herself attracted to the new, more responsible man he has become.

Rory is told by her guidance counselor that she is perceived as a loner, and her subsequent, reluctant efforts to socialize put her in the most popular clique at Chilton. Meanwhile, the chancellor of Chilton recommends that Lorelai participate more in school activities, so she volunteers the Inn as a venue for a Chilton fund-raising fashion show. She is later horrified to find herself modeling matching outfits with her mother, Emily.

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 fail.

When Rory and her classmate 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 she and Tristan kissed. Meanwhile, Lorelai has to endure 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 the event, Richard stuns Emily by revealing that he has retired.

Lorelai is concerned because she can't afford to repair her home's extensive termite damage. She becomes angry when Rory tells Emily about the problem, and Emily again offers Lorelai a loan. Meanwhile, Rory is confused when Lane joins the cheerleading squad, despite having always mocked it.

Newly retired Richard is making Emily crazy, so Lorelai agrees to take her father for a day in Stars Hollow, where he proceeds to annoy both Lorelai and Rory. Richard criticizes every aspect of their lives and refuses to let Rory accept a car that Dean built for her.

The annual Stars Hollow Picnic Basket Auction causes romantic complications when Jess outbids Dean to win a picnic lunch date with Rory. A fight ensues between Rory and Dean, and she has an even bigger argument with Lorelai over Rory's socializing with Jess.

Lorelai and Rory are stunned when Rory's father, Christopher, brings his new girlfriend, Sherry, to Stars Hollow. Sherry makes it obvious that she wants to build a meaningful relationship with Rory. Meanwhile, when Emily learns about Sherry, she becomes furious with Lorelai for failing to win Christopher back.

Rory panics when she realizes that she has lost the bracelet that Dean made for her. When the suspicious Lorelai witnesses Jess in Rory's room, she accuses him of stealing. Meanwhile, exasperated with sharing his cramped apartment over the diner with Jess, Luke impulsively buys the entire building in order to expand.

Lorelai and Emily are at a health spa for the weekend, but they sneak out for some unauthorized food at a local restaurant. There, Emily dances with a distinguished stranger, Chad, and blames Lorelai for her feelings of guilt. At home, Rory looks forward to a rare evening alone, but problems occur when Paris, Jess and Dean all come to the house unexpectedly.

Luke is overwhelmed by the funeral arrangements he must make for his deceased Uncle Louie, who was Stars Hollow's most disliked citizen, so Lorelai and Rory work at Luke's diner--without much help from Jess. Meanwhile, Emily's extravagant suggestions for Sookie's upcoming wedding to Jackson make everyone crazy.

When Chilton hosts its annual business fair, Rory must create and market a first-aid kit for teenagers, so she asks her newly retired grandfather, Richard, for advice. He is so thrilled to work on a business project that he decides to start a second career. Meanwhile, Lorelai causes problems for Michel when his flamboyant mother, Giselle, visits town. And Dean feels miserable when he suspects that Rory is no longer romantically interested in him.

Luke asks Rory for help after he learns that Jess is failing several high school classes. However, during their first study session, Jess convinces Rory to let him drive her car, and he crashes it, breaking Rory's wrist. Lorelai becomes furious at Luke for putting Rory in danger by encouraging Jess to study with her, prompting Luke to put Jess on a bus to New York.

Lorelai volunteers her organizational skills to help Richard establish a consulting business. As Rory gradually realizes that everyone in Stars Hollow blames Jess for the accident that led to her broken wrist, her anger and guilt finally lead to an outburst directed at Emily. Meanwhile, Lane discovers a new desire to become a rock drummer when a former New Yorker named Sophie opens the town's first music store.

As Lorelai frantically prepares for her final examinations in business school, Rory secretly invites townspeople--including Richard and Emily--to Lorelai's graduation ceremony. Christopher gives Lorelai a special gift, and Sookie bakes a cake. Meanwhile, without telling anyone, Rory travels to New York, where Jess has been living since Luke sent him away. Everyone happily gathers for Lorelai's proud moment, but Rory is not there! Her bus is delayed by an accident, and she misses the graduation ceremony. Lorelai is upset until she realizes that Rory truly loves Jess. Rory doesn't believe that she could love anyone but Dean, but she is happy to celebrate Lorelai's graduation with her a little late.

On the eve of Sookie's wedding, Lorelai and Christopher share an intimate night together. However, their discussion of perhaps resuming their relationship ends when Christopher gets an unexpected message from his former girlfriend. Meanwhile, Rory is so happy to see Jess when he returns to Stars Hollow that she surprises him--and herself--by greeting him with a passionate kiss.