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There is no Next Episode of Gilmore Girls planned.
After Rory is accepted at Chilton, an extremely prestigious and expensive prep school, Lorelai's difficulty in raising the tuition money forces her to ask her wealthy parents, from whom she is estranged, for a loan. The elder Gilmores happily loan their daughter the money in exchange for an end to the estrangement and a family dinner every Friday night. In her last week at Stars Hollow High School, Rory meets a very cute new transfer student named Dean, which gives her second thoughts about attending Chilton. When Lorelai discovers that her ambivalence about Chilton centers on a boy, they argue about her future, but after the first Friday night family dinner at her grandparents' house, Rory makes up with her mother and decides to go to Chilton after all when she realizes the sacrifice her mother has made in agreeing to end the estrangement with her grandparents.
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.
When Rory announces at Friday night dinner that she has to pick a team sport to play at Chilton, Emily insists that Richard take Rory to the club and teach her golf. Although Rory tees off to a rocky start, she soon gets into the swing of things and has a great time walking and talking with Richard. Later, Lorelai's mixed feelings as Rory tells her how much she enjoyed being with Richard at the club provokes her into an intensely stupid argument with Rory, which is soon patched up when Lorelai realizes that she's not losing Rory to her parents. At the Inn, Lorelai has her hands full overseeing all the preparations for an ornate double wedding ceremony and contending with a pair of spoiled and quarrelsome twin brides, their exhausted mother, their twin grooms, Michel, and the rest of her staff.
Rory receives the first "D" of her life, pushing her to study like crazy for the upcoming exam. She and Lorelai stay up all hours reviewing every detail about Shakespeare, only to over-sleep and Rory misses the big test. Rory has a meltdown, telling off both Tristan and Paris in the process. Meanwhile, Lorelai meets Mr. Medina at the parent-teacher meeting and tells off the headmaster after Rory's meltdown.
When both a distant family member and a neighbor's cat die, Lorelai has to decide which wake to attend. Max and Lorelai get their feelings for each other out on the table, but what will Rory think of this? Meanwhile, Lorelai and Sookie attend a Chilton bake sale; and Rory and Dean's budding relationship takes one step forward.
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.
Dean gives Rory her first kiss; fearful of her mother's disapproval, Rory decides not to tell Lorelai for a little while; Lorelai gets stressed when she hears about the kiss from Mrs. Kim instead of Rory; Rory freaks out at first when Lorelai invites Dean over to watch videos and eat junk food, but ends up having a good time after all.
The first snowfall prompts Lorelai and Max's first date. Lane is upset with Rory for being distracted with Chilton, and Dean. Rory spends time with her grandparents, and introduces them to frozen pizza. Meanwhile, Luke mocks and refuses to take part in the annual re-enactment of the Battle of Stars Hollow.
Chilton hosts a dance which Rory and Dean attend, confirming that they are "boyfriend-girlfriend". Emily sleeps over at Lorelai's the night of the dance to take care of Lorelai's injured back and to see Rory off. Rory and Dean fall asleep accidentally, causing Rory to arrive home at 5 a.m., which pushes Emily to think they had sex. Thus erupts another blow-up between Lorelai and her mother.
Things are still chilly between Rory and Lorelai; Lane gives Rory advice about the right Christmas gift for Dean; Emily and Lorelai have a tiff about Christmas dinner, leaving Rory to go by herself; Dean and Lorelai patch things up; Luke makes a lonely Lorelai a Santa burger; Richard collapses and is rushed to the hospital; Luke gives a car-less Lorelai a ride to the hospital; relieved that Richard's collapse was only a bout of angina, the Gilmores settle their differences.
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.
After Lorelai encourages Sookie to ask out Jackson, she finds herself on the double date from hell with Jackson's cousin, Rune, which makes Luke jealous enough to finally work up the courage to ask Lorelai out. Meanwhile, Rory and Lane get into trouble when they double date with Dean and his friend Todd without telling their moms.
Lorelai, Sookie, Rory, and Lane plan to attend The Bangles concert, but when Lane's mother finds the truth, she bans her from going. Lorelai and Sookie offer up the three tickets so Rory can take Madeline, Louise, and Paris which backfires when Madeline and Louise take off with two mysterious boys for a party.
An evening of "The Donna Reed Show" reruns infects Dean and both Gilmore Girls -- Dean expresses a longing for the type of family represented by the show, Lorelai helps Luke spruce up the diner with a fresh paint job and new curtains, and Rory dresses up like Donna and fixes a 1950s style dinner for Dean while petsitting Babette's new kitten; when the baby chick that's the subject of Rory's midterm project gets loose in the house, Lorelai frantically calls Luke to help her search the house; both Sookie and Emily force Lorelai to confront her feelings for Luke; Christopher roars into town on his motorcycle, and agrees to stay at Lorelai's and Rory's during his visit.
Wanting to play a greater role in Rory's life, Christopher settles in for his visit and lets Rory give him the grand tour of Stars Hollow. When his parents arrive in Hartford for a visit, Emily invites everyone to Friday night dinner, which turns out to be an unqualified disaster after Richard nearly comes to blows with Christopher's father over critical comments about Lorelai. In the aftermath of the ruined dinner party, Richard retreats to his study to calm down, Emily makes a plate for Rory in the kitchen and reassures her how much she is loved and regarded, and Christopher finds Lorelai on the balcony of her old bedroom and comforts her by repeating a little romantic history. The next morning, Lorelai awakens with a start, horrified that she forgot to help Luke paint the diner after dinner on Friday night. Grabbing a jacket, she races to the diner still clad in her pajamas, and begs Luke's forgiveness. He shrugs it off at first, but appears somewhat wounded when he realizes that Lorelai was with Christopher the night before. When Lorelai returns to the house, Christopher asks her to marry him and she regretfully turns him down, claiming he's not ready for the responsibility of a family quite yet. Christopher returns to California with the promise of doing a better job of staying in touch. The next morning, Lorelai surprises Luke by having the diner completely repainted when he arrives to open up for the day.
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 her. As they sit in the car, Dean professes his love, but Rory is unsure how to respond.
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.
Rachel finds an abandoned inn that Lorelai and Sookie fall in love with; Lorelai and Rachel spend the afternoon getting to know each other and Rachel asks Lorelai to put in a good word for her with Luke; as Rory takes Emily on a tour of Stars Hollow, Emily hits it off with Mrs. Kim and Michel, but becomes distraught when she sees Lorelai and Rory's first home; at Sookie's urging, Lorelai gives Jackson's cousin, Rune, a job at the Inn.
Lorelai helps Luke shop for a birthday present for Rachel and goes wild outfitting him with a new wardrobe; overwhelmed by sadness at her breakup with Dean, Rory is distressed to discover that Lane and Dean have become science project partners, and incensed to find out from Max that Lorelai has neglected to mention that they are dating again, so she argues with Lorelai and then takes off for Hartford to spend the night at her grandparents' house without telling her mother; when an angry Lorelai confronts Dean and discovers the truth about his breakup with Rory, she fears that she has taught Rory not to commit to a relationship.
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.