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.

During their weekly dinner at Emily's, Lorelai learns of her cousin Claudia's funeral, but as she didn't know the woman, she doesn't want to go. The next day Rory reminds Lorelai of the Chilton bake sale, and on their way out they meet their neighbors Babette and Morey out walking their cat Cinnamon. Dean surprises Rory at the bus stop and rides with her for a little bit, telling her ""Goodbye, Lorelai Gilmore"" as he leaves. At the Chilton bake sale, Lorelai sees Max Medina and is cold to him, but after he tells her that he wants to help Rory and be friends, she agrees to meet him for coffee. Rory ""accidentally"" runs into Dean at the market, and is teased by Miss Patty for it. Lorelai meets with Max, who says that they should date. Lorelai thinks it's a bad idea. Max proceeds to tell her that they are attracted to each other, and after a sad story about seizing the day, Lorelai agrees to dinner. Max leaves her with ""Goodbye, Lorelai Gilmore,"" leaving her just as flustered as Rory was wh

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.

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.

Lorelai, Sookie, Emily, Michel, and Rory go to a drag club for Lorelai's bachelorette party; Emily regales the group with stories about the week before her wedding, some of which give Lorelai pause about her own feelings about marriage; when everyone else leaves to call their sweeties, Lorelai calls Christopher instead of Max; later that evening at home, Lorelai announces to Rory that she's calling the wedding off because she's realized that Max isn't the one for her; mother and daughter decide to take a road trip to avoid the sympathies of all of Stars Hollow.

A blizzard prevents a group from attending the historical dinner that Sookie has painstakingly prepared at their request, so she and Lorelai decide to invite all their friends in Stars Hollow to enjoy the feast at the Inn. At Rory's urging, Lorelai also invites Richard and Emily, in an attempt to boost Richard's spirits. During dinner, Emily is hurt and angered when Richard reveals that he has quit his job without consulting her. Jess tries to get between Rory and Dean when Dean is distracted by his little sister.

Sookie's wedding draws near, and both bride and groom are getting frazzled, to say nothing of Michel, who Lorelai has placed in charge of the preparations at the Inn.

Lorelai finally relents and goes into the diner, where she apologizes profusely to Luke, who is polite, but cool and somewhat remote.

Christopher comes to town for the removal of Rory's cast and decides to stay for Sookie's wedding. After he confesses that his relationship with Sherrie is over, he and Lorelai rekindle their relationship, much to the delight of both Rory and Emily. Their reunion is cut short when Sherrie telephones Christopher to tell him she's pregnant, and Christopher returns to Boston, leaving Lorelai devastated.

Paris is running for student body president. She's commissioned Madeline and Louise to poll the student body and is shocked to find that even though she's overwhelmingly considered to be the most competent candidate, she'll probably lose the election because she's also the least liked candidate

Lorelai is determined to win the Stars Hollow Dance Marathon and wrest the trophy from four-time champion Kirk, but has trouble getting a partner until she finally convinces Rory to help her dance her way to victory. Dean sits on the sidelines to cheer his girl on, and is soon joined by Jess and Shane, who spend their time making out while Jess keeps his eye on Rory. Lorelai breaks her heel, and Dean takes her place while Luke plays shoe repairman. On the dance floor, Dean realizes that Rory is attracted to Jess and breaks up with her. Rory tearfully runs off, followed closely by Jess, and Kirk is declared the winner once again.

It's Thanksgiving, and Lorelai and Rory have dinner at four different places: the Kim's, where Lane has managed to get Dave invited and Lorelai is forced to eat tofurkey; Luke's, where Luke and Jess make it a foursome with Lorelai and Rory; Sookie's, where

Jackson and his family have deep-fried the turkey, the lawn and just about everything else; and Emily and Richard's, where,to Lorelai's horror, Rory reveals that she has applied to Yale. Kirk gets a cat, with disastrous results; Dave asks Lane out, and then kisses her; Paris is afraid her difficulty getting into a shelter will impact her acceptance to Harvard; and Dean faces off with Jess and lets him know that it's no more ""Mr. Nice Guy"" for Mr. Forester.

Rory finally learns her mother can't afford to buy the Dragonfly Inn since financial aid for Yale didn't come through. She decides to take matters into her own hands with a quick visit to her grandparents' right before graduation. Luke has second thoughts about a trip with Nicole after something Lorelai tells him. Jess makes silent contact with Rory after she gives her speech at Chilton.

Lorelai and Rory return from their whirlwind tour of Europe; Taylor and Luke have it out over the new soda shop; a very pregnant Sookie updates Lorelai on the latest baby news; Taylor doesn't take it well when Rory declines the privilege of being the Stars Hollow Ice Cream Queen; mother and daughter get caught up in a flurry of activity after Rory realizes that she wrote down the wrong date for freshman orientation, and she only has two days to get ready for Yale, instead of the week she was planning on; Emily is upset when Lorelai misses Friday night dinner and retailates by turning it into a four hour extravaganza, complete with ballroom dancing videos before the souffle course; Lorelai is shocked when Luke finally tells her what happened on his cruise with Nicole.

Lorelai does her best to get Luke to not give up on them after the awful events at the wedding. Luke tells her he needs some time and Lorelai can't take it. Rory asks Logan to hang out with her but is upset that when she gets to his place that there are a lot of people there. She gets a call from Sookie who tells her that Lorelai is in bad shape after Luke told her that he didn't think he could be in this relationship. Rory doesn't have a car, but Logan lets her borrow his car and driver. Taylor has the whole town taking sides for either Luke or Lorelai. After taking care of her mom Rory goes back to Yale to work things out with Logan, making sure he understood that the hanging out didn't just mean hanging out, it meant alone time.

Lorelai refuses to listen to Richard's plan to bribe Rory into resuming school, saying that Rory has to want to go back on her own. Both Rory and Lorelai are saddened by the fact that their estrangement is keeping them apart on Rory's 21st birthday. Emily takes it upon herself to plan a party for her granddaughter when Rory shows no interest in the event. Richard and Emily find out that Rory and Logan have been sleeping together. Lorelai tries to convince Luke to participate in her mad scientist Halloween skit.

When Taylor spends all of the Spring budget on a hay bale maze, it forces Lorelai and Luke to reunite while in the hay bale maze. Rory and Logan come to Stars Hollow for the Spring fair and Rory learns that she was given a job offer for a newspaper. When she evaluates what she truly wants she decides to reject the job offer and wait on an internship at the New York Times.

After getting into a science camp, April tells Luke that she cannot go on the boating trip with him over the summer. Zach is asked to go on tour with another band. A drunk Lorelai serenades Luke at Karaoke night. Logan gets a job in San Francisco, where he then goes to Lorelai's home to ask permission to propose to Rory and take her with him. Lorelai, shocked, gives no answer.

At Rory's graduation party at her grandparent's house, Logan proposes to her. Emily and Richard sing Rory a graduation song. Rory is caught off-guard and says she needs time to think about it. After Rory graduates from Yale, she tells Logan that she can't marry him. Logan tells her it's all or nothing and Rory decides to decline. Logan ends their relationship.

Rory lands her dream job as a political reporter in Ohio. Luke enlists the help of everyone in Stars Hollow to throw her a graduation party in order to say goodbye. Luke's thoughtfulness brings out a long-awaited reaction from Lorelai.