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.

Lorelai oversleeps on Rory's first day at Chilton to the dismay of her daughter. Rory's day goes downhill from there 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. At the Inn, Lorelai has her hands full overseeing all the preparations for an ornate double wedding ceremony.

Max Medina gives Rory the first "D" of her life on an English paper. Lorelai spends the week helping Rory study, but things don't go as planned, ending in Rory having a meltdown, finally giving Paris and Tristan the chewing out they so richly deserve.

During their weekly dinner at Emily's, Lorelai learns of her cousin's funeral. The next day Rory reminds Lorelai of the Chilton bake sale where Lorelai accepts to meet Max Medina, Rory's teacher, for coffee. Rory's friendship with Dean takes a new turn.

It's Rory's birthday, and her grandmother and mother each plan a party representative of their respective styles.

Dean gives Rory her first kiss: fearful of her mother's disapproval, Rory decides not to tell her her yet. However Lorelai hears about the kiss and invites Dean over to watch videos and eat junk food.

The first snow of the season falls heavily, stranding Rory at Emily and Richard's house. Luke is obsessing about the silliness of the re-enactment of the Battle of Stars Hollow in the town square. Lorelai is enjoying a walk alone in the snow when she comes upon Max. Lane decides to pay a visit to Rory.

During dinner at her mother's, Lorelai finds out that not only is there a formal dance at Chilton, but that Rory doesn't want to go. Eventually Lane prods Rory into asking Dean to go, and she nervously does so, creating tensions between Emily and Lorelai.

Things are still chilly between Rory and Lorelai. Lane gives Rory advice about the right Christmas gift for Dean. The Gilmores are forced to settle their differences as a tragic event bring them closer.

Sookie and Lorelai have a frank talk about relationships. Paris needs to make amends after revealing a parent/teacher affair. Sookie asks Jackson out on a date.

Lorelai finds herself on the double date from hell with Jackson's very odd cousin after offering to help ou Sookie. Meanwhile, Rory and Lane get into trouble when they double date with Dean and his friend Todd without telling their moms.

Lorelai organizes the Stars Hollow Charity Rummage Sale, leading her to learn new informations about Luke's love life. Rory and her friends head to New York for a concert.

An evening of "The Donna Reed Show" reruns infects Dean and both Gilmore Girls. Lorelai helps Luke spruce up the diner with a fresh paint job and new curtains. Sookie and Emily force Lorelai to confront her feelings for Luke.

Wanting to play a greater role in Rory's life, Christopher settles in for his visit. When his parents arrive in Hartford for a visit, Emily invites everyone to Friday night dinner, which turns out to be an unqualified disaster.

Luke's ex-girlfriend Rachel arrives in Stars Hollow unexpectedly. 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.

Rory decides to engage in a flurry of activity to avoid thinking about Dean, despite Lorelai's advice to wallow. 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.

Paris is outraged when she discovers that Tristan asked her for a date at Rory's urging. Emily opposes Trix's offer to set up a trust fund for Rory, afraid she'll never see Lorelai again.

Rachel finds an abandoned inn that Lorelai and Sookie fall in love with. 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. Meanwhile 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.

Rachel makes an important decision after she becomes convinced that despite his protests, Luke is in love with Lorelai. Rory finally manages to talk to Dean about her feelings.