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When Rory gets accepted to a fancy prep school, Lorelai is forced to humble herself and ask her mother for help in paying the tuition.

A T-shirt, shorts and cowboy boots-clad Lorelai accompanies Rory on her first day at school, drawing disapproving stares from the other mothers and Lorelai's own mother, Emily.

When Richard and Rory form an instant bond during a day of golf, Lorelai feels left out and finds it difficult to observe Rory's emotional connection with Emily and Richard.

Rory has trouble getting good grades at her new school. Lorelai becomes interested in Rory's handsome teacher.

Lorelai forgets to tell Rory that she has a date with Rory's teacher Max. Rory has a new crush.

Emily plans a formal birthday party for Rory, who reveals that she would not like to have a formal party. However, Lorelai's party for Rory is a success.

Rory decides not to tell her mother that she and Dean have kissed. Lorelai takes the liberty of inviting Dean over, and Rory is embarrassed by her mother's actions.

Lorelai shares a wonderful day with Max while Rory is snowed in at her grandparents' home. Lane misses Rory and comes to visit.

Rory turns down two boys' offers to take her to a school dance and instead chooses to go with Dean. Dean gets into conflict with the two jealous boys who were rejected by Rory.

Richard collapses. Dean assures Lorelai that nothing improper happened on the night he and Rory fell asleep together. Lorelai and Luke seem to be more attracted to each other.

Paris exposes the relationship between Lorelai and Rory's teacher, Max. When Rory confronts Paris, she admits that she wanted to deflect attention away from her parents' divorce.

Lorelai finds herself on a hellish double date with Sookie, Jackson, and Jackson's very odd cousin. Meanwhile, Rory double dates with Dean, Lane, and Dean's friend.

Trouble occurs when Rory brings her friends to a concert by The Bangles.

Rory and Dean disagree about women's roles after watching 'The Donna Reed Show.'

Rory's father, Christopher, returns, causing tension in Emily and Richard's house—and forcing Lorelai to make a big decision about her family's future.

Dean and Rory share a special evening as the town celebrates its romantic history.

Dean ends his and Rory's relationship on their anniversary. When Rory's classmate Tristin kisses her, she admits to herself how confused she is. Meanwhile, Lorelai visits Max.

Emily becomes worried when Lorelai's grandmother offers Lorelai a trust fund for Rory's education. Meanwhile, Rory feels uncomfortable near Tristin after their kiss.

Aghast to finally see the conditions in which Lorelai reared Rory instead of living with Richard and her, Emily tries to create the perfect bedroom for Rory in her house.

Upset over Dean, Rory becomes angry with Lorelai, who didn't tell her that she's dating Max again. Dean tells Lorelai that he left Rory because she couldn't say 'I love you.'

Rory finally tells Dean that she loves him. Rachel senses that Lorelai and Luke are attracted and leaves town rather than pursue Luke anymore. Max proposes marriage to Lorelai.