Episode 1 : Pilot
When Rory gets accepted to a fancy prep school, Lorelia is forced to humble herself and ask her mother for help in paying the tuition.
Episode 2 : The Lorelais' First Day At Chilton
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 from Lorelai's own mother, Emily. Lorelai and Emily argue over money for Rory.
Episode 3 : Kill Me Now
When Richard and Rory form an instant bond during a wonderful day of golf, Lorelai feels left out and finds it difficult to observe Rory's emotional connection with Emily and Richard, knowing that she herself lacks the same intimacy.
Episode 4 : The Deer Hunters
Rory has trouble getting good grades at her new school. Lorelai becomes interested in Rory's handsome teacher.
Episode 5 : Cinnamon's Wake
Lorelai forgets to tell Rory that she has a date with Rory's teacher Max. Rory has a new crush.
Episode 6 : Rory's Birthday Parties
Rory gets upset at Emily, who plans a formal birthday party for her but feels that Rory is being ungrateful when Rory reveals that she would not like to have a formal birthday party. However, Lorelai's party for Rory is a success.
Episode 7 : Kiss and Tell
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.
Episode 8 : Love and War and Snow
Lorelai shares a wonderful day with Max while Rory is snowed in at her grandparents' home. Lane misses Rory and comes to visit.
Episode 9 : Rory's Dance
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.
Episode 10 : Forgiveness and Stuff
Richard collapses at the Gilmore's Christmas party. 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.
Episode 11 : Paris Is Burning
Paris exposes the relationship between Lorelai and Rory's teacher, Max, causing a scandal. Lorelai and Max sadly part.
Episode 12 : Double Date
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. They keep their plans secret because Lane's protective mother would not approve.
Episode 13 : Concert Interruptus
Trouble occurs when Rory brings her friends to a concert by The Bangles.
Episode 14 : That Damn Donna Reed
Rory and Dean disagree about women's roles after watching "The Donna Reed Show."
Episode 15 : Christopher Returns
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.
Episode 16 : Star-Crossed Lovers and Other Strangers
Dean and Rory share a special evening as the town celebrates its romantic history.
Episode 17 : The Breakup, Pt. 2
Dean ends his and Rory's relationship on the night of their third anniversary. Refusing to indulge in self-pity, Rory attends a party and finds her classmate Tristin, who just lost his girlfriend. When Tristin kisses Rory, she finally admits to herself how confused and miserable she is. Meanwhile, Lorelai visits Max, and the two can't resist making love.
Episode 18 : The Third Lorelai
Emily becomes worried when Lorelai's grandmother offers Lorelai a trust fund for Rory's education. If Lorelai accepts the trust fund, Emily fears she will lose contact with Lorelai and Rory once they are not financially dependent on her. Meanwhile, Rory feels uncomfortable near Tristin after their kiss. She tries to pair Tristin with Paris, not realizing that she herself is the one whom Tristin is interested in.
Episode 19 : Emily In Wonderland
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.
Episode 20 : P.S. I Lo...
Still upset over Dean, Rory becomes angry with Lorelai, who didn't tell her that she is dating Max again. Dean tells Lorelai that he left Rory because she couldn't say "I love you," and Lorelai urges Rory to express her emotions more freely.
Episode 21 : Love, Daisies and Troubadours
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 also senses the attraction, which Lorelai denies. When Max proposes marriage to Lorelai, she is caught off guard and rebuffs him saying he should have done it the "right" way with 1,000 daisies and a white horse. The next day, Lorelai arrives at the inn to find it full of daisies. Again, Max proposes marriage, and Lorelai considers her response...