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.
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.
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.
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.
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.
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 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.
Paris exposes the relationship between Lorelai and Rory's teacher, Max, causing a scandal. Lorelai and Max sadly part.
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.
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 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.
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.
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.
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.
When Chilton hosts its annual business fair, Rory must create and market a first-aid kit for teenagers, so she asks her newly retired grandfather, Richard, for advice. He is so thrilled to work on a business project that he decides to start a second career. Meanwhile, Lorelai causes problems for Michel when his flamboyant mother, Giselle (Janet Hubert), visits town. And Dean feels miserable when he suspects that Rory is no longer romantically interested in him.
Luke asks Rory for help after he learns that Jess is failing several high school classes. However, during their first study session, Jess convinces Rory to let him drive her car, and he crashes it, breaking Rory's wrist. Lorelai becomes furious at Luke for putting Rory in danger by encouraging Jess to study with her, prompting Luke to put Jess on a bus to New York.
Lorelai volunteers her organizational skills to help Richard establish a consulting business. As Rory gradually realizes that everyone in Stars Hollow blames Jess for the accident that led to her broken wrist, her anger and guilt finally lead to an outburst directed at Emily. Meanwhile, Lane discovers a new desire to become a rock drummer when a former New Yorker named Sophie (singer/songwriter Carole King) opens the town's first music store.
As Lorelai frantically prepares for her final examinations in business school, Rory secretly invites townspeople--including Richard and Emily--to Lorelai's graduation ceremony. Christopher gives Lorelai a special gift, and Sookie bakes a cake. Meanwhile, without telling anyone, Rory travels to New York, where Jess has been living since Luke sent him away. Everyone happily gathers for Lorelai's proud moment, but Rory is not there! Her bus is delayed by an accident, and she misses the graduation ceremony. Lorelai is upset until she realizes that Rory truly loves Jess. Rory doesn't believe that she could love anyone but Dean, but she is happy to celebrate Lorelai's graduation with her a little late.
On the eve of Sookie's wedding, Lorelai and Christopher (recurring guest star David Sutcliffe) share an intimate night together. However, their discussion of perhaps resuming their relationship ends when Christopher gets an unexpected message from his former girlfriend. Meanwhile, Rory is so happy to see Jess when he returns to Stars Hollow that she surprises him--and herself--by greeting him with a passionate kiss.
After returning from a summer internship in Washington, D.C., where she mingled with members of the U.S. Congress, preparatory school student Rory Gilmore faces a dilemma with her classmates Dean and Jess. Mariano Lorelai Gilmore, the manager of the historic Independence Inn, is overjoyed to have her daughter home, but upon learning that the girlfriend of Rory's father is having a baby, Lorelai questions her own future. MELISSA McCARTHY stars as Sookie St. James, a clumsy culinary genius and Lorelai's best friend. KEIKO AGENA stars as Lane Kim, Rory's pal. YANIC TRUESDALE stars as Michel Gerard, the inn's haughty concierge. SCOTT PATTERSON stars as Luke Danes, the rugged owner of the local diner who never fails to charm Lorelai with his smile and great coffee. LIZA WEIL stars as brainy and popular student Paris Geller. SEAN GUNN stars as Kirk, one of the town's eccentrics. KELLY BISHOP stars as Emily Gilmore, Lorelai's mother, with EDWARD HERRMANN appearing as Lorelai's father.
Ignoring Lorelai's pleas to stay out of her love life, Emily tries to reunite Rory's father, Christopher (recurring guest star David Sutcliffe), with Lorelai and Rory. This results in an ugly confrontation between Rory and Christopher. Meanwhile, Lorelai rebuffs the romantic advances of the town geek, Kirk, and Rory learns that Jess is angry that she neglected him during the summer.
When an application to attend Harvard University arrives, Rory and Lorelai arrange a dinner at an alumnus' house to get advice. Meanwhile, Lane becomes enamored with a boy who answers her advertisement for rock band members. And local resident Taylor Doose (recurring guest star MICHAEL WINTERS) convinces Luke to open an old-fashioned soda fountain next to the diner.
The Stars Hollow Parent Teacher Association invites Lorelai and Luke to speak at the high school's career day, but when the students bombard Lorelai with questions about her teenage pregnancy, the PTA moms turn ugly. After discovering that her mother, Mrs. Kim (recurring guest star EMILY KURODA), wants her to go to a conservative religious college, Lane asserts her independence by dying her hair purple--with Rory's help.
Lorelai pursues an attractive man, Peyton Sanders (JON HAMM), whom she met at an auction organized by her mother, Emily. However, when the first date is a disaster, Lorelai tries to cancel the second date, and Emily and Richard insist that she is damaging their social standing. Meanwhile, Rory enlists Jess' help when she can't turn off a neighbor's sprinkler system.
When Rory is invited to a celebration for her father's pregnant girlfriend, Sherry (recurring guest star MÄDCHEN AMICK), Lorelai is forced to attend as well, and she inadvertently learns more about Christopher's life than she wanted to know. Meanwhile, after Luke interrogates Jess about where he got the money to buy a used car, he discovers that Jess has a surprising second job.
Lauren Graham
Lorelai Gilmore
Alexis Bledel
Rory Gilmore
Melissa McCarthy
Sookie St. James
Keiko Agena
Lane Kim
Yanic Truesdale
Michel Gerard