SEASON TWO
"SADIE, SADIE..."
Lorelai tells Luke Max proposed to her, but when he grills her about their future plans, she gets angry. Later, at the
Friday night dinner, Lorelai calls Max and accepts his marriage proposal. The next Friday night Rory brings Dean to dinner at her grandparents' house, and Richard's obvious disapproval of Dean leads to the first fight between Rory and her grandfather. When Emily hears about the upcoming wedding from Sookie, she is hurt that Lorelai didn't bother to tell her.
"HAMMERS AND VEILS"
"Hammers and Veils" is the second part of a two-hour episode that begins with "Sadie, Sadie..." When Lorelai finally tells
Emily she and Max are going to get married, Emily tells her she will attend if they aren't busy. When Lorelai tells Luke about the rebuff she got from Emily, he proceeds to tell her how screwed up weddings and marriages can be. Rory helps build a house to get
extracurricular credits for Harvard. After dinner with Max, Lorelai makes him drive to the
Gilmore's where she yells at Emily for not being happy for her. And Emily tells her how hurt she was that she had to hear about Lorelai's wedding from Sookie. The town throws Lorelai and Max an engagement shower/party.
"RED LIGHT ON THE WEDDING NIGHT"
During a wild bachelorette party hosted by Sookie, Lorelai makes an impulsive telephone call to Christopher. That night she tells Rory to pack for a road trip when she realizes that Max is not the man for her.
"THE ROAD TRIP TO HARVARD"
With the wedding canceled, Lorelai and Rory take off on a road trip. They stay in a
flowered-themed B&B. They visit Harvard University. While Rory confronts her dreams of college life, Lorelai ponders what might have been.
"NICK & NORA/SID & NANCY"
Lorelai's well-intentioned advice doesn't dissuade Luke from reluctantly agreeing to care for his wild 17-year-old nephew Jess. Rory finds herself attracted to him.
"PRESENTING LORELAI GILMORE"
Emily requests that Rory partake in a debutante ball. To everyone's surprise, Rory agrees. After asking Christopher to present Rory to society, Lorelai finds herself attracted to the new, more responsible man he has become.
"LIKE MOTHER, LIKE DAUGHTER"
Rory is told by her guidance counselor that she is perceived as a loner, and her subsequent, reluctant efforts to socialize put her in the most popular clique, the Puffs, at Chilton. Meanwhile, the chancellor of Chilton recommends that Lorelai participate more in school activities, so she volunteers the Inn as a venue for a Chilton fund-raising fashion show. She is later to find herself modeling matching outfits with her Emily.
"THE INS & OUTS OF INNS"
Lorelai and Sookie have the first fight of their long friendship when, upon hearing that the Independence Inn may be sold, Lorelai panics and decides that their shared dream of opening an inn together is doomed to fail.
"RUN AWAY LITTLE BOY"
When Rory and her classmate Tristin are cast as Romeo and Juliet in a school play, a jealous Dean insists on attending every rehearsal, forcing Rory to beg
Tristin not to tell Dean about the time she and Tristin kissed, which he does anyway. Meanwhile, Lorelai has to endure Luke's teasing after she dates a much younger guy, causing bad feelings between them. Sookie tells
Lorelai Luke is hurt because Lorelai will apparently date anyone but him.
"THE BRACEBRIDGE DINNER"
While Rory struggles to keep the budding rivalry between Dean and Jess under control, Lorelai invites most of the citizens of Stars Hollow to an elaborate feast, complete with Elizabethan costumes and horse-drawn sleigh rides. During the event, Richard stuns Emily by revealing that he has retired.
"SECRETS AND LOANS"
Lorelai is concerned because she can't afford to repair her home's extensive termite damage. Luke offers her $15,000, but she refuses. She becomes angry when Rory tells Emily about the problem, and Emily offers Lorelai a loan. She refuses, but ends up taking out a loan at Emily's bank with Emily co-signing. Meanwhile, Rory is confused when Lane joins the cheerleading squad, despite having always mocked it.
"RICHARD IN STARS HOLLOW"
Newly retired Richard is making Emily crazy, so Lorelai agrees to take her father for a day in Stars Hollow, where he proceeds to annoy both Lorelai and Rory. Richard criticizes every aspect of their lives and refuses to let Rory accept a car that Dean built for her.
"A-TISKET A-TASKET"
The annual Stars Hollow Picnic Basket Auction causes romantic complications when Jess outbids Dean to win a picnic lunch date with Rory. A fight ensues between Rory and Dean, and she has an even bigger argument with Lorelai over Rory's socializing with Jess. When Miss Patty brings in three guys to bid over Lorelai's basket, she panics and gets Luke to out-bid them. They sit in the gazebo together and talk about each other maybe having kids when the 'right one' comes along.
"IT SHOULD'VE BEEN LORELAI"
Lorelai and Rory are stunned when Christopher brings his new girlfriend, Sherry, to Stars Hollow. Sherry makes it obvious that she wants to build a meaningful relationship with Rory. Meanwhile, when Emily learns about Sherry, she becomes furious with Lorelai for failing to win Christopher back.
"LOST & FOUND"
Rory panics when she realizes that she has lost the bracelet that Dean made for her. When the suspicious Lorelai witnesses Jess in Rory's room, she accuses him of stealing. Meanwhile, exasperated with sharing his cramped apartment over the diner with Jess, Luke impulsively buys the entire building in order to expand.
"THERE'S THE RUB"
Lorelai and Emily are at a health spa for the weekend, but they sneak out for some unauthorized food at a local restaurant. There, Emily dances with a distinguished stranger, Chad, and blames Lorelai for her feelings of guilt. At home, Rory looks forward to a rare evening alone, but problems occur when Paris, Jess and Dean all come to the house unexpectedly.
"DEAD UNCLES & VEGETABLES"
Luke is overwhelmed by the funeral arrangements he must make for his deceased Uncle Louie, who was Stars Hollow's most disliked citizen, so Lorelai and Rory work at Luke's, without much help from Jess. Meanwhile, Emily's extravagant suggestions for Sookie's upcoming wedding to Jackson make everyone crazy.
"BACK IN THE SADDLE AGAIN"
When Chilton hosts its annual business fair, Rory must create and market a first-aid kit for teenagers, so she asks newly-retired 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, visits town. And Dean feels miserable when he suspects that Rory is no longer romantically interested in him.
"TEACH ME TONIGHT"
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. Luke fires back at her for blaming him for Jess being there. Luke puts Jess on a bus to New York.
"HELP WANTED"
When Lorelai and Rory get to the diner, it's closed with a Gone Fishing sign on it. Lorelai thinks it's because of the fight she and Luke had over Rory's broken wrist. 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 leads 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.
"LORELAI'S GRADUATION DAY"
As Lorelai frantically prepares for her final examinations in business school, Rory secretly invites Richard and Emily to Lorelai's graduation ceremony. Christopher gives Lorelai a special gift basket, and Sookie bakes a cake. Meanwhile, without telling anyone, Rory skips school and 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. Lorelai tells Rory she still wants to celebrate her graduation with her.
"I CAN'T GET STARTED"
On the eve of Sookie's wedding, Lorelai and Christopher share an intimate night together. However, their discussion of perhaps resuming their relationship ends when Christopher gets an unexpected message from his former girlfriend. He tells Lorelai Sherry is pregnant and has to go to her. 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.