2x01 "Sadie, Sadie" | October 9, 2001
Lorelai accepts Max's proposal, but when Emily hears about the upcoming wedding from Sookie, she is hurt and angry that Lorelai didn't bother to tell her. Meanwhile, 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.

2x02 "Hammers and Veils" | October 9, 2001
Rory stresses out about being too far behind on extracurriculars, which puts a strain on her relationship with Dean. Hurt over being the last to know, Emily gives Lorelai a frigid reception when her daughter finally tells her the good news. All of Stars Hollow turns out for Lorelai's and Max's engagement party.

2x03 "Red Light on the Wedding Night" | October 16, 2001
During a wild bachelorette party thrown by Sookie, Lorelai makes an impulsive phone call to Rory's dad Christopher and sadly realizes that Max is not the man for her.

2x04 "The Road Trip to Harvard" | October 23, 2001
To escape everyone's reaction to the news of the broken engagement, Lorelai and Rory hit the road, and stumble upon the bed and breakfast from hell before eventually arriving at Harvard, where Rory gets a taste of college life and Lorelai muses over what might have been. Lorelai decides to get serious about making her dream of opening an inn a reality.

2x05 "Nick & Nora/Sid & Nancy" | October 30, 2001
When Luke's rebellious 17-year-old nephew, Jess moves in with him, Lorelai offers unwelcome parenting advice. Rory's on the school newspaper staff, but editor Paris is still mad due to her supposed "date" with Tristan.

2x06 "Presenting Lorelai Gilmore" | November 6, 2001
At the urging of her friends, Emily decides that Rory making her debut at a society ball will be just the thing to get Richard back into the social swing. To Lorelai's amazement, Rory willingly agrees and Emily goes into high gear shopping in preparation. Christopher agrees to escort Rory and Lorelai becomes entranced by his new responsible side, but gets a shock when she learns about his new relationship.

2x07 "Like Mother, Like Daughter" | November 13, 2001
Headmaster Charleston decrees that both Gilmore girls need to improve their socialization skills at Chilton if they want him to write a glowing recommendation for Rory's Harvard application. Rory accidentally tangles herself up in a secret sorority known as The Puffs, and however unwanted the connection is; it reconciles Paris and Rory's damaged relationship. After being chided by Emily for her lack of participation, Lorelai joins the Booster Club and offers to host a fundraising fashion show at the Inn.

2x08 "The Ins and Outs of Inns" | November 20, 2001
Lorelai and Sookie gear up their plans to open an inn, but encounter a roadblock when the owner of their dream location refuses to sell the property. The unexpected arrival of Mia, the absentee owner of the Independence Inn, complicates matters even further when Lorelai begins to experience pangs of guilt at leaving Mia with the responsibility of running the Inn again. Lorelai's emotional turmoil culminates with having her first ever argument with Sookie.

2x09 "Run Away Little Boy" | November 27, 2001
Tristan and Rory must play Romeo and Juliet in a school project, and Dean is peeved on the matter; yet the night of the performance Tristan is sent to military school. Meanwhile, Lorelai dates a much younger business school classmate, much to Luke's amusement.

2x10 "The Bracebridge Dinner"| December 11, 2001
A blizzard prevents a group from attending the historical dinner that Sookie has painstakingly prepared at their request, so she and Lorelai decide to invite all their friends in Stars Hollow to enjoy the feast at the Inn. At Rory's urging, Lorelai also invites Richard and Emily, in an attempt to boost Richard's spirits. During dinner, Emily is hurt and angered when Richard reveals that he has quit his job without consulting her.

2x11 "Secrets and Loans" | January 22, 2002
Lorelai and Rory have a major falling out after Rory goes against her mother's wishes and asks her grandparents to lend Lorelai the money she needs to repair termite damage to their house.

2x12 "Richard in Stars Hollow" | January 29, 2002
Richard visits Stars Hollow, and drives Lorelai and Rory crazy by passing judgment on every aspect of their lives.

2x13 "A-Tisket, A-Tasket" | February 5, 2002
During the annual Stars Hollow charity picnic basket auction, both Lorelai and Rory's baskets have more competition then they both anticipated. Meanwhile Jackson refuses to bid on Sookie's basket leading them to work on their communication. Rory and Lorelai have their own communication problems but work it out after Emily sides with Lorelai's initial reaction to Jess worming his way into Rory's life.

2x14 "It Should Have Been Lorelai" | February 12, 2002
Christopher and his girlfriend Sherry visit Stars Hollow leading Sherry to push for a Friday night out alone with Rory to bond. So Lorelai takes Christopher to a tumultuous Friday night dinner at her parents. Lorelai, thinking she missed out on a life with Christopher, confesses her self-realization.

2x15 "Lost and Found" | February 26, 2002
Rory panics when she suddenly realizes that she lost the bracelet Dean made for her, and when a suspicious Lorelai catches Jess in Rory's room, she accuses him of stealing the bracelet. Meanwhile, Luke goes a little stir-crazy after living with Jess in the tiny apartment over the diner, and he impulsively buys the building so he can expand.

2x16 "There's the Rub" | April 9, 2002
When Emily and Lorelai go to a spa for a weekend of relaxation, Emily lets her hair down, kicks up her heels and ends up bonding with Lorelai in a way that only her daughter could inspire. Thrilled that she has the house all to herself, Rory hopes to spend a quiet night at home doing laundry and eating Indian food. Her plans are foiled -- first by Paris, then by Jess, and finally by Dean.

2x17 "Dead Uncles and Vegetables" | April 16, 2002
Luke's uncle dies, but the funeral is poorly attended, as nearly everyone has a grudge against the antisocial old man; Luke worries he has followed his uncle's example. Emily helps Sookie plan her wedding, and it becomes too much for Jackson. Emily tells Lorelai that she and Luke are a match made in heaven.

2x18 "Back in the Saddle Again" | April 23, 2002
Rory asks Richard for help in creating and marketing a first-aid kit for Chilton's annual Business Fair, which leads him to realize that he is unhappy in retirement and wants to start a second career. Dean goes overboard in trying to be close to Rory, afraid that she is losing interest in him, and finally becomes resigned to her affection for Jess.

2x19 "Teach Me Tonight" | April 30, 2002
Against her better judgment, Lorelai agrees to Luke's request that Rory tutor an about-to-flunk-out Jess. Rory and Jess decide to take a break from studying to get some ice cream, and with Jess behind the wheel, get into a car accident which leaves Rory with a broken wrist and a totaled car. A distraught Lorelai blames Luke for the accident, creating a serious rift in their relationship. Christopher arrives in the middle of the night ready to go after Jess, but Jess has already left Stars Hollow to return home.

2x20 "Help Wanted" | May 7, 2002
Richard opens a new office and hires a secretary with Lorelai's help. Lane falls in love with a drum set at Stars Hollow's new music shop and discovers that becoming a rock drummer is her new dream in life. Rory is dismayed to discover that everyone blames Jess for the accident despite her protestations.

2x21 "Lorelai's Graduation Day" | May 14, 2002
Lorelai and Rory have breakfast at Sookie's in an effort to avoid Luke's, but Lorelai can't avoid an awkward encounter with him at Doose's Market, where he fails to pick up on her hints to patch things up. Lorelai is shocked to see Emily, Richard attend her graduation from business school. Rory misses the ceremony in order to visit Jess in New York and find out why he never said goodbye.


2x22 "I Can't Get Started" | May 21, 2002
It is Sookie's and Jackson's wedding day. Christopher breaks up with Sherry, and spends a romantic night with Lorelai at the Inn, after which they make plans to reunite and be a family. When Chris discovers the next day that Sherry is pregnant with his child, he tells Lorelai he cannot follow the same footsteps with the new baby the way he did Rory. Lorelai tries to make amends with Luke, but fails. Rory is surprised to see Jess at the wedding; kissing him before running off.