Luke hires Lane to help out at the diner. Rory isn't happy Paris is dating her new teacher. Lorelai and Jason decide to keep their relationship from her parents at least for now and Michel, out of jealousy babysits Davey.
Lane's band gets a gig at famous CBGB's in New York, but it doesn't come without a price. Luke and Lorelai make up to silence the newly restored bells but only after Lorelai realizes maybe Luke hasn't moved completely away and Rory confronts William about their relationship.
Lane fits right in at Yale, almost. Luke's sister Liz visits for her high school reunion and Jess returns to get his car. Meanwhile with Jaime in town, Rory makes Paris decide between her two guys. Lorelai finds money is tight. She and Jason agree to let her parents know they've been dating, but that's easier said than done.
It's firelight festival time again and with Taylor stuck out of town, Kirk tries to fill in. Luke meets his sister Liz's latest boyfriend, Lorelai meets Liz and realizes Luke really is always there for them and Jess, anxious to get out of town as soon as his car is repaired, stirs up trouble with family and friends.
Lane moves in with Lorelai for the time being and lets Mrs. Kim know who advises her to wear socks. Lorelai the first visits and learns that Lorelai's inn construction is costing more then anybody expected. Lorelai and Rory play phone tag as their frustrations mount. Lorelai's financial woes reach a boiling point and so does Rory's school pressures as each have a melt down with the strong married men in their lives.
Kirk tries his hand at dog sitting meanwhile the Gilmore girls are finally able to connect and decide to spend some quality time together window shopping, but with both of them "skint", shopping isn't much fun. The two run into Emily on a shopping binge... angry and upset about her marriage, lack of accomplishments and a little jealous of her daughter.
Lorelai the first passes on suddenly leaving Richard a mess and Emily handling all the arrangements till she discovers a letter Trix wrote Richard the day before he and Emily married. Lorelai finishes up the arrangements the best she can. Luke and Nicole quarrel in the town square and bar glass pinching cousin Marilyn reminisces about Lorelai the First's full life.
Rory and Paris flee from a rainy Dickens-like late winter for a week in Florida for college spring break with the socially awkward Glen and the fitness-freak Janet. There, Rory and Paris meet old school friends Madeline and Louise, the party queens of the area, who give them some pointers for partying, in which Paris goes out of her way to get some attention. Back in Stars Hollow, Lorelai struggles with her growing romance with Jason while she's forced to bail out Luke from jail when he's arrested over stalking his former girlfriend.
Richard and Jason invite Jason's father for dinner only to discover he wants to ruin their competing company. Rory tells Lane what she thinks of Dean's selfish wife, not knowing Lindsay can hear her. And after months of deception, Richard and Emily learn Jason and Lorelai have been dating.
Luke and Nicole finalize their divorce. Lorelai concerned only about Jason, confronts her father on their business problems. Emily too question Richards decisions and gets the cold shoulder which is the final straw for her. Jason then decides to counter sue Richard which leaves Lorelai with only one clear choice.
Liz returns to Stars Hollow with news that she and TJ will marry next week in the towns square which has Luke asking Jess to attend. Lorelai and Sookie overhear Dean and Lindsay's problems and Luke works on his dating and communication skills with a self help tape that makes him realize that the one has been in front of him the whole time!
With Lorelais help, Mrs. Kim and Lane work out their new relationship. Thanks in part to her grandmother, Rory gets stranded on a bad date where she turns to Dean for help. Liz and T.J.'s Renaissance wedding in the town square has Luke and Lorelai enjoying each others company so much so that Luke asks Lorelai for another date and on his way out of town, Jess asks Rory to leave everything and run away with him.
Using the Dragonfly's practice weekend, Lorelai gets her parents to admit they've separated. Meanwhile Luke, doing everything by the book, feels like an idiot when it looks like Jason and Lorelai are still dating, prompting her to clarify the situation to both of them. Meanwhile Rory takes a big step with her first love and Lorelai reminds her he's married.
Tension is still thick between Rory and Lorelai over Dean, so Rory seeks out Lane's perspective and decides to talk to Dean, which leads to more trouble. Lorelai and Luke clarify their new relationship while Emily announces she and Richard have separated. She and Rory decide to head to Europe to escape their problems.
With Lorelai & Rory's relationship still strained and unresolved, Lorelai takes on everything at the inn till Sookie convinces her to take some time off. At the corner of bark and cheese, Rory realizes she was wrong and writes Dean a letter which she asks her mom to deliver. Lane begins to see Zack in a new light and Lindsay finds Rory's letter which leaves Dean out in the cold and without either girl.
Luke and Lorelai enjoy their first official date where Luke tells her he's all in for their relationship. Their new relationship is the basis for the next town hall meeting. Paris has a wake for the passing of her boyfriend and Rory meets a new guy.
Fed up with all the hoops Taylor makes Jackson go through, Jackson decides to run for town selectman with Lorelai and Sookie heading up the campaign only to find that he may not want the job after all. Rory and Dean try to work things out, but have trouble finding a place to be together.
Jackson is overwhelmed by the demands of his new job while Lorelai and Rory decide to see if they can get Richard and Emily back together. With Dean back in the picture, Lorelai tries to make things right with dinner and a movie, but when Pippi Longstocking isn't a good enough distraction for Luke's feelings that Dean isn't good enough for Rory, Lorelai has to bring out the Bop It!.
Rory, desperate for a story idea for the Yale paper, finally decides to research and write about a secret Yale society which happens to have connections to Logan. The Dragonfly Inn's accountant suggests dropping the lunch menu till the money situation improves, which has Sookie upset with the regularly lunching Norman Mailer, who only orders ice tea. With Luke and Lorelai hitting it off, Rory asks her dad to stay out of the picture. Sookie realizes she's pregnant again.
When Emily discovers that Lorelai is dating Luke, she insists he come to dinner. Not to be outdone, Richard invites Luke to a game of golf, and Luke finds himself overwhelmed by the strength of the elder Gilmores' personalities.
Luke tries to smooth things over with Liz and TJ when they stress out about buying a house in Stars Hollow. When Emily learns Rory and Dean are dating again, she calls a temporary truce with Richard to throw a party to introduce Rory to more suitable men. Dean realizes he isn't one of them, and Logan realizes he is.
Jackson has his hands full between Sookie's food cravings and his town selectman duties. Lorelai invites Christopher to lunch, but Rory tells him off and asks Lorelai what Luke thinks of her and Christopher having lunch. Emily decides she's still a viable commodity and asks Lorelai to help her start dating.
Rory is asked to host a Chilton student for a few days at Yale, but the student is more interested in her freedoms than the responsibilities that go with them. Lorelai learns about Luke's dark day, which happens to fall on the same day as Miss Patty's 40th anniversary party. Logan works his way into Rory's life, prompting her and Richard to pull a little prank of their own.