Lorelai and Rory return from their summer backpacking trip to Europe only to discover Rory miscalculated how much more time she had off till school starts which puts her in a bind with Taylor and Lorelai in a bind with Emily. Luke's summer cruise with Nicole got him in a bind and Sookie is almost ready to have her baby.
Always willing to help, Luke lends his truck to Lorelai to get Rory moved into her dorm despite how much trouble it turns out to be. Meanwhile, the Gilmores realize Rory is growing up, but Lorelai helps her ease into her new life. Paris turns out to be one of Rory's new roommates and not by accident. Luke has to deal with his pending divorce.
To earn some money before the baby arrives, Sookie asks Lorelai if they can cater a kids party but Sookie doesn't know what kids like. Emily sets Rory up the proper way and Richard contemplates a business partner.
After reflecting on her lack of social life, Rory decides to try dating and finds it harder than it looks. Lorelai is still adjusting to an empty house and has Luke over to try to fill the gap. Meanwhile Lorelai is somewhat disturbed after discovering that the designer she just hired to decorate the inn used to work for Emily.
Stars Hollow is asked to host a Festival of Living Pictures when a neighboring town backs out, inspiring the town regulars pitch in to pull it off in only a week. Lane finds the perfect guitarist to replace Dave, but Zach objects because of his age. Sookie and Jackson hire one of the best midwifes on the eastern seaboard. Luke and Nicole decide to hold off on their divorce.
After receiving advices from the Yale Daily News editor on what he is looking for, Rory's next article is a huge hit with everybody except the dancer she reviewed. Richard and Emily return from their Atlantic City business trip while Lane is told to send a special jug to Dave in California. Lorelai confronts Luke about his relationship with Nicole and Bruce confronts Lorelai and her anti midwife energy on retarding the baby's acquisition rate.
At lunch, Richard introduces Rory and Paris to his old friend who Paris is more than intrigued with. Meanwhile it's time for the Yale/Harvard game and the Gilmores go in style, happy flask and all till Emily realizes she's been deceived for many years which inadvertently pushes Lorelai into the arms of Jason.
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 Deans 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 Lorelai is the one.
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 Tj'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.