The Gilmore girls cram one-and-a-half weeks of school shopping and activities into three days so Rory can attend her Yale Orientation. But Luke takes the cake; he got married on the summer cruise he went on with Nicole, but there's more, he's already filing for divorce.
A certain, special student from Chilton is now one of Rory suitemates at Yale. Plus, there is one more surprise; Rory finds she is not quite ready to part from Lorelai.
Lorelai and Sookie start a catering business and their first customer wants a Lord of the Rings themed party. Paris begs Rory to open the door for a Yale party, but ends up regretting it. Richards goes into business with the son of a former associate.
Lorelai starts work on the Dragonfly Inn with no help from Taylor Doose. When Rory returns from Yale for the weekend, she finds out her ex-boyfriend, Dean, is getting married. However, after one too many drinks, Dean confesses to Luke that he still has feelings for Rory.
Rory decides to go out on her first college date and he turns out to be a dud. Meanwhile, Lorelai asks Luke to take Rory's place on the traditional movie night.
Emily begins to plan a cocktail party to launch Richard's new business and hires Lorelai and Sookie as the caterers. But Richard's new business partner, Jason, has different plans. Elsewhere, Kirk gets ready for a date with his brother's ex-girlfriend.
Stars Hollow is busy gearing up to host a festival of living pictures and the town is abuzz. Luke's almost-ex-wife asks him to postpone their divorce, Land and her band find a new guitarist, and with her pregnancy due date past, Sookie is getting anxious.
For the Yale newspaper, Rory is given an assignment to review a ballet performance. Told that it's okay to be opinionated, she takes things a bit too far. Jason joins the group for Friday night dinner and asks Lorelai out on a date.
Rory is invited to the Harvard/Yale football game which leads to a small rift between Emily and Richard. Lorelai agrees to go on a date with Jason and while things start out poorly, things quickly take a turn for the better.
To prove to everyone that he really does love babies, Michel offers to baby-sit Sookie's Davey. However, Davey manages to roll under a bed and Michel calls on Lorelai for help. Elsewhere, Paris is dating a much older school professor.
Lorelai is upset to discover that Luke has gotten an apartment with Nicole, but when it becomes clear that he is reluctant to actually move, Lorelai admits to him that she doesn't want him to leave Stars Hollow. Meanwhile, when Lane sneaks out of the house to play a gig with her band, Mrs. Kim finally discovers her daughter's double life and kicks her out of the house.
Luke is wary when his ditsy sister Liz shows up for an unexpected visit. Lorelai promises Jason that she will tell her parents about their relationship, but changes her mind later. Luke discovers Jess' car is missing and reports it stolen, but discovers that Jess has come back to town to pick up the car.
When Lorelai does Emily a favor by attending a charity dinner, she is pleasantly surprised when Jason also shows up and Emily asks them to pretend they are a couple. Stuck in Stars Hollow while his car is being repaired, Jess keeps running into Rory, but he walks away from her every time they meet.
Although she is completely exhausted by her heavy workload at Yale, Rory is still horrified when a professor suggests she drop a class. Elsewhere, Richard is infuriated when he and Lorelai both get a taste of the nastiness that Gran usually reserves for Emily.
Rory runs into Dean at the Dragonfly Inn and gets a glimpse of his new life. Later, Lorelai and Rory decide to spend a day window-shopping together at the mall, but they run into Emily and are caught up in her wild shopping spree.
When Gran suddenly dies, Richard becomes distraught. While Emily and Lorelai are at Gran's house, sorting through catalogs and bank statements, Emily finds a letter from Gran telling Richard not go through with their wedding and to leave her at the altar. Later, Lorelai has her own small breakdown while buying new underwear for Gran to be buried in.
Paris and Rory head to Florida to celebrate spring break and catch up with old Chilton friends Louise and Madeline. Luke finds out that his Nicole is seeing another man and takes his anger out on the guy's car.
Jason's father, Floyd, brings a lawsuit against Jason and Richard for taking his clients. Floyd also reveals that Jason and Lorelai have been dating secretly for months. Meanwhile, Dean upsets Rory when he admits he has dropped out of college to work full time.
When Jason reveals that he and Richard are no longer in business together, Lorelai has a confrontation with her father. Later, after an uncomfortable Friday night dinner, Lorelai and Rory spy on Emily and make a discovery about the state of the elder Gilmores' marriage. Meanwhile, Luke tells Lorelai that he's getting a divorce.
Depressed over the failure of his marriage, Luke resorts to a self-help tape and realizes that he already knows who his soul mate is. Lorelai is stressed out as opening day at The Dragonfly Inn approaches, and Rory pretends not to be interested when Lorelai tells her she overheard Dean and his wife fighting.
All of Stars Hollow turns out for Liz's wedding. Jess walks her down the aisle, and Lorelai and Luke share a romantic dance, after which Luke asks Lorelai out on a date. Rory attends a drunken party and has to call Dean to drive her back to the dorm.
Lorelai suspects that Luke's intentions toward her have become serious, but she doesn't have time to dwell on it as she prepares for the opening of the Dragonfly Inn. When Jason arrives at the Inn to convince Lorelai that their breakup was a mistake, Luke tries to declare his true feelings for her.