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Immediately upon returning from a whirlwind summer backpacking trip to Europe, Lorelai (series star LAUREN GRAHAM) and Rory (series star ALEXIS BLEDEL) Gilmore embark on a heavily scheduled week of mother/daughter activities, in bittersweet anticipation of Rory going away to Yale University as a freshman. But a number of situations conspire to make things harder than expected for them. After an exhausting day of handing out gifts to everyone--except, to Lorelai's dismay, coffee shop owner Luke Danes (series star SCOTT PATTERSON), for whom they couldn't find anything good enough--Rory is horrified to discover that she wrote down the wrong day for her departure. Instead of having a week and a half, they must do everything they had planned within three days. Meanwhile, Taylor Doose opens a soda shop near Luke's diner and, unbeknownst to Rory, hires eccentric resident Kirk to advertise her as the "Ice Cream Queen."
Runtime: 60 minutes Rating: Original Air Date: 9/23/2003
Mother and daughter share Rory's first day at Yale University by moving Rory into her dormitory, where she meets a strange new roommate, Tanna (recurring guest star OLIVIA HACK), and learns that her old adversary, Paris, will also be sharing her room. Although she is overwhelmed with excitement, Rory is also embarrassed to find that she isn't quite ready to let Lorelai go. Meanwhile, Luke continues to cope with the aftermath of a disastrous cruise with his soon-to-be-former wife.
Runtime: 60 minutes Rating: Original Air Date: 9/30/2003
Rory is shocked when Emily completely redecorates Rory's dormitory room without her permission. At her first Yale party, Rory finds herself trapped by twins who were instructed by Emily to find Rory and keep her safe. Meanwhile, Lorelai and Sookie take a job catering a kids' "Lord of the Rings"-themed birthday party to make money while their new inn is under construction. And Richard takes on a new business partner named Jason "Digger" Stiles (series star CHRIS EIGEMAN), who is the son of Richard's former associate.
Runtime: 60 minutes Rating: Original Air Date: 10/7/2003
While visiting Stars Hollow for the weekend, Rory encounters her ex-boyfriend Dean (former series star JARED PADALECKI), who awkwardly invites her to his wedding the next day. During his bachelor party that night, Dean stumbles into Luke's diner and drunkenly confesses how much he misses Rory. Meanwhile, Taylor Doose (recurring guest star MICHAEL WINTERS), who controls the permit procedures for every building in town, irritates Lorelai and Sookie as they try to get construction started on their new Dragonfly Inn.
Runtime: 60 minutes Rating: Original Air Date: 10/14/2003
Rory goes on her first date since ending her relationship with Jess and finds that college dating is not going to be easy. Lorelai invites Luke over for the traditional movie night she used to share with Rory. Later, Lorelai gets upset when she learns that the designer she just hired for the Dragonfly Inn used to work for Emily.
Runtime: 60 minutes Rating: Original Air Date: 10/21/2003
When Emily plans an elaborate launch party for Richard's new company, she hires Lorelai and Sookie to cater the affair but insists they prove that they are worthy of her trust. After Richard's partner, Jason "Digger" Stiles, insults Emily by suggesting that her party idea is outdated, Lorelai confronts him and is surprised when he asks her out to dinner. Meanwhile, Rory has a tough time finding a decent place to study at Yale.
Runtime: 60 minutes Rating: Original Air Date: 10/28/2003
Stars Hollow hosts the Festival of Living Art an event in which the townspeople dress up and present tableaux imitating famous paintings.
Runtime: 60 minutes Rating: Original Air Date: 11/4/2003
When the editor of the Yale student newspaper tells Rory that her articles are dull, she writes a scathing review of the Yale ballet and becomes the vindictive lead ballerina's target. Jason impresses Lorelai by manipulating Emily into inviting him to Friday night dinner so he can continue flirting with Lorelai. Meanwhile, surprised to see Nicole (recurring guest star TRICIA O'KELLEY) at the diner, Lorelai forces Luke to admit that he and Nicole have put their divorce on hold and are dating again. And Lane gets upset when her mother gives her a "marriage jug" to send to her boyfriend in California.
Runtime: 60 minutes Rating: Original Air Date: 11/11/2003
After Richard and Emily invite Rory and Lorelai to their fancy tailgate party at the Harvard/Yale football game, Lorelai's innocent conversation with Richard's ex-fiancée, Pennilyn Lott (LINDA GEHRINGER), leads Emily to realize that Richard and Pennilyn have been meeting secretly for lunch for many years. Emily berates both Richard and Lorelai, prompting Lorelai to stop worrying about her mother's feelings and finally accept Jason's invitation to dinner instead of staying at Emily's party. Meanwhile, Richard introduces Paris to his former classmate Asher Flemming (recurring guest star MICHAEL YORK - "Austin Powers" movies), who is now a distinguished Yale professor. Later, Rory is astonished when she later spots Paris and the professor kissing.
Runtime: 60 minutes Rating: Original Air Date: 11/18/2003
While Lorelai and Sookie work on renovating their new inn, Michel clashes with a rival who he believes wants the manager position.
Runtime: 60 minutes Rating: Original Air Date: 1/20/2004