Episode 3 : The Hobbit, the Sofa and Digger Stiles
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.
Episode 4 : Chicken or Beef?
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.
Episode 8 : Die, Jerk
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.
Episode 21 : Last Week Fights, This Week Tights
All the townspeople of Stars Hollow come to Liz's (recurring guest star KATHLEEN WILHOITE) Renaissance-themed wedding. Jess (former series star MILO VENTIMIGLIA) walks Liz down the aisle, and Lorelai and Luke share a romantic dance, after which Luke asks Lorelai out on a date. Meanwhile, as Yale students begin their summer break, Rory attends a drunken party and has to call Dean (former series star JARED PADALECKI) to drive her back to the dorm. Dean tries to explain his unhappy marriage to Rory, but they are interrupted when Jess arrives and makes Rory a surprising offer.
Episode 22 : Raincoats & Recipes
Lorelai suspects that Luke's intentions towards her have become serious, but she doesn't have time to dwell on the situation as she prepares for the opening of the Dragonfly Inn by inviting friends and family to a test run. Using the opportunity to force her parents to reconcile, Lorelai is shocked when it becomes obvious that the damage to their marriage is greater than she had thought. When Jason arrives at the Inn to convince Lorelai that their own breakup was a mistake, Luke tries to declare his true feelings for Lorelai. Meanwhile, after their last awkward encounter, Rory attempts to salvage her friendship with Dean (former series star JARED PADALECKI).