Julie Dolan

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.

While calling Lorelai from Rome, Rory admits that she complicated her relationship with Dean (recurring guest star JARED PADALECKI). Lorelai gives Dean a letter from Rory, but Dean's wife, Lindsay (recurring guest star ARIELLE KEBBEL), finds the letter and makes Dean move out of the house. Rory returns from Europe, and a terrible argument ensues when she and Lorelai encounter Lindsay and her mother. Meanwhile, Luke returns to Stars Hollow after spending several weeks helping his injured sister, Liz (recurring guest star KATHLEEN WILHOITE), on the Renaissance Fair circuit. Luke and Lorelai try to find a private spot to say hello but are interrupted by a town parade.

Rory and Dean have difficulty meeting alone because they live far apart and Dean (recurring guest star JARED PADALECKI) shares a car with his estranged wife. Impulsively, Rory asks Dean if he left his wife because Lindsay found Rory's letter--and she is not completely satisfied with his response. Lorelai and Sookie manage Jackson's (recurring guest star JACKSON DOUGLAS) campaign when he decides to compete against Taylor (recurring guest star MICHAEL WINTERS) for town selectman. Lane tells her band mate Zach (recurring guest star TODD LOWE) that she has feelings for him.

Stranded in Stars Hollow while his car is being repaired, Jess (recurring guest star MILO VENTIMIGLIA) keeps crossing paths with Rory--but he walks away from her every time. Luke tries to talk to Jess about Liz (recurring guest star KATHLEEN WILHOITE), Luke's sister and Jess' mother, who is dating someone new. However, Jess angrily tells Luke to stop interfering in other people's lives. Lorelai does a favor for Emily by attending a charity dinner and is pleasantly surprised when her secret boyfriend, Jason, arrives--and the unsuspecting Emily asks them to "pretend" they are a couple. Meanwhile, when Rory and Jess encounter each other for a third time, Rory tries to be the one who walks away, but Jess stops her and makes a shocking confession.

Rory begins to work her 300 hours of community service and finds that life on a road crew is not pretty. Lorelai and Luke try to decide whether they will fix up Lorelai's home or buy the Twickham house, which Luke has always admired. Luke's sister, Liz (recurring guest star KATHLEEN WILHOITE - "ER"), begs him to hire her husband, T.J. (recurring guest star MICHAEL DeLUISE - "NYPD Blue"), as a contractor. When Rory surprises Luke with a visit at the diner to find out how Lorelai is, he feels obligated to tell her that he and Lorelai are engaged. Afterwards, Luke confronts Lorelai about her estrangement from Rory. Feeling lonely, Lorelai adopts a dog at the Stars Hollow pet fair. Finally, during a chance meeting, Lorelai and Rory have an angry confrontation about their mutual hurt feelings.