Brian Berke

While Lorelai deals with the rebuilding of the fire-damaged inn, Rory schemes to give her mom a great birthday party, complete with a gigantic pizza. After Richard surprises Lorelai with a large check that resulted from an investment he made when she was born, she uses part of the money to repay her parents for Rory's education, a gesture which does not please Emily. Meanwhile, Luke confirms that his suspicions are correct: Jess has been skipping school to work extra shifts at the drugstore.

Stars Hollow hosts the Festival of Living Art, an event in which the townspeople dress up and present tableaux imitating famous paintings. Rory appears in Portrait of a Young Girl Named Antea. Lorelai plays the beauty in Renoir's The Dance at Bougival. And Kirk is Jesus in The Last Supper, along with the Town Troubadour (recurring guest star GRANT LEE PHILLIPS) as Judas. Meanwhile, Sookie panics because she hasn't given birth by the date she's supposed to, and Lorelai calms her with stories of the night Rory was born. Luke's wife, Nicole (recurring guest star TRICIA O'KELLEY), tells Luke that she wants to postpone their divorce and give their relationship a chance. And Lane finds a great guitarist, Gil (SEBASTIAN BACH of the band Skid Row), but he is a lot older than everyone else in the band.

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 encounters Dean (former series star JARED PADALECKI) for the second time at the Dragonfly Inn and gets a glimpse of his new life. Later, Lorelai and Rory decide to spend a day together at the mall, but they run into Emily and are caught up in her wild shopping spree. When Lorelai questions her mother on her out-of-control spending, Emily admits that she is getting revenge on Richard, who has been ignoring her to concentrate on his new business. Meanwhile, although Lane is excited to be moving into her first apartment with two of her band mates, she is also hurt by her mother's (recurring guest star EMILY KURODA) coldness.

Jason's father, Floyd (LAWRENCE PRESSMAN - "American Pie" movies), sues Jason and Richard for taking his clients. Floyd also reveals that Jason and Lorelai have been dating secretly for months. Meanwhile, Dean (former series star JARED PADALECKI) upsets Rory when he admits he has dropped out of college to work full time so he and his wife, Lindsay (recurring guest star ARIELLE KEBBEL), can buy a townhouse. Lindsay demands that Dean stop associating with Rory, but Dean and Rory plan to secretly remain in contact.