Still smarting from her split with Luke, Lorelai is further stung when she notices that Luke has moved his boat. Meanwhile, Luke volunteers to build the sets for a school production of ""Fiddler on the Roof,"" knowing that Lorelai is doing costumes, in hopes that their paths will cross. Meanwhile, at Yale, Rory plans to reconnect with Marty (Wayne Wilcox) to watch Marx Brothers movies, but Logan interrupts their day by inviting them to dinner with his group.

Luke answers Lorelai's question and as news of Luke's reply leaks to the denizens of Stars Hollow, the untraditional proposal stirs up more talk than the answer itself. Richard and his lawyer go to bat for Rory in court for her yacht incident, but the judge is tougher than expected.

Rory is pleasantly surprised when her old flame Jess appears at her grandparents' house and reveals an amazing development in his life. Rory agrees to go to dinner with Jess, and when Logan unexpectedly joins them, an ugly confrontation develops, leaving both Rory and Logan to face the choices they have made. Emily is concerned about Rory's sudden evasiveness and tries to exert some parental discipline. Meanwhile, Luke agrees to sponsor a local girls’ soccer team and Lorelai channels all her concerns about Rory into caring for her dog, Paul Anka

Lane and Zack's wedding is coming up and since Luke is busy, Michel is Lorelai's first choice as a date for Lane and Zack's wedding, but he gets Celine Dion tickets and bails. Rory suggests that Chris go as Lorelai's date and Chris is totally psyched to do it. Grandma Kim is a Buddhist and doesn't know that Mrs. Kim is a 7th Day Adventist. At Lane's wedding, Lorelai collapses and Christopher is there to take care of her.