After surprising herself by agreeing to go on a fishing date with her new beau, Alex (BILLY BURKE), Lorelai asks Luke for a lesson in fishing techniques. Meanwhile, the political battle between Rory and Paris escalates when Paris tries to have Rory impeached. Lane plots to go to the prom with a guitarist, Dave (recurring guest star ADAM BRODY). And Luke asks an attorney, Nicole (recurring guest star TRICIA O'KELLEY), on a date.

When Christopher's pregnant girlfriend, Sherry (recurring guest star MÄDCHEN AMICK), begins labor and asks Rory to stay with her at the hospital, Lorelai reminisces about the day Rory was born. In flashbacks, 16-year-old Lorelai (CHELSEA BRUMMET) learns she is pregnant, decides not to marry young Christopher (PHILLIP GLENN VAN DYKE) and leaves home with her new baby.

Lorelai goes away with her new boyfriend, Alex (recurring guest star BILLY BURKE), for a weekend in New York, but she worries about leaving Rory and Jess together. Meanwhile, when Jess goes with Rory to dinner at Emily's house and refuses to explain his injured eye, Rory accuses him of fighting with Dean.

Tired of waiting for Jess to call and make plans for the weekend, Rory accompanies Lane to a hockey game, where she encounters Dean and his new girlfriend, Lindsay (ARIELLE KEBBEL). Meanwhile, Lorelai confronts Jess about his poor treatment of Rory. And when Gran (recurring guest star MARION ROSS) comes to visit for a few days, Emily is shocked to find her kissing a man.

While nervously waiting for their college acceptance letters to arrive, Rory and Paris compete to give a speech at Chilton Academy's bicentennial celebration. Meanwhile, when Lorelai encounters her former fiancé, Max Medina (recurring guest star SCOTT COHEN), and they share a passionate kiss, she wonders if ending the engagement was the right decision. Also, Sookie's strange behavior has a surprising explanation.

When a meeting of the Edgar Allan Poe Society at the Independence Inn is interrupted by a minor fire, Lorelai must find rooms for the guests at various homes around town. Forced to relinquish her bedroom in her own house, Lorelai spends the night at Luke's place. Meanwhile, trying to decide amongst Harvard, Yale and Princeton, Lorelai and Rory make an extensive list of positives and negatives for each college. And Luke worries that Jess may not be attending school when he learns that Jess has been working a surprising number of hours at a local drugstore.

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.

With graduation approaching, Rory happily anticipates attending the Stars Hollow High School prom with Jess--but he gets some surprising news from Principal Merten (LAWRENCE HILTON-JACOBS - "Welcome Back, Kotter"). After Lane's rock band debuts at a big party, the evening ends badly when the longstanding animosity between Jess and Dean finally results in a fistfight. Meanwhile, Lorelai reluctantly serves on the parents' committee for the Chilton graduation party, uncomfortably reuniting her with her former boyfriend, Max Medina (recurring guest star SCOTT COHEN).