Episode 1 : Sadie, Sadie
Lorelai accepts Max Medina's (recurring guest star Scott Cohen) marriage proposal, but when Emily hears about the upcoming wedding from Sookie, the elder woman is hurt and angry that Lorelai didn't bother to tell her. Soon, the whole town is busy making wedding arrangements, but her mother's attitude dampens the bridal bliss for Lorelai. Meanwhile, Rory brings Dean to dinner at her grandparents' house, and Richard's obvious disapproval of Dean leads to the first fight between Rory and her grandfather. "Sadie, Sadie..." is the first part of a two-hour episode that concludes with "Hammers and Veils.".
Episode 2 : Hammers and Veils
Lorelai accepts Max Medina's (recurring guest star Scott Cohen) marriage proposal, but when Emily hears about the upcoming wedding from Sookie, the elder woman is hurt and angry that Lorelai didn't bother to tell her. Soon, the whole town is busy making wedding arrangements, but her mother's attitude dampens the bridal bliss for Lorelai. Meanwhile, Rory brings Dean to dinner at her grandparents' house, and Richard's obvious disapproval of Dean leads to the first fight between Rory and her grandfather. "Hammers and Veils" is the second part of a two-hour episode that begins with "Sadie, Sadie..."
Episode 3 : Red Light On the Wedding Night
During a wild bachelorette party hosted by Sookie, Lorelai makes an impulsive telephone call to Rory's father, Christopher (recurring guest star David Sutcliffe), and sadly realizes that Max is not the man for her. Sally Struthers ("All in the Family") guest stars.
Episode 6 : Presenting Lorelai Gilmore
Emily requests that Rory partake in a debutante ball. To everyone's surprise, Rory agrees. After asking Rory's father, Christopher, to present Rory to society, Lorelai finds herself attracted to the new, more responsible man he has become.
Episode 8 : The Ins and Outs of Inns
Lorelai and Sookie have the first fight of their long friendship when, upon hearing that the Independence Inn may be sold, Lorelai panics and decides that their shared dream of opening an inn together is doomed to fail.
Episode 9 : Run Away, Little Boy
When Rory and her classmate Tristan (recurring guest star Chad Michael Murray) are cast as Romeo and Juliet in a school play, a jealous Dean insists on attending every rehearsal, forcing Rory to beg Tristan not to tell Dean about the time she and Tristan kissed. Meanwhile, Lorelai has to endure Luke's teasing after she dates a much younger guy.
Episode 10 : The Bracebridge Dinner
While Rory struggles to keep the budding rivalry between Dean and Jess under control, Lorelai invites most of the citizens of Stars Hollow to an elaborate feast, complete with Elizabethan costumes and horse-drawn sleigh rides. During the event, Richard stuns Emily by revealing that he has retired.
Episode 11 : Secrets and Loans
Lorelai is concerned because she can't afford to repair her home's extensive termite damage. She becomes angry when Rory tells Emily about the problem, and Emily again offers Lorelai a loan. Meanwhile, Rory is confused when Lane joins the cheerleading squad, despite having always mocked it.
Episode 19 : Teach Me Tonight
Luke asks Rory for help after he learns that Jess is failing several high school classes. However, during their first study session, Jess convinces Rory to let him drive her car, and he crashes it, breaking Rory's wrist. Lorelai becomes furious at Luke for putting Rory in danger by encouraging Jess to study with her, prompting Luke to put Jess on a bus to New York.
Episode 22 : I Can't Get Started
On the eve of Sookie's wedding, Lorelai and Christopher (recurring guest star David Sutcliffe) share an intimate night together. However, their discussion of perhaps resuming their relationship ends when Christopher gets an unexpected message from his former girlfriend. Meanwhile, Rory is so happy to see Jess when he returns to Stars Hollow that she surprises him--and herself--by greeting him with a passionate kiss.