Dean ends his and Rory's relationship on the night of their third anniversary. Refusing to indulge in self-pity, Rory attends a party and finds her classmate Tristin, who just lost his girlfriend. When Tristin kisses Rory, she finally admits to herself how confused and miserable she is. Meanwhile, Lorelai visits Max, and the two can't resist making love.
Emily becomes worried when Lorelai's grandmother offers Lorelai a trust fund for Rory's education. If Lorelai accepts the trust fund, Emily fears she will lose contact with Lorelai and Rory once they are not financially dependent on her. Meanwhile, Rory feels uncomfortable near Tristin after their kiss. She tries to pair Tristin with Paris, not realizing that she herself is the one whom Tristin is interested in.
Aghast to finally see the conditions in which Lorelai reared Rory instead of living with Richard and her, Emily tries to create the perfect bedroom for Rory in her house.
Still upset over Dean, Rory becomes angry with Lorelai, who didn't tell her that she is dating Max again. Dean tells Lorelai that he left Rory because she couldn't say "I love you," and Lorelai urges Rory to express her emotions more freely.
Rory finally tells Dean that she loves him. Rachel senses that Lorelai and Luke are attracted and leaves town rather than pursue Luke anymore. Max also senses the attraction, which Lorelai denies. When Max proposes marriage to Lorelai, she is caught off guard and rebuffs him saying he should have done it the "right" way with 1,000 daisies and a white horse. The next day, Lorelai arrives at the inn to find it full of daisies. Again, Max proposes marriage, and Lorelai considers her response...
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.".
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..."
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.
With the wedding canceled, Lorelai is eager to escape the sympathies of everyone in Stars Hollow, so she and Rory take off on a road trip that ultimately leads to Harvard University. While Rory confronts her dreams of college life, Lorelai ponders what might have been.
Lorelai's well-intentioned advice doesn't dissuade Luke from reluctantly agreeing to care for his wild 17-year-old nephew Jess (new series star Milo Ventimiglia). Rory finds herself attracted to Jess, the town's newest resident.
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.
Lauren Graham
Lorelai Gilmore
Alexis Bledel
Rory Gilmore
Melissa McCarthy
Sookie St. James
Keiko Agena
Lane Kim
Yanic Truesdale
Michel Gerard