As the relationship with Rory's teacher Max grows more serious, Lorelai panics and decides to end it, but her attempt to break up with him during Parent-Teacher night at Chilton causes even more trouble at school for Rory.
Two double dates. Rory and Dean set up Lane with Dean's friend and the four go out. Meanwhile Sookie and Jackson's first date includes Lorelai and Jackson's cousin, who's very very weird. Lorelai does not enjoy the evening.
Christopher visits the Hollow for the first time and Rory shows him off and shows him the town. Dinner with the parents ends up with both Rory's grand parents fighting. After talking up his business venture, Lorelai gets Christopher to admit he's failing and has him proposing before leaving town.
In one of the highest rated shows, Lorelai is becoming seriously involved with Max just as she finds herself getting in the middle of another relationship when Luke's girlfriend Rachel accuses him of being in love with Lorelai. Meanwhile, Rory has her own romance drama and tries to work up the courage to win Dean back.
Lorelai accepts Max's proposal, but when Emily hears about the upcoming wedding from Sookie, she is hurt and angry that Lorelai didn't bother to tell her. 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.
Lorelai avoids telling her parents about her engagement to Max, while Rory urges her to spill. But due to a call from Sookie asking them to come to a surprise wedding shower for the happy couple, they already know, and are appalled that Lorelai didn't tell them and so they give her the cold shoulder. Meanwhile, Rory and Dean are having trouble in paradise due to the fact that Rory suddenly becomes obsessed with finding enough extracurricular activities that will set her apart from the hundreds of other Harvard applicants.
The Gilmore Girls' road trip takes them to a most unusual bed and breakfast and more importantly to tour Harvard and Rory's possible future. Meanwhile Lorelai decides to move forward with her dream of opening an inn.
Rory surprises everyone by agreeing to Emily's request that she make her debut at a Debutante Ball, and when Lorelai asks Rory's dad Christopher to present his daughter to society, she finds herself attracted to the new, more responsible man he has become.
Chilton's headmaster Charleston thinks Rory isn't properly socializing and when Lorelai disagrees he tells her Rory may be taking after her mom. Rory's attempt to reach out gets her involved with a sorority while Lorelai becomes a booster.
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 failure.
When Rory and Tristan 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 they shared a kiss, while Lorelai has to put up with Luke's teasing after she dates a much younger guy.
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 which Richard announces to Emily that he has retired.