Headmaster Charleston decrees that both Gilmore girls need to improve their socialization skills at Chilton if they want him to write a glowing recommendation for Rory's Harvard application. Rory's first attempt to socialize leads her to ask a group of girls at lunch if she could join them. They agree and hit it off famously. After lunch, an insanely jealous Paris accosts Rory and tells her the group that she innocently stumbled into is "The Puffs", Chilton's famed secret sorority. Paris would do anything to join, and she begs Rory not to bad-mouth her to the group. At the next opportunity, Rory talks Paris up to the group and they are both accepted as pledges. The Puffs "kidnap" Rory, Paris and the other pledges very early one morning under the guise of taking them to breakfast, but instead take them to Headmaster Charleston's office to be initiated into the group. In the middle of the ceremony, they are discovered by Charleston and the security guards. He calls their parents and threatens their college careers, until Rory stands up to him and says that if he hadn't forced her to socialize, she wouldn't be there at all. He agrees and reconsiders, saying that she is a good student who deserves to go to Harvard. After being chided by Emily for her lack of participation, Lorelai joins the Booster Club and offers to host a fundraising fashion show at the Inn. To her dismay, she discovers that the Booster Club mothers are the models; not wanting to be mortified by herself, and to exact a little payback for being chided, she signs Emily up to model as well. On the day of the show, Lorelai calls Luke to fix the runway, and he catches the eye of Eva, the Booster Club president, who's quite taken with him. Lorelai becomes uncomfortable when she sees them huddled together talking. The day goes even further downhill when Lorelai discovers that she and Emily will be modeling matching mother-daughter outfits. They end up looking terrific and having a ball struting their stuff on the runway, and the show is a tremendous success. Back in Stars Hollow, Lorelai visits Luke at the diner and asks him not to go out with Eva. She offers the pathetic reason that she wants to keep her Stars Hollow life and her Chilton life separate, and that Luke's dating Eva will combine the two. Luke sees right through her, and after letting her know that he'll date whoever he pleases, tells her that he's not interested in Eva and was only giving her directions back to Hartford. Lorelai, secretly happy but realizing she's made a fool of herself, hurries out of the diner, to Luke's amusement.

Lorelai receives a late wedding present without a card attached, and insists that it be returned. Sookie sees to what great lengths Lorelai is going to find out who sent it, and tells Lorelai to move forward in life to get some closure on her relationship with Max. Lorelai takes her advice and accepts a dinner date with Paul, one of the other students in her business class. The date goes well, but they decide to remain friends because they don't have very much in common. When Paul appears at Luke's the following Saturday with his parents in tow, Lorelai gets ribbed by everyone in town because he's so young. Luke is uncharacteristically quiet, which Lorelai can't figure out until Sookie explains that he's had a crush on Lorelai forever. Lorelai goes to him to let him know that he'll always be a very important part of her life, and Luke brightens up again. Rory, Paris, Madeline and Louise are assigned to present the death scene from "Romeo and Juliet" as part of ther class participation in the Chilton Shakespearean Festival. Since this production will account for half of their grade, Paris takes over as director and assigns Rory the role of Juliet. Tristan returns to school with Duncan and Bowman after their suspension, and is cast as Romeo against Rory's wishes. When a scheduling mixup occurs with the rehearsal hall, Rory is horrified to learn that Paris has rented Miss Patty's studio and that the group will convene in Stars Hollow to practice. Tristan wastes no time in going to the market and taunting Dean, and they nearly come to blows before Rory pulls them apart. The next day at school, Rory pleads with Tristan not to mention anything to Dean about their kiss at the party, because it meant nothing to her. She also cautions him about hanging out with Duncan and Bowman. Stung by her words, but hiding it well, Tristan storms off. The next day Dean shows up to watch rehearsal and Tristan taunts both Dean and Rory before he finally bails to go off with Duncan and Bowman. On the evening of the performance, Paris freaks out because Tristan is nowhere to be found. He finally shows up to tell Rory that his father has pulled him out of Chilton to send him to boarding school, because he was caught with Duncan and Bowman breaking into Bowman's father's safe on a lark. Paris storms off, puts on his costume, and takes over as Romeo, thereby saving the day, the performance, and their grades.