Luke's sister Liz, afraid that her 17 year old son Jess is headed for trouble, puts him on a bus to Stars Hollow to live with Luke. Lorelai finds out and offers Luke some guidance on the care and feeding of a teenager, but is rebuffed. Undaunted, she hosts a dinner party for Jess, who is sullen and angry with everyone except Rory. At the first opportunity, he takes a beer from the fridge and sneaks out to the back porch. Lorelai finds him and gives him a lecture on how good he has it with Luke. Jess tells her what she can do with her little speech and then leaves. When Luke finds out about Lorelai's meddling, they quarrel and he goes to find Jess. Taylor calls Luke the next day to accuse Jess of stealing money from the bridge fund container at the market. Luke confronts Jess about this accusation, and becomes so frustrated at his response that he shoves him into the lake. Realizing that he needs Lorelai's help, he goes to her house to patch things up, only to find that one of Babette's gnomes is missing. He goes back to the diner, lays down the law to Jess and retrieves Babette's gnome. Paris is intent on making Rory's life miserable, so she sabotages her participation on "The Franklin" by giving Rory the wrong time for the staff meeting, and then assigning her to a story on the paving of the new faculty parking lot. Her plan is frustrated when the faculty advisor singles out Rory's article for praise. Undeterred, Paris assigns Rory the job of interviewing Max after she sees Rory and Max painfully avoid each other in the hall. Rory accepts the challenge, and after a few painful moments, Max and Rory express their regrets to each other about not being able to be stepfather and stepdaughter.

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.