Lorelai is determined to win the Stars Hollow Dance Marathon and wrest the trophy from four-time champion Kirk, but has trouble getting a partner until she finally convinces Rory to help her dance her way to victory. Dean sits on the sidelines to cheer his girl on, and is soon joined by Jess and Shane, who spend their time making out while Jess keeps his eye on Rory. Lorelai breaks her heel, and Dean takes her place while Luke plays shoe repairman. On the dance floor, Dean realizes that Rory is attracted to Jess and breaks up with her. Rory tearfully runs off, followed closely by Jess, and Kirk is declared the winner once again.

In the aftermath of the Dance Marathon, Kirk parades around Stars Hollow with the trophy until someone steals it, while Lorelai and Rory painfully inch their way towards Luke’s; after Lorelai tells Luke about Rory and Jess, he breaks up their first kiss as a couple and then lays down some ground rules with Jess about dating Rory; Lorelai and Rory reluctantly agree to accept Richard’s invitation to accompany him and Emily to his Whiffenpoof reunion at Yale, where he springs quite an unwelcome surprise on all three women; back from New Haven, Lorelai and Rory head for Luke’s, and Jess and Rory finally get to have those first kisses; Rory visits Dean to apologize and tell him that she misses his friendship; late at night, Lorelai and Rory each curl up with some bedtime reading — the Yale brochure.

It’s Thanksgiving, and Lorelai and Rory have dinner at four different places: the Kim’s, where Lane has managed to get Dave invited and Lorelai is forced to eat tofurkey; Luke’s, where Luke and Jess make it a foursome with Lorelai and Rory; Sookie’s, where Jackson and his family have deep-fried the turkey, the lawn and just about everything else; and Emily and Richard’s, where, to Lorelai’s horror, Rory reveals that she has applied to Yale. Kirk gets a cat, with disastrous results; Dave asks Lane out, and then kisses her; Paris is afraid her difficulty getting into a shelter will impact her acceptance to Harvard; and Dean faces off with Jess and lets him know that it’s no more Mr. Nice Guy for Mr. Forester.

Lorelai’s grandmother arrives in Hartford unexpectedly on Richard’s birthday and announces that she’s moving back, throwing Emily into a tizzy until she follows Lorelai’s advice on how to manage her mother-in-law; Rory declares war on Francie after she pulls a runaround on Paris with the Student Council; Paris finds herself in love after spending Christmas vacation with Jamie’s family; after Rory and Dean bump into each other a few times, they decide to be friends again; Jess initially declines Rory’s offer to attend the Stars Hollow High Winter Carnival, but changes his mind after they run into Dean and his sister Clara, who invites Rory to join them; Jess gets Dean alone at the carnival and lets him know that he’s wise to his plans to get Rory back.