Amidst her sadness about Christopher, Lorelai has an intriguing dream about Luke; Rory returns from Washington to realize that she still may have feelings for Jess, but a chance encounter at the First Annual Stars Hollow End of Summer Madness Festival makes her realize that he may have moved on to someone else; relationship quarrels abound -- Sookie and Jackson over decorating their house, Lorelai and Rory over Jess versus Dean, Emily and Richard over Lorelai and Christopher -- but are on the path to resolution; and Rory once again guides Paris through the rocky shoals of preparing for a date.

To Lorelai's horror, Kirk asks her out on a date after being encouraged by Luke; Emily's lunch with Lorelai at Luke's ends badly; Christopher shows up uninvited at Friday night dinner and quarrels with both Lorelai and Rory before Emily asks him to leave; Rory runs into Jess and they each betray their hurt feelings -- Rory about Shane and Jess about not hearing from Rory all summer; and Francie targets Paris and Rory for a world of trouble if Rory doesn't stop Paris from running the student council like a dictatorship.

Lorelai's stint in the Stars Hollow High School local business success speakers forum gets derailed by some controversial personal questions, much to the delight of Luke and the consternation of some PTA mothers; Luke and Jess argue about the women in and out of their lives (and their closets); Lane alleviates her frustration about the strictures of her household and the future of her band through a colorful, if temporary, display of independence; Rory runs into Shane one too many times and succumbs to a severe bout of snarkiness.

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.