It's the first day of a school and Cory has been waiting all summer to ask Topanga to be his girlfriend. He's got new clothes, new cologne and a new attitude; that is, until he actually gets to school. Topanga, who went away for the summer, is more beautiful than he remembers and he freezes when he tries to ask her out. When he finally gets up the nerve at lunch, she tells him that she has plans with someone else. Dejected and seeking solace, Cory turns to Shawn; but when Shawn reveals that he was the one who asked Topanga out, Cory feels defeated and alone.
Meanwhile, in an effort to garner extra-curricular activities for his college resume, Eric takes over as promoter for the Film Society. He has one problem though; no one wants to see "Paint Your Wagon". He's about to give up when Frankie and Joey step in and offer their services. "We'll take all the tickets and we'll sell the show out for you," Joey promises, in exchange for a piece of the profits.
Back at Mr. Turner's apartment, Shawn is lounging on the couch when Cory barges in, demanding an explanation. Shawn insists that he did nothing wrong because Cory didn't move quickly enough. Cory leaves in a huff wondering what's going to happen next.
At home Eric suggests that Cory ask Topanga's best friend, Trini, about the situation. Cory thinks this is a good idea and goes to lunch with her at Chubbie's. Trini misinterprets his intentions and thinks he is asking her out. When Cory sees Shawn walk in with Topanga, he decides to ask with Trini to the Film Society screening.
Thanks to Frankie and Joey, the film is sold out. The only thing they had to do was change the film from "Paint Your Wagon" to "Texas Gutsuckers Part 5: Leon's Revenge". Topanga, Shawn, Cory and Trini all sit together at the screening. They make themselves cozy until Mr. Feeny shows up and busts Eric for switching films. With everybody gone, Cory express his frustration and true feelings for Topanga. He asks her to be his girlfriend and she kisses him, yes. At that moment, Shawn and Trini walk in and reveal that it was all part of Shawn's plan to get Cory to build up the nerve to ask Topanga out.