When Shawn's girlfriend, Jennifer, dumps him, Cory tries to cheer him up by pointing out her flaws. When Jennifer expresses interest in reuniting with Shawn, he tells her everything Cory said. This angers Jennifer, who uses her feminine wiles to forbid Shawn from seeing Cory.
The boys secretely speak on the phone and agree to meet each other at the library in the morning. Jennifer shows up at the library putting a damper on this plan, but Topanga manages to get Shawn over to some bookshelves where Cory is waiting on the other side. They try to figure out how to meet next, but Jennifer comes over to the shelves, forcing Cory to hide.
At home, Cory prepares an elaborate dinner for Shawn, but Shawn calls from a country club and says he has to cancel because he can't get away from Jennifer. Topanga witnesses Cory's side of the sad conversation and tells Cory that a best friend is part of who a person is, and nobody can replace that relationship. Cory realizes that Shawn deserves to go out with a girl who understands this. Topanga goes to leave, but tells Cory to meet her at Chubbie's in an hour.
An hour later, Shawn arrives at Chubbies and meets Cory and Topanga. Topanga leaves the boys alone so they can talk and play pool. Everything seems to be going well until Jennifer walks in, saying she got an anonymous tip on her cell phone. Topanga reveals that she made the call because she thought that it'd be better if everything was just out in the open. Jennifer gives Shawn an ultimatum: Cory or her. Shawn tells her that if she can't be friends with his friends, then he doesn't want to be friends with her. She dumps him, but it doesn't bother him this time. "I know I'm gaining more than I'm losing."
Meanwhile, Eric finds out that his parents spent 60 dollars for a pair of tickets to see a one-woman show, and decides to write his own one-man show. He puts in a lot of effort and fills 400 pages with self-indulgence. "Eric Matthews: Look At Me, Look At Me", bombs, and a disheartened Eric thinks that his life isn't interesting. Mr. Feeny tells him that in the play of his life, all his great scenes lie ahead of him.