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|Breaking Up Is Really, Really Hard To Do|
|Original Airdate||January 27, 1995|
|Written by|| Mark Blutman|
|Directed by||Jeff McCracken|
|Guest starring||Katy Barnhill as Lori, Katie Johnston as Bonnie, Jason Marsden as Jason Marsden, Musetta Vander as Dominique, Jessica Wesson as Wendy|
Cory has a problem: he has been invited to a couples only party. Calling once more on his dating guru friend, Shawn, for advice, he asks Wendy to be his girlfriend. In reality, he only wanted to have a date to the party, but he lies, telling her that he feels they are ready for a relationship. Wendy is enamored, and she immediately accepts Cory as her boyfriend. From there, everything spirals out of Cory's control.
While Cory only wanted a date to the party, Wendy was looking for a lifelong relationship, and immediately immerses herself in Cory's life, starting to plan marriage and beyond. Cory puts up with it at first, sure that it's just a phase. Shawn thinks so, too, and after a week of their relationship, he advises Cory to break up with Wendy, telling him that she's probably getting bored with the relationship, as well. Cory agrees and writes a breakup note, which he passes to Wendy in class after she gives him socks. Mr. Turner reads Shawn's poem first, which talks about his various family members on welfare. Mr. Turner is perturbed, and moves on to Wendy's poem. As he begins to read the poem, which clearly talks about her love for Cory, Cory's conscience kicks in, and he asks for the note back. However, Wendy reads the note and excuses herself from class, followed closely by Cory, who states that he did not want to break up. They hug, but when Wendy talks about future kids, he is put off again.
She leaves, and he goes into a dream sequence, in which he has been married to Wendy for 90 years. The relationship was smooth, but Cory was clearly unhappy. He is awakened by Mr. Feeny, who appears the same age in the dream.
Later that night, he finds that Wendy is in his kitchen, and the women in the family have taken to her. Alan and Cory are plainly perturbed, but Morgan and Amy see nothing wrong with her. Amy continues to believe that Wendy is just playing house until she brings down a photo of Amy in her wedding dress, telling her that she hopes that she gets to try it on one day. This finally convinces Amy that Wendy is moving too fast, and Cory resolves to take action at Chubbie's. Wendy continues to talk about the future, but when Cory tells her the truth, she breaks up with him. Shawn congratulates him and invites him to a party, but Cory says he isn't interested, and lifting up his feet, still wearing the socks Wendy gave him, says that he misses her.
Meanwhile, Eric is banned from dating until he gets his grades up. Jason takes him to a hair salon to meet Dominique, claiming that a haircut from a woman is a parentally acceptable dating substitute. Eric isn't interested at first, but once he gets there, he finds her attractive. They continue a pseudo-relationship until the end of the episode.