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The Simpsons (1989) - 3x16 - Bart The Lover

 
Plot Outline
During a particularly long detention jag, Bart discovers that his teacher, Mrs. Krabappel, has placed a personal ad looking for love. Thinking it would be funny to string her along, Bart writes her a love letter as "Woodrow," the perfect man who loves holding hands and hates yo-yos. Mrs. Krabappel falls madly in love with Woodrow and Bart begins to realize that he's done a very cruel thing. With the help of his family, Bart writes a sweet goodbye letter and lets his teacher gently off the hook.


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