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Woodrow was an alias that Bart Simpson invented as a prank to respond to a personals ad placed by his teacher, Edna Krabappel.

Mrs. Krabappel had given Bart a month's detention and taken away his yo-yo because of a yo-yo stunt that had killed the classroom fish. Bart was angry about it and looking for opportunities for revenge. When Mrs. Krabappel stepped out of the classroom during one of his detentions, he rummaged through her desk and found his yo-yo (which he took back) and a personals ad that she had placed.

Bart decided to get revenge by sending a prank reply to the ad. He started by saying that he liked holding hands and dinner by candlelight. Also, because he knew that Mrs. Krabappel was annoyed by the yo-yo craze that had swept through Springfield Elementary School, he added that he hated yo-yos in order to further appeal to her. Finally, he needed a name to sign to his reply, and decided on "Woodrow" after he looked around and spotted a portrait of former U.S. President Woodrow Wilson. The letter was a total success as Mrs. Krabappel immediately fell in love with Woodrow when she got the letter.