After a group of professional yo-yo-ists come to Springfield Elementary, everyone starts playing with yo-yos. Bart becomes a great yo-yo-ist, however, for one trick he hits the fish tank with his yo-yo and breaks it. Mrs. Krabappel gives him an after school detention.
While cleaning the room he goes through Mrs. Krabappel's desk and finds a want ad for a man. Bart answers it in the name of "Woodrow" and soon they are both writing back and forth. She asks "Woodrow" for dinner, so Bart agrees, leaving her alone in the restaurant.
Bart feels sad so he reveals it to the family. They then write another letter as Woodrow saying that he must leave her forever. Bart leaves it on her doorstep, making Mrs. Krabappel happy again.