When Bart discovers that his divorced teacher, Mrs. Krabappel, has placed a “personals” ad in the local newspaper, he decides to create fake correspondence.
Tired of living a lonely, unfulfilled existence, Mrs. Krabappel takes out an ad in the personals. In the school auditorium, Principal Skinner introduces the “Twirl King Yo-Yo Champions” to the children. When Bart tries to do a trick with his new yo-yo, he smashes the fish tank. Mrs. Krabappel takes away his yo-yo and makes Bart serve detention after school. The men who respond to Mrs. Krabappel’s ad are unacceptable, so she resigns herself to living the life of a spinster. Snooping through her desk, Bart discovers Mrs. Krabappel’s ad. After reading it, Bart gets an idea how to get her back for impounding his yo-yo. Bart sends Mrs. Krabappel a love letter and signs it Woodrow. When she reads it, she thinks she has finally found her one true love.
Homer decides to build Santa’s Little Helper a dog house. But his little project turns into a major calamity. Hearing Homer swearing in his backyard, Ned Flanders agrees to shave off his moustache if Homer curbs his foul tongue. Marge tells Homer that every time he says a profanity, he has to put a quarter in the “swear jar.” Bart writes a letter to Mrs. Krabappel telling her it is time her and Woodrow met, sending a picture of Gordy Howe. He sets up a time and place. Mrs. Krabappel arrives for their rendezvous, but the man of her dreams never shows.
Mrs. Krabappel is crushed. Feeling bad, Bart tells his family what he has done. To avoid hurting Mrs. Krabappel with the truth, Marge suggests Woodrow write her another letter, letting her down easy and salvaging any self esteem she may have left. Marge, Homer, Bart and Lisa all pitch in to compose a poetic masterpiece. When Mrs. Krabappel receives it her spirits are lifted, feeling it is better to have loved and lost, than to have never loved at all.
Source: 20th Century Fox