Tired of being lonely, Mrs. Krabappel takes out a personal ad. When Bart smashes the classroom fishtank with his new yo-yo, she gives him one month's detention. Snooping through her desk for his confiscted yo-yo, Bart discovers Mrs. Krabappel's ad and comes up with a way to get back at her. He sends her a love letter and sign it "Woodrow." Mrs. Krabappel reads it and thinks she has finally found her true love. She sends her reponse with a sexy photo.

After writing back and forth and building a romance, Bart writes to Mrs. Krabappel, acknowledging it is time she and Woodrow meet. He sets up a time and place for the meeting. Mrs. Krabappel arrives at the appointed time, but the man of her dreams never shows.

Feeling bad, Bart tells his family what he has done. Marge suggests that Woodrow write another letter, letting her down easy and salvaging her remaining self-esteem. Marge, Homer, Bart, and Lisa compose a poetic masterpiece. When Mrs. Krabappel receives the letter, her spirits are lifted.