Synopsis by Mark Deming
After a team of professional yo-yo tricksters makes an appearance at Springfield Elementary School, the toy enjoys a massive resurgence of popularity among the students, and as one might expect, Bart Simpson (voice of Nancy Cartwright) goes a bit too far, destroying the fish tank in his classroom while showing off a trick. Bart's teacher Mrs. Krabappel (voice of Marcia Wallace) punishes him with a month of detention, but as he rummages through her desk one afternoon while she's stepped out for a cigarette, Bart discovers his teacher's love life has gotten so grim that she's placed a personal ad in a local newspaper. Hoping to play a prank on her, Bart answers the ad, claiming to be a man named Woodrow who enjoys candlelight dinners and loathes yo-yos. After Mrs. Krabappel responds by sending "Woodrow" a photo of herself in a negligé, Bart sends her a snapshot of "Woodrow" -- an old picture of hockey legend Gordie Howe. Bart has a grand time fabricating this phony romance, but when "Woodrow" stands up Mrs. Krabappel after what was supposed to be their first date, he realizes just how lonely she is -- and how much his prank has hurt her. "Bart the Lover" first aired on the day before Valentine's Day in 1992.