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S03E16 Bart the Lover

Original air date February 13, 1992
Season 3
Episode 16

Springfield Elementary School teacher Edna Krabappel, feeling increasingly lonely and isolated due to the lack of a male presence in her life, places a personal ad in the newspaper. During a detention session where Edna is not present, Bart rummages through her desk and discovers her personal ad, ultimately deciding to respond to it as a prank.

Bart sends Edna a romantic letter using the alias Woodrow. Using dialogue from old romance films as well as Homer's old love letters to Marge, Bart tells Edna what she wants to hear, increasing her romantic interest in Woodrow. When Edna asks to meet Woodrow for dinner so they can finally meet, Bart, intending to end the prank, responds by asking her to meet with him at the Gilded Truffle restaurant. Unwilling to keep the date, Bart goes to a cinema to see a movie. On his way there, Bart sees Edna waiting for Woodrow and laughs. When the film ends, Bart returns to the restaurant and feels regretful when he sees Edna crying at her table.

Bart feels worse after being unable to console Edna. Not knowing what to do, he finally tells his family about his prank letters. Lisa suggests "Woodrow" write her a goodbye letter, and the family agrees to do so. Together, they collaborate on a romantic letter for Edna, with "Woodrow" announcing that he must leave but will never forget Edna. Edna feels better after reading it and invites Bart to spend his last day of detention outside the classroom.

In the subplot, Marge notices that Santa's Little Helper needs a new dog house. Homer tries to save money by building one himself, but his attempts fail and he curses loudly enough for Todd Flanders to overhear and repeat them at dinner. Ned complains to Homer, who criticizes his mustache. Ned promises to shave it off if Homer stops swearing. Marge suggests he put twenty-five cents for each curse in a swear jar (as her father used the same technique to cure his swearing problem as well). Homer's constant swearing eventually puts enough money in the jar to buy a dog house and a six-pack of beer.

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