Plot

After Mrs. Krabappel gives Bart a month of detention, he gets his revenge by responding to her newspaper singles ad; Homer uses a swear jar to cut down on his cursing.

Lonely Enda Krabappel has punished Bart for one of his shenanigans again, so he decides to take revenge on her by responding to a personal ad, pretending to be a potential new boyfriend. Successfully stringing her along with corresponding love letters and setting her up for a date that goes bad, he starts to feel guilty over his actions and calls for help from his family to lift her spirits.—Daniel Timothy Dey

As a yo-yo craze sweeps through the elementary school when a group of four demonstrate the potential of the toys, Mrs.Krabappel feels increasingly isolated and places a personal ad in the newspaper. Bart breaks the class fish tank with his yo-yo, and is given one month of detention by Mrs. Krabappel. With his yo-yo confiscated from him, he plans revenge against her for what she did to him. Eventually, Bart discovers her personal ad, and decides to pull a prank and respond by mail with a new alter ego.

At the Simpson's Back Yard, Homer attempts to build a dog house for Santa's Little Helper, but each time he does, the lumber ends up collapsing. True to his nature, he ends up using profanity by cursing out a storm unaware that Todd heard him while he was playing. Later on at the Flanders house, Maude asks him if he would like to have some of her mixed vegetables. Todd's reply shocks his family when he says "Hell No!" and that he doesn't want any damn vegetables. Ned punishes him for swearing, but later decides against it because it wasn't really his son's fault. He decides to do an investigation to find out where his son learned the use of profanity from since he knows he can't do so. Apparently Todd hasn't been learning it from comic books, bumper stickers, T.V., and the rest of the Flanders family.

However, Ned's investigation leads to his next-door neighbor, Homer, when he's caught swearing again as he makes futile attempts to build a dog house for the family dog. This time, the board is stuck to his jacket due to the super glue and Flanders confronts him about his use of profanity in front of his boys, Rod and Todd. Homer tries to come up with both a critism and insult for Flanders in return, but the only thing he comes up with comes up with criticizing his moustache, which Ned promises to shave off in return for him curtailing uses of profanity. Homer agrees to it.

At Springfield Elementary: in Mrs.Krabappel's class, Bart pretends to be an adult male called Woodrow, named after former President Woodrow Wilson, with a photograph which actually belongs to ice hockey player Gordie Howe. Bart, as Woodrow, writes Mrs.Krabappel other letters, telling her what she wants to hear.

Later on in the Simpson's master bedroom, Homer gives Marge a story about Flanders complaining about his swearing being a negative influence on his boys. She tells him that she actually agrees with Ned because his cursing has been a problem for both the Flanders and their own family. Homer tells her that God made him the way he is and it's too late for him to sop cursing. Marge tells him it's not too late for him to stop cursing by relaying to him, a tale of her own father who had the same problem after he got out of the Navy. Mr.Bouvier almost lost his job as a baby photographer because of his constant cursing in front of his clientele and her mother solved the problem to his cursing. She set up a "swear jar" and each time her father started using profanity, he had to insert in a quarter($0.25) in the jar. Homer agrees to put money in a swear jar for each curse, for her sake. Before going to bed, he asked Marge a series of questions just to get the ground rules straight.

In the end, Homer resists temptations to curse but nevertheless experiences intense feelings of rage and his constant swearing:

• when he accidentally puts $20.00 in the church collection plate

• when he can't bowl a strike, rendering unable to get the last pin down

• when Flanders becomes a successful commercial actor after having shaved off his moustache.

• when he builds a doghouse with no door.

• when a beehive falls on him and his bee-stung hand contributes more money

That puts more than enough money in the swear jar to purchase a dog house for Santa's Little Helper with an added bonus, Duff Beer for Homer for at least commiting.

Bart then sends a letter asking for them to meet at the Gilded Truffle. He sees Mrs.Krabappel waiting for Woodrow, and then he goes to watch the movie "Ernest Needs a Kidney" and when he comes back sees Mrs.Krabappel still at the restaurant on the verge of tears. Bart is upset and guilty to see her crying. At the Simpson's living room, he confesses to the family what he had done to his teacher because he wanted revenge against her for his yo-yo being confiscated from him. Bart ends up being berated by Marge and Homer for his actions which were childish and unjust. Later on, the Simpsons decides to write a romantically diplomatic letter to to his teacher by telling her how Woodrow must go and his constant remembrance of her from the wind, which heals Krabappel's wounds.