Mrs. Krabappel's new pen pal has the name of the 28th president, the face of Gordie Howe, and the lines of a food-obsessed Frenchman. Is he the perfect lover, or Bart's latest practical joke? Meanwhile, Homer starts building a doghouse, and learns to give up swearing.
A yo-yo craze sweeps through Springfield Elementary School, much to Edna Krabappel's annoyance. At the same time, she is feeling increasingly lonely and places a personal ad in the newspaper, ending with "Object: SAVE ME." Bart, who has been given one month of detention for breaking the classroom fish tank with a yo-yo, discovers the ad and, realizing it is Mrs. Krabappel's, decides to pull a prank and respond by mail with a new alter-ego. Bart pretends to be an adult male called "Woodrow," named after former President Woodrow Wilson. For romantic writing to send to Edna, Bart borrows a couple of lines from Homer's old love letters to Marge. A chain of romantic correspondence follows, where Edna sends Woodrow a sexy photo of herself and Bart reciprocates by sending her a picture of ice hockey player Gordie Howe, claiming that it's a photo of Woodrow.
Edna takes the next step, asking if she and Woodrow can meet in person, have dinner, and return to her apartment for some "home cookin.'" Bart, as Woodrow, writes a letter making a date to meet at The Gilded Truffle for dinner, and Edna is excited at the prospect of meeting Woodrow. Bart, however, has no intention of keeping the date, and while Edna waits in vain for Woodrow at The Gilded Truffle, Bart goes to the movies. Later, he comes out of the movie theatre, laughing after watching "Ernest Needs a Kidney," and then is upset and guilty when he sees Edna crying while sitting at a table by herself. At school, Bart tries to cheer her up saying she can date the men in the school. However, Edna point out their flaws like how Skinner still lives with his mother, and the gym teacher drinks a lot. Remorseful, Bart tells the family what he has done, and Marge tells him, "You did a very cruel thing." Homer said Bart should tell the truth to Edna, but Marge said that the truth would humilated her. Lisa suggests they write a letter to tell Edna goodbye without hurting her feelings, and after several attempts they produce a romantically diplomatic letter where Woodrow says he must go, but will always remember Edna. Homer repeatedly pitches the same idea: "I am gay." However, he helps the family create an acceptable letter. The letter is a success: Edna is left feeling sorry that Woodrow is gone, but happy with how things ended.
Meanwhile, Homer attempts to cut down on his cursing after receiving a complaint from Ned Flanders about Todd picking up profanity by overhearing Homer. Homer tries to criticize Flanders in return, but can't find anything to criticize him for except his moustache, which Ned promises to shave off in return for Homer's cutting back on the swearing. Homer begins putting money in a "swear jar" -- 25 cents for each curse—and Homer's constant cursing rapidly fills the jar, although he does gradually curse less and less. Eventually, Homer becomes frustrated while building a doghouse. Combined with seeing a clean-shaven Ned thank Homer because his beardless look enabled him to star in a TV commercial, Homer loses his cool, and kicks the doghouse to pieces—but manages to avoid swearing. Marge and Lisa then surprise Homer with a brand new doghouse, easily bought and paid for with the money from the swear jar.