Through the years, ''TheSimpsons'' became well known for stories not just on the title family, but insightful, thoughtful episodes on the residents of Springfield. One of the better early examples was Edna Krabappel, the fourth-grade teacher at Springfield Elementary who despite her marginal skills sometimes is dedicated to her profession, even when she's on the verge of being burned out.

Here, we learn that Mrs. Krabappel hasn't had a man in her life since her husband divorced her. She's lonely and it is something that an angry Bart hopes to exploit when he becomes "'''Bart, the Lover'''."

Bart had played the latest in a series of classroom pranks, and this time one of his jokes goes too far ... he damages the classroom aquarium, causing a big mess and killing all the fish. Mrs. Krabappel decides to hold him in detention for a week as a consequence. Bart, of course, balks and insists he did nothing ''that'' wrong ... and isn't going to take this matter lying down.

Bart decides to get his revenge by exploiting Mrs. Krabappel's increasingly loneliness and desire for companionship ... by sending her love notes from a man named "Woodrow." She takes the bait she sees hope that "Woodrow" is the man she had been seeking all along, and asks to go out on a date.

Edna meticulously prepares for the date at a fine restaurant, and Bart out for a walk cackles evily as he sees her go inside. However, when he returns later to the restaurant, "Woodrow" has never showed, and Edna unaware that Woodrow doesn't exist is near tears. Only then does Bart feel remorse, and he admits his prank to his parents. Marge fearing the truth would hurt her more than forcing Bart to confess and accept what surely would be severe consequences has Bart write a farewell note from "Woodrow."

In the subplot, Homer cusses up a storm outside his home, and an impressionable 7-year-old Todd picks up on it. One evening at dinner, he begins repeating the language, prompting Ned to send him to his room. Ned tries to find out the cause, but eventually overhears Homer swearing in frustration over his shoddy workmanship skills (Homer was trying to build a doghouse for Santa's Little Helper). Ned asks him to tone down the language, and Marge overhearing the conversation agrees. The result is a "swear jar," which Homer, every time he's caught using profanity, has to contribute to. Eventually, Homer is cured of his foul mouth and realizes he has enough to buy a well-built doghouse ... and he then takes his frustrations out on the "alleged" doghouse he tried to build.

* {{Bizarrchitecture}}: Homer's "attempts" to build a doghouse.
* CurseCutShort: Several from Homer ("Da-", "You sunofa-", "You dirty bast-," and "Aw...").
* EpicFail: Homer building a dog house with no door to it. While it ''is'' physically possible to do something like that, the fact that Homer did shows the depth of his ineptitude.
* FacePalm: Reverend Lovejoy has a glorious facepalm when his wife informs him that Ned Flanders is on the phone. Lovejoy would prefer to enjoy his dessert in peace and not to deal with Ned's latest "crisis."
* GoshDangItToHeck: An epic one from Homer, when he's mentally conditioned not to swear.
--> '''Homer:''' [[TranquilFury -hammers thumb- Oh fudge, that's broken.]] [[MajorInjuryUnderReaction -steps on nail- Fiddle-Dee-Dee, that will require a tetanus shot.]] [[ExactWords I'm not going to swear,]] [[RageBreakingPoint but I am gonna]] [[SuddenlyShouting KICK THIS DOG HOUSE DOWN!!!]] -proceeds to do so.-
* HilariousInHindsight: Mrs. Krabappel's line about not wanting to date Principal Skinner because "...his mommy won't let him out to play," is funnier after watching the season eight episode "Grade School Confidential" (where Skinner and Krabappel do date), but HarsherInHindsight as of "My Big Fat Geek Wedding" because of their break-up (and harsher still when, prior to Marcia Wallace's death, Mrs. Krabappel married Ned Flanders).
** Mrs. Krabappel's line about Groundskeeper Willie being into something sexually deviant ("Yech! I'm not even gonna tell you what that guy's into) is funnier after watching "Homer Badman," where it's revealed that Groundskeeper Willie is a Peeping Tom who likes to videotape people having sex in their cars (and in "Thirty Minutes Over Tokyo," he has an upkilt website and in "Bye Bye Nerdie," he put video cameras in the school to assuage his fetish rather than because the school needs extra security measures).
* LoveLetter: Bart and Edna write several love letters to each other. Bart asks for tips from his whole family, and Marge shows Bart a love postcard she got once from Homer.
* SwearJar: Marge makes Homer put money in it for foul language because one of the Flanders little boys picked it from him.
* TheStinger: The episode ends with a trading card-style rundown of the hockey career of Gordie Howe, Woodrow's face.
* TwoWordsObviousTrope: Homer's suggestion for a break-up letter for Mrs. Krabappel is "Three little words: I am gay."