- Bart gets Milhouse to take the rap for a prank at school, and then blows him off when he falls for a cute 5th grade do-gooder, prompting Milhouse's wrath. Meanwhile, Lisa begins taking "happy pills" to improve her negative outlook.
- Milhouse and Bart loosen every bolt and screw in Springfield Elementary, leading to mass chaos when the building and its contents fall apart. Milhouse is apprehended by Principal Skinner and suspended from school for a week. Bart, whose involvement with the prank was not discovered, feels guilty for what happened and promises to visit Milhouse every day. For the first few days, he keeps true to his word to Milhouse and visits him during his suspension. Milhouse admits the only downside to being suspended is having to hear his dad scream out at the television for every wrong answer the contestants give out on the game show. Homer drops Bart off at Springfield Retirement Castle to visit Grandpa. There, he is immediately smitten with a kind and charitable 5th grade girl named Jenny. Bart makes a concerted, but heartfelt effort to appear "good" to her, demonstrating his newfound good nature by defending ducklings and eventually inviting Jenny over for supper.
Meanwhile, Lisa is assigned to write a report on what Springfield will look like in 50 years. When she learns about the soon-to-be famine of the future, she becomes depressed and terrifies her classmates with her dark visions of their future. Homer and Marge take her to a psychiatrist, who prescribes Lisa "happy pills" known as "Ignorital". She is initially skeptical, but after taking her first pill, she loses touch with reality and sees the entire world as smiley faces (all to the tune of Louis Armstrong's What a Wonderful World). Soon after she forgets her depression.
During dinner, Milhouse shows up on the Simpson's doorstep, angry and wet at Bart. Just before he could explain himself to his friend, Jenny comes to the door, asking him what's wrong. Milhouse is quickly infuriated with Bart for neglecting to visit him during his suspension and threatens to reveal his friend's true, dark nature to her should he continue ignoring him.
In Lisa's room, she is in a drug-induced stupor having lost all touch with reality. She nearly kisses a running fan held by Maggie, until Marge showsa up to take the fan from her infant daughter. She decides that Lisa's had enough of the pills and should not take them anymore. She tosses them in the waste basket, where they are promptly eaten by Santa's Little Helper, who nearly kisses the fan himself.
True to his threat, Milhouse begins appearing on Bart and Jenny's outings, each time hinting at Bart's misdeeds. At the Springfield Squidport fair, he shows up and even made the dolphin confess to Bart's dark nature by admitting that he made the poor dolphin drink his spilled soda in the tank. When Jenny asks Bart if what his friend is hinting is true about him. Eventually, Bart sees there is no way out of his predicament since Milhouse sealed all the exits off, he confesses to Jenny that he was actually bad before he met her and only pretended to be good to start a relationship. He continues to say that he is changed completely because of being with her, yet Jenny is furious and leaves him, pleasing Milhouse.
Heartbroken, Bart is at the Kwik-E-Mart, drowning his sorrows on a couple of Skwishees(think 7-11 Slurpees). Soon, a back to normal, Lisa shows up and wisely tells him that he should try to deal with his heartbreak by apologizing to Milhouse for neglecting to visit him during his last few days of suspension. She relates a story of her own about her own problems with her depression for the future of the world. After taking Ignorital, she lost sense of her reality and kept seeing happy faces everywhere she went. In her drugged-stupor, she almost kissed her fan until Marge intervened and threw her pills away. Bart decides to take Lisa's advice, buy a bouquet of roses, and apologizes to Jenny for lying to her about his true character and Milhouse for his neglect to visit him.
In the end, it is revealed that the apology and roses are for Milhouse. The two friends reconcile and play a prank together, repeatedly driving a Zamboni over the floor of the school until it is as slippery as ice. Once class is over, the kids are slipping around the ice having a good time. Skinner, on the other hand, is infurated with Bart, while Chalmers screams Skinner's name.
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