After Bart successfully escapes the house with Homer's loose change, which is set up to act as a satire of Raiders of the Lost Ark, Bart sits down with Milhouse, who shows him his Magic 8-Ball that he bought from the Circus of Values. After it is tested, Bart is convinced it is capable of predicting the future. He proceeds to ask another question: how long he and Milhouse will be friends. But no matter how low Bart sets his sights, the ball denies that their friendship will last long. Bart is curious what could possibly come between their friendship... and we see a potential threat in the form of a new female student at Springfield Elementary named Samantha Stanky.
While Bart proves to everyone that Milhouse's Magic 8-Ball was correct in predicting the future, he previously asked if he would pass his English test, and he didn't, Principal Skinner introduces Samantha to the After Samantha tells the a little about herself, during recess Milhouse is temporarily blinded by a dodgeball and he discovers Samantha admirably smiling at him.
Back in Mrs. Krabappel shows the a sex-education film narrated by Troy McClure called "Fuzzy Bunny's Guide to You-Know-What." While Bart finds the film boring, Milhouse and Samantha catch each other's eyes. In Bart's treehouse, Milhouse joins him and then reveals that he's brought Samantha with him. At first, this doesn't please Bart, but he relents saying she can read comics with them. Bart goes to collect Lisa's collection of more girl-oriented comics, but is shocked to discover Milhouse and Samantha kissing in the treehouse.
At night, while Homer and Lisa are watching "Smartline", Kent Brockman does a report on how many American people are obese. Lisa then has a dream in which her father dies from being grossly overweight and resolves to help him. She offers to ask him if he'd like to lose weight without exercising and Homer is left thinking a deal in the Eternity magazine is a great idea. Marge tells Homer that she loves him as he is, but asks Lisa for the number and calls for the weight loss tape. However, they are out of subliminal weight loss tapes and Homer gets a vocabulary-building tape instead. Homer's appetite does not get curbed; but now he has started using much more syllabic words than before and he is getting harder to understand.
As Milhouse continues to care more about kissing Samantha then being friends with Bart, Bart starts to look elsewhere. He tries Martin, but their new friendship doesn't last too long and he returns to Milhouse. After they see the newest Space Mutants movie, Milhouse tells Bart that there is such a thing as spending too much together and Bart says this is fine as he can't stand their "lip wrestling" anymore. He leaves, but Milhouse catches up with him and asks if they can still use his treehouse. He explains his plight; if her strict father learned about what she has been doing, it would spell the end of their relationship. Bart says it is okay, but afterwards laughs evilly.
Bart goes to call Mr. Stanky, who then appears at the treehouse catching his daughter in her act. He takes Samantha away and tells her he will put her in an all-girl school where she will never see Milhouse again. Milhouse breaks down.
In the meantime, Homer learns he's gained weight and is fed up with the tape, convinced that it's not working.
Bart goes to ask Lisa for advice while Marge is not home, (and he couldn't understand what Homer was saying) telling her he feels bad about ratting out Samantha. Lisa tells Bart a new formula is under development that is supposed to eliminate guilt, but it won't be available for half a year so she tells him all he can do is confess.
Bart goes to see Milhouse, who is still crying over having lost Samantha. Once Bart tells Milhouse that he is responsible for squealing to Samantha's father, Milhouse attacks him. While Milhouse has Bart in a strangle hold, Bart tries to grab a weapon to escape. He grabs Milhouse's Magic 8-Ball and decks him with it, causing the ball to break.
While Homer's vocabulary returns to its original state, Bart and Milhouse go to "Saint Sebastian's School for Wicked Girls" to see Samantha. Milhouse sees her, and gives her a bucket of Gummy Bears. Bart apologizes for getting her sent to this school, but Samantha tells them she loves Saint Sebastian's. Once the bell rings, Samantha tells them she must go to Milhouse puckers up, but Samantha tells him she will be punished if she kisses someone. But she gives in, kisses Milhouse and leaves. Milhouse asks Bart if he can ever find another girl like Samantha, but Bart tells him that he's the wrong person to ask; they all look alike to him. In the meantime, he suggests that they go have fun.
Finally, we see a quick shot of a flashcard consisting of Professor Homer giving a lesson to "Increase Your Wordness."