After a close encounter (Indiana Jones style Indiana Bart), Bart Simpson manages to retrieve Homer's jar of change to take to school. His best friend, Milhouse, in the meantime, has chosen to take his Magic 8 ball. Bart asks the ball whether he and Milhouse will still be friends by the end of the day, and the ball predicts no. Both are puzzled by how this could happen.
A new girl from Phoenix, Arizona, called Samantha Stanky starts at Springfield Elementary School and Milhouse falls in love with her. She also starts falling for him. To Bart's dismay and anger, Milhouse and Samantha start a relationship and, rather than playing with Bart after school in his treehouse, Milhouse brings Samantha with him and spends the entire time kissing her. They ignore Bart, leaving nothing for him to do but leave. Marge finds this incredibly sweet (although she hopes they are not "opening their mouths, are they?"). In order to restore the previous status quo, Bart calls Samantha's father and lets him know what's happening, and Mr. Stanky rushes to Bart's treehouse and takes her away before she can even explain. She is sent to St. Sebastian's school for Wicked Girls, an all-girls convent school. Bart lets Milhouse know that he told on him and Samantha and they fight over Bart's actions. Milhouse visits Samantha at the convent school and Bart apologizes to her, but she say it is OK - she loves Saint Sebastian's. However, she still has feelings for Milhouse and gives him a goodbye kiss, despite her knowingly violating school rules.
Meanwhile, Lisa is watching a documentary on the health problems of obesity. She is fearful that Homer's obesity will lead to an early death. On Lisa's suggestion, Marge orders a subliminal weight-loss tape for Homer. Humorously enough, the company is out of the tapes and sends Homer a "Vocabulary Builder" tape. Homer ends up eating more than ever, but his vocabulary is through the roof. However when he realises that the tape does not work he gets rid of it and his vocabulary quickly returns to normal (or maybe worse than that).