Bart and Lisa are playing Cowboys and Indians with their friends, until their game is interrupted by their parents, who want them to go to church, among other activities. In church, Bart is bored and is not listening to Reverend Lovejoy's sermon. Lovejoy's daughter, Jessica Lovejoy, reads the very same sermon. Seeing her, Bart is delighted by her, thinking his search for a girl is finally over. However, when he approaches her, she ignores him. The next Sunday, Bart decides to be in Sunday school, and tries to be nice to her. Again, she ignores him. Frustrated, Bart goes to the park to play a prank on Groundskeeper Willie at the Scotchtoberfest, which turns out to be a setup by Principal Skinner. Bart is punished with three months of detention, while Willie is angry at Skinner for using him. Jessica then asks Bart to dinner with her family, which he accepts. When Jessica leaves, Bart says, "There's only one thing to do at a time like this: strut!" and he struts down the street while "Stayin' Alive" plays.
At the Lovejoy house, Bart is kicked out for allegedly swearing after Rev. Lovejoy hears him say the word "butt." Jessica instantly sees Bart as a bad boy, and she finds him very interesting. He sees Jessica as being "smart, beautiful, and a liar". They go out on the town, vandalizing landmarks and having the time of their lives. Bart, however, develops a problem with seeing her, realizing that Jessica is more of a troublemaker than him. Lisa suggests that Bart not see Jessica for three months. He agrees, but when he goes to church, he sits next to Jessica, who steals the money from the church collection plate, and puts the plate in Bart's lap. The congregation declares Bart the perpetrator of the theft, and indicts him as a thief and a crook. However, Chief Wiggum cannot officially charge or arrest Bart due to lack of evidence. At home, Homer tells Bart that he'll believe him if he can look him in the eye and say that he didn't steal the collection. When Bart does this, Homer strangles him, "How could you look me in the eye and lie like that?!" Marge tells Homer that her son is innocent. Homer doesn't believe him, as Bart wore 'fancy clothes' to church. Bart fails to get Jessica to turn herself in and she reminds him that because she is the Reverend's daughter nobody would believe his story. However, Bart reveals the truth to Lisa, who vows not to let him take the blame for this. When Bart dreamily remarks that Jessica's hair smells like red Froot Loops, Lisa threateningly says, "Yeah? Well, I eat Froot Loops for breakfast."
The next week in church, Lisa tells the congregation that they should not indict Bart without evidence, and she wants all people considering themselves guilty to confess to a bad thing they did. She waits for the real culprit to come forward, but Jessica stays silent. Lisa then rats her out and suggests the congregation search Jessica's room. The money is found hidden under Jessica's bed, having everyone to realize that she did it all along and not Bart. Even though everyone's convinced about the truth, Reverend Lovejoy still refuses to admit to the evidence by telling that Bart moved his room to their house in order to save his daughter, but Jessica admits that she did it, to gain attention from her father. Reverend Lovejoy blocks her out by singing "Bringing in the Sheaves" while Jessica continues to complain about him not paying attention to her. After that, the whole congregation apologizes to Bart for indicting him. In the end, Jessica is punished and finds a new boyfriend, but she remains intrigued with Bart, who did not rat her out and, in turn, is still attracted to her. Jessica's punishment is washing the church steps and manages to trick Bart into doing it for her and then rides away on her new boyfriend's motorcycle. When Jessica is out of earshot he reveals that he plans to do a second rate job to get Jessica into even more trouble.