When Homer and Marge's marriage turns out to be invalid because Reverend Lovejoy was not licensed at the time, Homer asks Marge to marry him again. But when Homer mysteriously disappears on their wedding day, Bart and Lisa search for answers and are led on a cryptic trail of clues, leading them to Sideshow Bob. Meanwhile, Homer finds himself chained to a pipe in a dark room. When a mysterious voice tells him that the key to unlock his chains is inside a lollipop, he frantically eats it only to discover the lollipop is made of fiery hot sauce and he is tormented as Bart and Lisa race to save him. Blackboard: 'My piggy bank is not entitled to tarp funds'.

When Bart and Milhouse pull off a prank at Springfield Elementary, Milhouse takes the fall and gets suspended from school. Homer forces Bart to sign in under Homer's name and visit Grampa at his retirement home, and Bart soon becomes smitten with a delightful 11-year-old volunteer named Jenny. Hoping to impress Jenny, Bart offers to volunteer at the home. But as Bart and Jenny's relationship progresses, Milhouse emerges from his suspension and is less than thrilled about Bart turning his back on him for a girl. Meanwhile, Lisa does a report on what Springfield will look like in 50 years and becomes very depressed at the dreary outlook. A concerned Marge takes Lisa to a psychiatrist who diagnoses Lisa with Environment-Related Despair and puts on her on an antidepressant to cure her eco-blues. Blackboard: 'I will not mock teacher's outdated cell phone'.