When Professor Frink uses an astrology machine to ease the constant bickering between Bart and Lisa, they are given a sneak-peek into their final days of high school. In this future view, Marge and Homer are separated, Lisa is dating a muscular Milhouse and Bart is dating the girl of his dreams, Jenda, guest-voiced by Amy Poehler. Much to their disappointment, both the relationships quickly flounder. In hopes of winning Jenda back, Bart takes a job at a Kwik-E-Mart, where he becomes the local hero after saving Mr. Burns from a robber. His reward is a scholarship to Yale that was initially intended for Lisa. Bart's deeper look into the future causes him to have a change of heart, ultimately affecting his present-day sibling rivalry for the better.

Bart becomes addicted to junk food when a new vending machine is installed at Springfield Elementary. His steady diet of processed foods leads to a massive weight gain and health issues. When he's unable to stick to his prescribed low-fat diet, the Simpsons stage an intervention and ship Bart off to "Serenity Ranch - A Forced Starvation Facility," headed up by former food addict Tab Spangler. While Spangler tries to help Bart overcome his obsession, Homer and Marge turn their home into a hostel for German travelers in order to pay for the costly Serenity Ranch.