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 (guest star Anne Hathaway). 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.