When Bart is forced to chaperone Jimbo's girlfriend, Shauna, to a movie, Shauna develops feelings for Bart, resulting in serious trouble with the bullies at school. Meanwhile, Homer buys a new treadmill, which comes with an online TV website, and becomes hooked to the show "Stranded".
During a day in the mall, Homer chooses to dump off Milhouse and Bart at a children's movie to eat at the food court. Bart is forced to chaperone Jimbo's lover Shauna to a Jennifer Aniston movie. The pair leave shortly after watching the only scene of the movie that appeals to Shauna (the man's butt) and they hang out in the mall. Bart and Shauna meet again per Jimbo's demands at a boutique were Shauna shoplifts a bottle of perfume and puts it in her bag but sets off the alarms when she tries to leave and is caught by the security guard, but Bart bails her out out of fear of being beaten up by Jimbo. She shows her appreciation by lifting up her tube top and flashing her breasts for him as a reward, leaving him positively traumatized, obsessed with her breasts and smitten with her. They plan to enter a romantic relationship of kissing and showing Shauna's chest to Bart to spite Jimbo and it is not long before Bart becomes the target of Jimbo's wrath. The pair attempt to take shelter at Comic Book Guy's store, while Jimbo plans to stake out Bart's home with help from an oblivious Marge, so Bart ultimately has to return home and face Jimbo's wrath. Shauna breaks up with them ultimately and with some prompting from Lisa, Bart receives his due punishment (being held upside down from his treehouse to have the "fear of God put into him") from Jimbo.
Meanwhile, Homer is persuaded to buy a state-of-the-art treadmill from a crafty salesman. When Lisa shows Homer that he can access television shows wireless, he takes advantage of the machine and develops an obsession with watching an old television show called Stranded, instead of working out. Eventually Marge, in a fit of discomfort, gives away all the spoilers of the episodes Homer has not watched yet. He is initially outraged at Marge and threatens to divorce her for ruining the episode, but a romantic evening planned by her resolves matters.