Bart falls hard for his new next-door neighbor, young teenager Laura Powers. But try as he might, Bart can't get Laura to take interest in him romantically and is heartbroken when he finds out that Laura is in love with Jimbo Jones.
When the other neighbors, The Winfields, decide to move away because of Homer's constant embarrassing behavior. To help them sell their house they request Homer not do anything to discourage potential buyers, with Homer bluntly refusing to do anything from cover his trash to taking in his old Jack-O-Lanterns, as well as disgusting buyers by sitting in a kid pool in his front yard.
Bart and Lisa explore the abandoned house and go into the basement. Bart scares Lisa away, but a beautiful girl surprises him, and he knocks himself unconscious. When he wakes up, the girl says her name is Laura Powers, his new neighbor. Meanwhile, Homer watches an advertisement on television about the "Frying Dutchman," an all-you-can-eat seafood restaurant run by Captain Horatio McCallister and wants to go.
Bart develops a crush on Laura. Meanwhile, Homer and Marge visit Ruth Powers at the house where she and Laura moved in. Ruth tells them she is divorced. Meanwhile, Laura taunts Dolph and Kearney, two of the bullies. Laura looks at Bart's palm and predicts that he is going to be rich. She spits in his hand and says, "And there's the swimming pool." Bart says he is never going to wash that hand again.
Homer can't find a babysitter, so Bart suggests that Laura should babysit them, to which Homer agrees. Bart then takes a bath and dresses up to impress Laura. When she arrives, they share dinner and Bart even accepts a dance with her.
Meanwhile, Homer goes to the restaurant with Marge, ignoring the fact that Marge is allergic to fish. Homer orders the all-you-can-eat and literally eats everything, continuing to eat well past closing time and completely taking unfair advantage of the offer. Captain McAllister finally kicks a struggling Homer out after midnight, since even after hours of constant eating he still wasn't full. He goes to trial with his lawyer, Lionel Hutz, claiming false advertising (with help from an entire jury of obese people). Homer and the captain make agreements. Marge is humiliated that he became the entertainment there as a "remorseless eating machine" or "nature's cruelest mistake". After a meeting in the treehouse, Laura tells Bart she's dating Jimbo Jones.
While Laura and Jimbo kiss, Bart makes a prank call to Moe's Tavern, posing as Jimbo. Moe then comes over and threatens Jimbo with a rusty kitchen knife, causing him to burst into tears, resulting in Laura dumping him. His fate remains unknown afterwards. Eventually, Bart and Laura make another prank phone call to Moe's and end up laughing.