"New Kid on the Block" is the eighth episode of Season 4.
Bart falls in love 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.
The Simpsons' next door neighbors, The Winfields, choose to move away to Florida for the prospect of warmer climes, and additionally, Homer's constant embarrassing behavior. To help them sell their house, the couple request Homer not to discourage potential buyers, with Homer bluntly refusing to do anything from covering his trash to taking in his old Jack-O-Lanterns, as well as disgusting buyers by sitting in a kiddie pool in his front yard.
Sometime later, Bart and Lisa explore the newly sold house out of curiosity, and go into the basement. Bart scares Lisa away through making up how the Winfields had a deformed son they forgot to take with them, but a beautiful girl takes advantage of his spooking, and surprises him, shocking himself unconscious. When he wakes up, the girl who checks up on him greets him, and that 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. In the meantime, Homer and Marge visit Ruth Powers at the house where she and Laura moved in--after Marge gives Ruth a "Welcome to the Neighborhood" basket, which includes a gift for "the man of the house," which appears to be Ruth, since it appears to be just her and her daughter. After noting that Marge seemed uncomfortable, Ruth (rather casually) explains that she and Laura's father got divorced a couple years previously, with her being the one to get custody of their daughter. Meanwhile, as Bart and Laura hang out, Laura later taunts Dolph and Kearney, two of the Springfield bullies, when they crudely try pickup lines on her. 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!", before leaving to attend to her new home. Bart says he is never going to wash that hand again, an act that is later undone when its filth becomes unmanageably adhesive.
Later, Homer can't find a babysitter for his and Marge's date, 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 seafood. Homer orders the all-you-can-eat and literally eats everything (according to one of the staff members, Homer proceeded to eat "all the shrimp and then took two plastic lobsters"), 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). In her testimony, Marge is reduced to tears as she recalls how she and Homer drove around for hours afterward looking for another all-you-can-eat fish seafood restaurant before he then went fishing. Winning the case, Homer instead negotiates with the captain and makes an out of court agreement, with Homer now allowed to truly have all he can eat, in exchange for being put on display in the restaurant for publicity as "Bottomless Pete, nature's cruelest mistake". Marge, of course, is humiliated.
Hoping to gain advice about relationships, Grampa gets a birthday visit from Bart, who then tells him about his failed relationship with the oldest woman in the world. Later, Bart talks to Homer about the subject, and which Homer is encouraged to teach his son about the facts of life, but fails upon coming to a drunken stupor. At night, Bart is called to a meeting by Laura in the treehouse, which Laura tells Bart the news that she is dating Jimbo Jones, who Bart feels both resentment towards him being the scourge of Springfield, and is no good for a girl like Laura.
While Laura and Jimbo kiss and make out during Homer's court case, 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 and cower in the face of danger, resulting in Laura realizing that he's no good for her, dumping him and kicking him out of the house. Laura tells Bart that she would date him if he were old enough to grow a mustache. Eventually, Bart and Laura make another prank phone call to Moe's and then laugh.