When Moe goes broke romancing a new love, he enlists the aid of Homer in an illegal scheme to collect $5,000 from his car's insurance policy. But after Homer botches the scam, Moe must find a way to bust his best customer out of the pen.
Homer witnesses Bart and Lisa having a "snowball fight" with ice cream scoops and points out that Marge told them they needed to take a bath. Although Bart points out she says "a lot of things", Lisa then points out that they can't actually take a bath anyway thanks to the water heater being broken, with Homer vowing to fix it. Unfortunately, Homer's attempt at fixing it by beating it with tools just results in the water heater exploding and causing half the house to be turned into a massive waterfall by the time Marge returns home, causing Homer to hurriedly run off to Moe's Tavern in an obvious attempt to hide from Marge's impending fury.
While at Moe's Tavern, Homer notices Moe's depressed state. After learning Moe has not had a date for four years, Homer plans to take Moe out to a night club to meet women. The trip proves to unsuccessful until Moe goes to leave, when a woman named Renee (Helen Hunt) talks to him. She treats him with basic human respect, better than he has experienced in a while, so he asks her out, and she says "yes".
Moe and Renee fall in love, though Moe feels forced to spend an excessive amount of money to impress her. When he maxes out his credit card, he decides to commit insurance fraud. He enlists Homer to steal his car and abandon it on train tracks so a train will destroy it. The night of the event, Moe and Renee go out on the "Police Department's Moonlight Charity Cruise", which ensures Homer that he will be safe from any police. However, Homer chooses at the last minute to watch a movie at a drive-in theater and fails to leave the car at the tracks on time. Bent on still trying to destroy the car somehow, Homer gets the idea of driving it off a cliff into a body of water. Unable to get out of the car in time, both Homer and the car plummet into the water near the charity cruise, directly in view of the police and Homer gets arrested for Grand Theft Auto.
Sent to jail, Homer is then assured that Moe will bail him out, but Renee talks about vacationing in Hawaii, causing Moe to have second thoughts. While packing his suitcases, Moe is confronted by his own conscience (in the guise of Homer), who makes him feel sorry for betraying his friend. Moe confesses everything to Renee, who at first respects Moe for telling the truth. But Moe proceeds to devise a scheme to get Homer out of jail illegally, which disgusts her, and she goes to leave Moe.
Moe's plan involves burning his bar down, but he drops a lit match before he intends to, quickly engulfing the bar in flames. Meanwhile, Homer has escaped jail on his own, planning his revenge on Moe. As he arrives at the bar, the two start to fight, but soon lose consciousness due to smoke inhalation. Fortunately, Barney emerges from the bar's restroom, rescuing the pair (as well as two kegs of beer). The tavern is completely destroyed, and Homer promises Moe he can use his house as a bar until he can rebuild the real thing.