When Homer’s attempt to fix the family’s hot water heater turns disastrous, he takes refuge at Moe’s tavern. There Moe grouses about his status as a single man. Homer takes pity on Moe and escorts him to the darkest bar in town. But prospect after prospect turn away. Just when Moe is about to give up, he draws the attention of an attractive woman, Renee, who sells flowers. Renee takes pity on the vulnerable bartender and accepts his offer for a date. The pair hit it off, and Moe begins spending a great deal of money courting his potential bride. As time passes, Moe discovers he has maxed out his credit card. A desperate Moe realizes his automobile is worth five thousand dollars, and convinces Homer to help him steal it.

Moe devises a scheme in which Homer is to steal the car while he is attending a charity cruise with members of the Springfield Police Department and then park the vehicle on railroad tracks. After the car is demolished by a train, Moe intends to collect on his insurance policy. The night of the cruise arrives. After the ship sets sail, Homer steals the car. But instead of driving directly to the railroad tracks, he stops at a drive-in movie theater. Homer falls asleep, only to be awakened by the sound of the train zooming past. Realizing he must find another way to destroy the car, Homer heads towards a cliff. Unfortunately, Homer becomes trapped inside, and plunges into the waters below as Wiggum watches from the ship. Police place Homer under arrest. Homer is convinced that Moe will clear his name and tell the police he didn’t steal his car. But Moe maintains that if he changes his story and admits the truth, he will end up behind bars. Instead of helping free his friend, Moe plans a vacation with Renee in Hawaii.

Moe tells Renee the truth about Homer stealing the car. But instead of going directly to the police, Moe tries involving Renee in a plot to fake their deaths by burning down the bar. A shocked Renee leaves Moe for good. Meanwhile, Homer escapes from jail to avenge his false imprisonment. He makes his way to the tavern, which Moe is in the process of burning. The pair are overcome by smoke, but Barney drags them to safety. Homer forgives his friend for his misdeed. He then offers Moe his own home as a temporary tavern.