While at Moe's Tavern, Homer notices that Moe is depressed because he cannot get a date. Homer decides to take Moe out to meet a woman. The trip to a disco proves to be unsuccessful, but on their way home, a flower vendor named Renee starts a conversation with Moe, and he ends up asking her out.
Moe and Renee seem to form a strong relationship, but Moe is insecure about his hold on her and he feels he must spend large amounts of money on food and entertainment so she will stay with himi. Upon maxing out his credit card, Moe comes up with a scheme to commit insurance fraud by having Homer steal his car and park it on train tracks so it would be destroyed, paying off for thousands of dollars and allowing him to "keep showing Renee the sweet life". The night the scheme is supposed to take place, Moe and Renee attend a police charity event aboard a yacht; the event's attendance by all the officers in town ensures Homer will not get caught perpetrating the scheme, and gives Moe an alibi so that no one will suspect he was behind the act. Homer botches the plan by stopping to watch a drive-in movie, while the train they were counting on to destroy Moe's car passes by. Deciding all is not lost, Homer drives the car over a cliff — but his attempt to exit the car before it sinks into the water below fails. The car ends up sinking just near the yacht where the police charity event is taking place, and when Homer swims to the surface, he is arrested.
Moe speaks to Homer through the bars of his jail cell window and promises to bail him out, but changes his mind when Renee talks about wanting to vacation in Hawaii. He uses the insurance money to book the trip instead of bailing Homer out of jail. While packing, Moe is confronted by his own conscience, in the form of Homer, who makes him feel bad for his betrayal. Moe ends up telling Renee the truth about the insurance fraud scheme, and she is at first happy he was honest. However, when Moe starts scheming again for a way to get Homer out of jail without paying the bail, Renee is disgusted and leaves him.
Moe's idea involved setting his bar on fire, which he ends up doing by accident before he realizes Renee has left. Meanwhile, Homer escapes jail by attacking Hans Moleman, who was delivering books to the inmates. He enters the burning bar to confront Moe, and the two start fighting. They are both soon rendered unconscious from smoke inhalation, but Barney, who has been in the toilet for the duration of the scene, appears and rescues them (after first saving two kegs of beer). The bar is completely destroyed, and during their reconciliation Homer promises to help Moe get back on his feet. In the final scene, we see that Homer has allowed Moe to relocate his bar to the Simpsons' home.