Homer tries to help Moe meet a woman. After having no luck at Stu’s Disco, Moe finally meets a woman named Renee selling flowers. They strike up a conversation, and Moe asks her out. She accepts.

Romance blossoms between Moe and Renee. Moe begins to spend a great deal of money on her, and soon his Players Club card is maxed out. Desperate to get more money, Moe decides to commit insurance fraud by asking Homer to steal his car and park it in front of the 10:15 train while he and Renee are on the Police Midnight Charity Cruise.

Homer steals the car but fails to stick to the plan. Missing the train because he goes to a drive-in movie, Homer decides to dump the car into the ocean, but winds up getting caught in the act by the police on the charity cruise. Moe lets Homer take the rap.

Moe takes the money from the insurance company, but instead of bailing Homer out of jail, he plans a trip to Hawaii with Renee. Before they can leave, Moe is seized with guilt and confesses the whole thing to Renee. Renee is initially forgiving, but when Moe tries to put together another scheme to avoid telling the truth, she leaves. Moe accidentally sets the bar on fire, just as an escaped Homer arrives to exact his revenge on Moe. Homer and Moe succumb to smoke inhalation and are saved by Barney after he first saves some kegs of beer. When the duo come to, they wake up and apologize to each other. To help him get back on his feet again, Homer allows Moe to convert the Simpson home into the new site of Moe’s Tavern.