Spot Conlon and Jazzer Higgins are nineteen years old. Spot plans to propose to Jazzer, but when he asks Race for permission to ask her, Race gets angry and says no, then stalks off. When he doesn't come back later that night or the next day, the newsies set off the find him. Boots finds him in prison. Jazzer's feelings are all over the place: She feels like Spot is avoiding her, Race doesn't approve of her and Spot's relationship, and new Race is in jail. Spot tries everything in his power to get Races consent, get Race out of jail, and plan the perfect romantic setting to propose. Will things end up happily ever after like they all hoped?