Buster Keaton asks the father of the woman he loves for her hand in marriage, but the father wants to see Keaton make something of himself first. "I'll leave for the city to make good. If I'm not a success, I'll come back and shoot myself," Buster declares, which is a perfectly acceptable arrangement as far as the father is concerned. So Keaton heads off for the big city and tries his hand at a number of different jobs. But his letters to his girl suggest more noble and enterprising careers than those he's actually attempting. Her imaginings provide the basis for the title, while his actual efforts provide the humor.