Initially, the old gentleman with the umbrella makes a particularly positive impression on our narrator in Roald Dahl’s short story. She describes the old man in flattering terms, referring to the fact that he is “well-dressed” and “polite.” She is embarrassed at the suspicious way in which her mother is treating the man. Based on the man’s shoes, our narrator believes him to be a gentleman because her mother has taught her that “you can always spot a gentleman by the shoes he wears.” In the narrator’s eyes, the man comes across as a kind, but somewhat helpless elderly man who is worthy of respect and assistance.

It is clear from the non-verbal conversation that our narrator has with her mother through her own "frosty-nosed [look]” that she believes that this gentleman is not someone who should be taken advantage of.

However, after the man has received his pound and gone on his way, it is the narrator and not her mother than gets the first inkling that they have been duped. She watches the man crossing the road and comments that despite how old and tired he had made himself out to be, he doesn’t appear to be tired at all. By the time they have watched him through the window of the pub and worked out exactly what his game is, our narrator has disbelieving respect for the conman, labelling his con as “neat” and “super.”