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Why do you think the ‘look of disarming frankness’ put Gortsby on his guard

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Dusk by Saki

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In "Dusk" by Saki, why do you think that the young man's look of disarming frankness puts Gortsby on his guard?

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WILLIAM DELANEY eNotes educator | CERTIFIED EDUCATOR

It is evident from the description of Gortsby's observations and reflections that he makes a habit of sitting on a bench in this general area around dusk, probably shortly after he gets off work in some office, and watches the passing crowd. This would inevitably mean that he would be approached by strangers with hard-luck stories. Gortsby considers himself sophisticated. No doubt he has given people money in the past and then had second thoughts...