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I came across this sentence :

"many a man has shot himself on finding himself in such a position"

. I am not getting what is apt meaning of the phrase 'many a man' if a singular term - 'himself' is used in this sentence.

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    How would you convey in your language the idea that a person had spent many happy days visiting a particular place, without suggesting that these happy days were all part of the same extended visit? They took place at a number of different times in this person's life. The focus is on the individual day even though there were many such days. I spent many a happy day there.
    – TimR
    Commented Nov 7, 2018 at 9:37

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"Many a man has shot himself on finding himself in such a position" means the same thing as "many men have shot themselves on finding themselves in such a position".

Both ways mean that many men have done this. The choice of using singular is just style, and how the author wants us to imagine it in our minds (perhaps they want us to see a single, unfortunate, lonely man instead of a whole group of men).

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    +1. Yes, the speaker does not want to create the image of a crowd of men all shooting themselves. The emphasis is on the individual.
    – TimR
    Commented Nov 7, 2018 at 9:33

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