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The title of the best seller book from Dale Carnegie uses the word "win" in an odd way to me. The most common usage would be "How to Make Friends and Influence People", wouldn't it?

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    Carnegie's target audience is people who aspire to be winners (in the game of life), so in context win is an appropriate verb. Apr 20, 2017 at 11:59
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    Consider the word winsome, which may have some bearing on this particular use of win.
    – Lawrence
    Apr 20, 2017 at 12:57
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    Literally the first meaning of win in MW is win. 1a. to get possession of by effort or fortune. b. to obtain by work.
    – choster
    Apr 20, 2017 at 17:49

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He's just using a different meaning win, where it refers to acquiring or gaining something as a result of a contest, like winning a prize. You might win a race in order to win a prize, but the prize is the only thing you take home with you.

In the context of Carnegie's book, making friends is treated as a challenge you take on for personal gain. The usage here is more like that in winning favour, or winning affection. Through the techniques the book teaches you, you will win people over as your friends.

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    Exactly. This is a metaphor, and the metaphor theme appears to be something like Friendship is a Prize in a Contest. The details of the contest, or game, being played, and of its participants, are open to contextual intrepretation (or, usually, ignored in an idiom like win friendship). Apr 20, 2017 at 13:20

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