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How to understand "pinch-me" in this following sentence? a Trump presidency was a pinch-me prospect that too many people discounted.

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Well, "pinch me" as in "pinch me, I must be dreaming". So I'd say it means they couldn't imagine Trump ever really getting elected president. I don't think it's a common phrase at all, though. The phrase just has some alliteration in it to sound interesting.

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