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Are these two sentences different in meaning?

  1. They got him wondering if he should not have given up.
  1. They got him wondering if he should have given up.

According to me, they got him wondering about the same thing, but how can it be that the presence or absence of not can be so irrelevant?

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For me, (Southern UK), a hypothetical question about an action that has already been completed should refer to what he should have done, rather than what he actually did. Thus, if he did give up, you would use the first sentence. If he did not give up, you would use the second sentence.

An actual (rather than hypothetical) question should refer to the action that you think is the correct one, expecting an answer of yes. Thus, a parent might ask

Have you done your homework?

In the Northern UK (I can personally vouch for Scotland and Yorkshire), an additional not is often added to questions without the same overtone of suggesting the answer that you want to hear:

Have you not done your homework?

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  • I beg to differ. I think in both cases he has not given up, but wonders if he should (not) have :). If you put the sentence in the present, you get the same result. "They get him wondering if he should (not) give up." Point is, he has not given up!
    – fev
    Commented Dec 8, 2020 at 8:45
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    @fev if you disagree, why don't you answer the question yourself and explain your opinion more fully?
    – JavaLatte
    Commented Dec 8, 2020 at 11:28

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