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Recently I came upon this question in an English test:

All the people hated Sally. However, ____ learning that Terry was the defense lawyer in this court case, they were on Sally's side.

The given answer is "upon", but I think that "despite" should also be an acceptable answer, just that it changes the meaning of the sentence. (No additional context was provided to indicate the intended meaning.) Are "upon" and "despite" equally correct answers, considering both grammar and logic?

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    The context is there. They hated Sally but now they support her. Upon suggests a point in time when something changed.
    – Stuart F
    Jul 3 at 9:59
  • What if the sentence was simply stating that even with a key factor (Terry being the lawyer) that should've gotten the people to change their minds, the people still sided with Sally, the person they normally wouldn't support? Would "despite" be acceptable in this situation? Jul 3 at 10:16
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    Would the downvoters and close voter please explain themselves. This is a very tricky usage issue, and I haven't found an answer in any of the normal usage sites except for one buried deep in the comment section below the actual article.
    – Phil Sweet
    Jul 3 at 13:53
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    Using 'despite' is grammatical and makes a certain sense, but the situation where 'upon' fits is a far more likely scenario. Ultimately, 'correct' answers in tests often depend on the propensities of setters. Jul 3 at 14:12

2 Answers 2

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Neither upon nor despite is great here, but upon is less bad. After would be better because it agrees with the resultative aspect of were on her side. Upon is usually used for eventative focus, and that is unnecessary in the OP's example. "However, upon learning that Terry was the defense lawyer in this court case, they immediately changed to be on Sally's side."

Despite is a nonstarter here. Despite is used to introduce a condition that works against, but fails to change, the actual outcome.

I love to surf. I went today despite the iffy conditions.

I love to surf, but I had to work. I didn't go today despite the fine conditions.

In the OP's example, the introduced condition, Terry, did change the outcome, so despite can't be used there.

However, if you make it clear that everybody hated Sally but that they were already on her side, then it could work.

All the people hated Sally; but they were on her side despite learning that Terry was the defense lawyer in this court case.

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  • Did you mean to write "Neither upon nor despite is great here" or "Both upon and despite are poor choices here"? Neither one of those two versions is poor and so neither one is poor and either one is great, which means both are great. :)
    – tchrist
    Jul 3 at 17:42
  • @tchrist That sentence smells of the lamp. I changed it a couple times, and the proper verb wandered off.
    – Phil Sweet
    Jul 4 at 15:09
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These tests will often say to "select the best answer" for this reason.

You can twist a lot of contexts into different word selections. Taking your example you'd have to twist pretty hard.

A is true. Despite B, A is now false.

At best, there's missing context and the first statement is then misleading.

The word after may be more common that upon here.

All the people hated Sally. After learning that Terry was the defense lawyer in this court case, they were on Sally's side.

If we concoct a situation, we could actually reverse the meaning and use before.

All the people hated Sally. Before learning that Terry was the defense lawyer in this court case, they were on Sally's side. Everyone had loved Sally, but by picking such an unethical outcast as Terry, Sally herself had become a pariah.

If both after and before can work, you can likely make a lot of other words work as well. Lacking context, upon makes the most sense.

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