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Original text:

How it was that he should have guessed what she meant at that very moment I cannot tell.

Can we cut down the sentence to the following?

How he guessed what she meant at that very moment I cannot tell.

I thought "should have done" alawys means pretty much what you said "you were supposed to do it", and it generally implies that "you did not do it".

In this case, does the "should have guessed" have a different meaning like "managed to guess what she meant", "did guess what she meant"?

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  • With 'How he guessed' there's more emphasis on 'his' spectacular guessing abilities. Compare 'How he reached the green from that lie I'll never know.' With the (more often associated with UK usage) original, the emphasis is more on the remarkable guess itself. Nov 8 at 19:06
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There are several things to pick apart here. First, about "should have": Yes, there is another meaning for should. (And the have is just along for the ride as part of the verb tense.) Looking at this Lexico entry for should, you're thinking mainly of definition 1, "to indicate obligation, duty, or correctness." But note definitions 3 and especially 4:

  1. formal (expressing the conditional mood) referring to a possible event or situation.
    ‘if you should change your mind, I'll be at the hotel’
  2. Used in a clause with “that” after a main clause describing feelings.
    ‘it is astonishing that we should find violence here’

That's what we're dealing with here. You could replace "should" with "could" or "might" without altering the meaning greatly.

To the phrase "how it was that," which you mention in the title, it's true that it's a bit redundant. First of all, if we straighten out the contorted syntax of the original, we get:

I cannot tell how it was that he should have guessed what she meant at that very moment.

Yes, you can arrive very nearly at the exact same meaning simply by leaving out it was that:

I cannot tell how he should have guessed what she meant at that very moment.

A hair-splitter might point out that there is a fine shade of distinction in meaning here. This altered sentence says that we can't tell how he should have guessed—by what mechanism he should have gone about guessing. The original says that we can't tell how it should come to pass that he could guess. "How it was" means that we're having trouble explaining a reality, rather than "how" that reality is executed.

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  • Thanks Andy, you definitely help clarify my questions.
    – bhes 203
    Nov 11 at 2:44
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(At that moment could modify the guessing or the meaning. Final adverbial phrases in complex sentences are almost always ambiguous. So let's ignore it, shall we?)

  • How he guessed what she meant I cannot tell.

comes via Topicalization from

  • I cannot tell [how he guessed [what she meant]].

That's three verbs, so three clauses. The main clause has a Wh-complement clause starting with how as its object. That object clause has another Wh-complement clause what she meant as its object.

Complement clauses come in several varieties, and can always be augmented:

  • I don't know how it happened that he guessed what she meant.
  • I don't know how it happened that he might have guessed what she meant.
  • I don't know how it happened that he might have guessed what she seemed to mean.

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