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There's another post concerning a similar question, but after reading through it, I'm still not sure about the meaning of the sentence I encountered:

The calendar was blank, as it had been every day this month, except for the third Thursday, where she had scribbled, Civic Association Meeting. Molly sighed, remembering a time when every day had held a different list of assignments and chores, schedules for Erik, and important meetings for Cole. Eight years ago she had needed a calm, almost boring, lifestyle to save her sanity. Now, she wondered if she hadn’t let it go on that way for too long.

Was Molly regretting that she had let herself live "that way" for too long, or was she missing being "that way" when she found she had nothing to do?

  • Since the if/whether clause refers to a binary choice, a negative clause has the same effect as a positive one -- after all, there are only two choices. So Molly was regretting continuing her calm, almost boring lifestyle now that her calendar was blank. – John Lawler Oct 19 '17 at 14:46
  • 2
    Not regretting, but questioning her own judgment about it. That interpretation seems to be confirmed by the grammar since the clause "if she had(n’t) let it go on that way for too long" is a subordinate interrogative (embedded question) where the meaning is "She wondered about the answer to the question 'Had(n't) she let it go on that way for too long?"' – BillJ Oct 19 '17 at 18:58
  • It seems to me the OP is overthinking the phrase. I don't see any difference in the behavioral consequences of the two posited possible interpretations. And, the whole paragraph would be highly contextual and related to the flow of action in the writing. The writer is attempting to give life and meaning to a character. The question should reflect how interpreting this phrase one way or another might change the character. – Corvus B Dec 5 '17 at 0:04
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Barid glossed over this, but I think this is the real only answer. Consider the difference between:
"Are you supposed to be at work?"
"Aren't you supposed to be at work?"

"Do you have a dollar?"
"Don't you have a dollar?"

"Well, is that special?"
"Well, isn't that special?" (See Church Lady)

"Has this gone on for too long?"
"Hasn't this gone on for too long?"

They are not exactly equivalent. That negative suggests the speaker thinks you are supposed to be at work, you do (or should) have a dollar, that is special, and this has gone on too long, and is offering you the chance (or daring you) to deny it. Putting "wondered if" in there makes it a little gentler, but she is not feeling neutral about the question. Her internal dialogue may well be, "Haven't I let it go on this way for too long?"

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It's a kind of self realisation when we question ourselves weighing the options available, scales down one in preference to other or even luxuriate in indecisiveness. You may call it repentance, or — even may not. BILLJ in his comment has nicely balanced grammar and literature. For argument's sake let us imagine the highlighted portion of your text a direct speech which the writer has rendered indirect. In a CLOSE ENDED question as this the subordinating conjunction is IF/ WHETHER meaning both the probabilities. However if such close ended questions are in negative, they suggest affirmation by negation.

  • Isn't that lady Boby Simpson?

So in our example Molly casts a longing lingering look behind and thinks — perhaps — those days were short lived. ---------------------------------

I thought it necessary to add our grammar class transformation exercise we practised in school days in support of what I have already said.

  • He is too weak to go. (He is so weak that he cannot go.)

  • He is too weak not to go. < May sound odd > (He is not weak enough that he cannot go.)

    She wondered if she had not let it go that way for too long. Let us simplify it.

  • It was too long not to let it go that way.

Are we not inclined to say it was not long enough that she should not let it go that way?

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She is thinking that it might not have gone on for too long. Take the second half, "let it go on that way for too long" and then add the negative, reversing the meaning "hadn't let it go on that way for too long".

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