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Which case is correct? I'm writing like some kind of fanfiction, but I really want to know and get better in grammar.

"He had been unable to sleep well the night before to the morning where he had to go away."

"He had been unable to sleep well the night before to the morning in which he had to go away."

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    Morning takes the preposition on in this case: "the morning on which he had to go away." – Kris Jan 25 at 8:25
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Of the two options you've given, "in which" is more correct. I believe “in” is technically correct since it would be grammatically correct to say “in the morning”. However, morning is a time, so "when" could work better than your options:

"He had been unable to sleep well [from] the night before to the morning when he had to go away."

or don’t use a preposition:

"He had been unable to sleep well [from] the night before to the morning he had to go away."

Adding “from” as indicated above would make the sentence grammatically correct, but your sentence could be much more concise. It seems like this is referring to a time in the past, and the morning already passed in the narrators frame of reference. In that case, you might consider:

"He couldn't sleep the night before he left."

Or if your character didn't end up leaving, and you don't yet want to disclose that, you could say:

"He couldn't sleep the night before he was to depart."

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    The first sentence you've offered as a solution is incorrect - it's ungrammatical to say "before to", and no native speaker (excluding unusual regional dialects) would ever use this construction. – Reinstate Monica Jan 25 at 5:45
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    I don’t think we’re reading this sentence the same way. I read “to” as meaning the same as “until” in this case, so I believe it would be technically correct if “from” was added between “well” and “the night”. My first sentence answered the OP’s specific question. But since it’s obvious that no native speaker would use the construction in the OP, I didn’t suggest “from” to fix, but instead suggested two re-writes, – mRotten Jan 26 at 8:28
  • I’ve now updated my answer to reflect my understanding of the OP’s sentence. – mRotten Jan 26 at 8:54
  • The edit addresses the grammar, but not the logic: no one would say they couldn’t sleep from the night before till the next morning, since the second phrase is obviously redundant. It’s an error in the OP’s sentence. – Reinstate Monica Jan 26 at 11:31
  • @Chappo, I disagree. If you can’t tell me what rule the sentence breaks, you can’t say the sentence is objectively incorrect. The phrasing is admittedly very awkward, but I preserved the phrasing that I believe the OP intended, which is technically correct if you use “from”, and my re-writes address the awkward phrasing. The reason I did not address this in my original answer was to avoid this very discussion. I understand your argument, but I am nonetheless satisfied with my answer. – mRotten Jan 26 at 17:49
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Neither of your sentences is actually correct.

First, you should you not use before to in your constructions—drop the to and just use before on its own.

Second, both where and in which are inappropriate. Instead, you should use when or on which. Alternatively, you don't need to use anything at all.

As such, the following would be fine:

He had been unable to sleep well the night before the morning when he had to go away.
He had been unable to sleep well the night before the morning on which he had to go away.
He had been unable to sleep well the night before the morning he had to go away.


Since you're talking about the night before, it's also assumed that what comes after that is the next morning or day.

So, if you want to simplify it even further, you could use:

He had been unable to sleep well the night before he had to go away.

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