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Now that I think about it, it was from that moment where I started to have doubts about him.

Would it be better to use the word "when" instead of "where," or are they both equally valid word choices? Is there any difference at all?

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up vote 6 down vote accepted

It should be:

Now that I think about it, it was from that moment that I started to have doubts about him.

It sounds a bit awkward with all those thats, but "that" is grammatically correct. It might read better this way:

Now that I think about it, that was the moment when I started to have doubts about him.

Or better yet:

That was the moment when I started to doubt him.

I'm not sure if where or when would be incorrect grammatically speaking, but either would be confusingly redundant, as they serve essentially the same purpose as the prepositional phrase from that moment -- i.e., to specify a point in time. Thus, if I hear the sentence with either when or where in the place of that, it sets an expectation that it refers to yet another point in time at which something else happened after you started to have doubts, e.g.:

...it was from that moment when I started to have doubts about him that I began trying to hack into his e-mail account to see if he was cheating.

In short, if you use when or where, the thought feels unfinished to this American English speaker.

That, on the other hand, serves as a conjunction introducing the subordinate clause "I started to have doubts about him." Thus, it completes a thought.

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...In your second and third examples I would just leave out the "when" entirely. That's just my opinion. – kitukwfyer Apr 1 '11 at 1:55
Could I replace "Now that I think about it" with "If I think about it now?" Is using "when" or "where" grammatically incorrect? – language hacker Apr 1 '11 at 1:57
@language hacker: Yes, replacing "now that..." with "if I..." is fine. I edited my answer to address grammaticality. – Kelly Hess Apr 1 '11 at 3:02
@kitukwfyer: Good idea! – Kelly Hess Apr 1 '11 at 3:03
You used "when" together with "that was the moment." Would it also be grammatically correct to say "it was from that moment when?" – language hacker Apr 1 '11 at 3:23

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