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"He thought that that might be awkward."

I know this sentence is a bit awkward, but is it grammatically incorrect?

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It may sound awkward, but it is grammatically correct.

The answers to this question exhibit more awkward ones: Awkward sounding but grammatically correct sentences?

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+1 for the awesome link – David Smith Jan 13 '11 at 23:27

There's nothing wrong, IMO, with re-wording the sentence if you feel it sounds awkward. For example (with a context I provide):

"Jim thought reprimanding her would be appropriate. Bill, on the other hand, thought it might be awkward." (The indefinite pronoun "it" replaces "reprimanding her.")

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