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A says something insensitive, and then B's look in his face hardened. And then, A says:

I'm sorry, probably not the best time to be telling you that.

Would there be any difference if I would replace to be telling with to tell you that in that sentence?

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There is a subtle difference, made clear when you re-insert the words implied but left out from the sentences.

In the case of "I'm sorry, probably not the best time to be telling you that.", the full sentence would read "I'm sorry, this is probably not the best time to be telling you that."

In the case of "I'm sorry, probably not the best time to tell you that.", the full sentence would read "I'm sorry, that was probably not the best time to tell you that."

In the first case, the situation is in the present: the implication of using that wording is that the situation between A and B is still ongoing and uncomfortable.

In the second case the situation is technically in the past: the bad time to have told that truth was when it was told; of course the situation may still be ongoing and awkward, but there is also now a possibility that while it was a bad time to tell that truth, now that it is told it may be 'water under the bridge' and A and B may be moving on from it.

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