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I found this sentence when looking up diffidence in dictionary:

I say this with some diffidence.

I think normally the action of saying is done in the past, so it's more natural to say :"I said this with some diffidence."

If it uses present-simple tense, then it is a statement or status, stating that every time I happen to say it, I will say it with diffidence, but it's strange that someone makes that statement.

Of course above things are just my little comprehension of English, so I could only write them with diffidence.

Anyway, how to comprehend this sentence? In what situation would someone write this sentence?

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    Probably as a temporary action, use the continuous form: I'm saying this with some diffidence. – Alejandro Feb 5 '16 at 14:07
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We can refer to ourselves in the act of speaking, usually for rhetorical emphasis of some kind. We are characterizing our attitude towards the words we are speaking. It could be concessive, or a disclaimer, for example, or some kind of "softening" politeness.

I say this with all due respect, but you must try harder to discourage your child from acting out in class.

I say this with great regret, but the committee has voted to reject your application.

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You understanding of using the present tense to show repetition is correct

I say "Good morning!" to my neighbour

However, this in your example shows specific single use

I say this with some diffidence

means you are currently saying something in a particular way

I say this with all my heart: I love you!

does not mean everything you say is so emotive

The speaker would use this either before or after saying something that they are being diffident about

I say this to be perfectly clear

means the speaker is telling you something she there is no misunderstanding.

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