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1 I am surprised that he should say that yesterday.

2 I am surprised that he should have said that yesterday.

I think that they mean almost the same but they are not identical. What's the difference?

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    I don't think there is any difference in meaning.
    – Kate Bunting
    Commented Sep 23, 2023 at 11:06
  • We're much more likely to be ...surprised that he would say that today. But note that yesterday in your example can't affect the syntax, because the speaker can only be surprised if he really did say it (in the past). If him saying that wasn't a definite known thing that really happened in the past, it would be expressed as I would be surprised if he said that (yesterday OR tomorrow).
    – FumbleFingers
    Commented Sep 23, 2023 at 14:09

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should is a reported speech marker there, "is alleged to have said". (Compare German sollen in newspapers and TV news when the news person is speaking of something alleged to have been done or said by somebody.) The speaker is not conceding that he actually said such a thing.

I am surprised that he should say such a thing.

Paraphrase: I think he would never say such a thing. I am surprised to hear (from someone) that he did. Or I am having trouble "believing my own ears".

I am surprised that he should have said such a thing.

Paraphrase: I think would not have said such a thing. I am surprised to hear that he did, or ditto (... own ears).

*I am surprised that he should say such a thing yesterday.

I'm marking that one as unidiomatic because of yesterday. Paraphrase (unidiomatic): I think he would never say such a thing yesterday.

I am surprised that he should have said such a thing yesterday.

Paraphrase: I think he would not have said such a thing yesterday and I am surprised to hear that he did, or ditto (... own ears).

I am surprised that he should have said such a thing yesterday, of all days.

I think he would not have said such a thing yesterday, of all days, and I am suprised to hear that he did, or ditto (... own ears).

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He should say is present (or future) tense:

I’ll be ready with the hose in case a fire should break out

He should have said is past tense:

With his grandmother now dead, he would never learn why she should have done it that way.

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    You have completely mangled and distorted my examples up to the point that your answer answers a question which I didn't ask. My first sentence legitimately refers to the past while your first sentence makes a reference towards a future action. They are incomparable. Plus you completely disregarded the presence of "I am surprised" which brings the subjunctive at play.
    – user1425
    Commented Sep 23, 2023 at 10:46
  • Well that’s quite a warm reception. What do you reply to those who intended to ruin your day?
    – Paul Tanenbaum
    Commented Sep 23, 2023 at 18:18

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