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In a website, there is sentences like the below.

▶Whenshould have Clark started wearing glasses?

I am not sure when he should have begun wearing the glasses but it should not have taken this long. He has been seen so many times without the glasses.

In a dictionary 'should have p.p.' usually have meaning to regret about a past activity. (e.g.▪ You should have been more careful.)

Could you tell me the exact meaning of "should have p.p." in the questioned sentence, and give me another example sentence for this meaning?

["Should have p.p." seems to me to have almost the same meaning with "might have p.p." or "could have p.p." or just "have p.p." I'm not sure. It's just so confusing!]
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Stenka25In a website, there is sentences like the below.
▶Whenshould have Clark started wearing glasses?
I am not sure when he should have begun wearing the glasses but it should not have taken this long. He has been seen so many times without the glasses.
Can you please give the link for the website? It doesn't seem to be giving good information.

CJ
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OK. I checked the link. The question itself is not right. It should be:

When should Clark have started wearing glasses?

This solicits opinions about when (during a series of television programs) it would have been advisable for the writers to direct Clark to wear glasses. The advisability meaning of should is the most common, so there is nothing strange about this use of should. It's just the discussion itself that is a bit unusual. Emotion: smile

CJ
CalifJimWhen should Clark have started wearing glasses?

Can't the "should" mean "must", meaning, "When do you think Clark started wearing glasses?"?
Isn't this interpretation allowed or is this very unusual?

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pructusCan't the "should" mean "must", meaning, "When do you think Clark started wearing glasses?"?

No. It doesn't ask "When do you think Clark started wearing glasses?"

It asks "In your opinion, at what point in the TV series would it have been advisable for Clark to start wearing glasses?"

Believing that something happened is not at all the same as believing that it would have been a good idea if that thing happened.

CJ

I see....

Thanks so much, CJ!!

Still, something is vague in my mind.

For example, They should have arrived there by now. will be interpreted to mean probability.

Then, When should Clark have started wearing glasses?, can't it mean probability?
Like, "When should they have arrived home?"?

I mean, without any context or in different context.

There are two meanings of 'should' — the 'should' of advisability and the 'should' of expectation. (In your post you called expectation 'probability'. It's the same usage.) If the context is unclear or unknown, the exact meaning of 'should' will also be unclear in some cases.

They should have arrived there by now. This involves expectation more than advisability. The speaker expects (speculates) that they have arrived there by now, not that it was advisable for them to arrive there by now.

When should they have arrived home? This could be advisability or expectation. When was it advisable (a good idea) for them to arrive home? / When were they expected to arrive home? Without further context, we can't say which kind of 'should' is really intended.

When should Clark have started wearing glasses?
This sentence has the same form as the previous example, so this could also be advisability or expectation. When was it advisable for Clark to start wearing glasses? / When was Clark expected to start wearing glasses?

In the given context, however, my personal feeling is that advisability is more prominent than expectation, though I admit that both are involved in a sort of blend. The context shows us that it is more about what was advisable for the director of the series to do (tell the actor to wear glasses) than what it was advisable for Clark himself to do (put on glasses). This is because Clark is a fictitious character created by the writers.

But, to a lesser extent I think, it could also suggest that the audience who follow the series would have expected the character Clark to start to wear glasses at a certain time within the series. For me, it's easier to take the viewpoint of the director and what it is advisable for him to do than to take the viewpoint of the audience and what they expect to happen in the series.

CJ

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Wow....

This is so insightful and helpful, CJ!!
I hope this kind of clear explanations can be written in a book, maybe ebook, at the least.

Thank you so so much!!