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I have problems with this sentence. First of all:

What does "Who should I say is calling" mean?

Does that mean:

To whom should I say is calling? Or it means: Should I say who is calling?

And also I have problems with the grammar structure, in the second clause:

Who should I say is calling? , Shouldn't the second clause have a subject, like " [...] It *is calling**?

Also: Is this stuffy English? Does this sound right to you? Or old-fashioned?

Thanks a million.

2

Let's rearrange the clauses in the sentence into a simpler form, and then build back up to the more complicated form you're asking about.

Alice is calling - simple statement of an action in progress

I will say (that) Alice is calling - an additional clause to describe what I will do in response to the initial action. When I tell someone about the phone call, I am going to say that it's Alice that is calling.

Should I say (that) Alice is calling? - rephrased as a question, so the verb (should is moved to the beginning). This sentence is ambiguous on its own, but in this context, it might mean: I know that Alice is calling, but should I tell someone that she is calling? Alternatively, it could mean: I am going to tell someone that a person is calling; should I tell them it's Alice (or someone else)?

Who should I say is calling? - "Alice" is replaced by the pronoun "who," which is moved to the beginning of the sentence. The meaning is: I am going to say (to tell someone) that someone is calling; who (what name) should I say it is?

It's very typical English. Not stuffy or old-fashioned, but polite. A less polite version might be "who is this?" or "can I have your name?"

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Who should I say is calling

is asking the name of the person is calling.

If you are asking for the name of the person that the person calling wants to talk to, you say

To whom do you want to speak?

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Suppose someone calls on the phone and asks to speak to, for example, Bob. You could yell, "Hey, Bob, someone on the phone for you!" But it's considered polite to give him a little more information. You'd like to be able to say, "Sally is on the phone for you." So you want to ask the caller to identify themselves. Thus you ask, "Who should I say is calling?"

"To whom should I say is calling?" would be incorrect grammar. The person calling is the subject, so it should be the subjective case, "who". And you're asking who is calling, not who they want to speak to. If you wanted to ask who they want to speak to, you would say "Whom do you want to speak to?" (Or if you go for that "never end a sentence with a preposition" rule, "To whom do you want to speak?")

If you ask, "Should I say who is calling?", technically that is a yes or no question. It invites the other person to say "no". In real life asking a yes/no question like this is often considered a polite way of asking the real question, namely, "who is this?"

And by the way, you could simply ask, "Who is this?" But that sounds demanding and rude. It seems more polite to ask, "Who should I say is calling?" Or the other common phrase is, "Who is this speaking, please?"

And by the way, a side note on etiquette: If the person they want to speak to isn't available, it sounds better to tell them this BEFORE you ask who is calling. If you say, "Who should I say is calling? Oh, Sally Jones. Well, Bob isn't here right now", then it sounds like if it was someone else calling that maybe Bob would be there right now.

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on the phone, you could use the expression "should I say who's calling" to ask the speaker if they'd like you to announce their name to others (who might be present there.)

imagine this scenario

someone calls you, and leaves a message for your brother but they they feel like your brother knowing who left the message is irrelevant and unimportant, so in response to the question, "should i say who's calling", they'd say, "no, it's not necessary"

another example:

the phone rings, you answer it. you don't recognize the caller. they say they want to talk to your dad. at this moment you might ask something like, "who should i say is calling" to get the speaker's name.

So the said expression doesn't mean, "to whom should I say is calling" rather it means, "should i say the name of the person who's calling"

and about the grammar: it's a case of questions within questions:

who's calling? should I say it?

the first question is embedded in the second

should I say who's calling? (we call these embedded questions)

and no you don't need a subject since who is the subject of is calling

more examples of embedded questions

who's there? tell me

tell me who's there

who ate the pizza? should I say it?

should I say who ate the pizza?

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