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How natural or unnatural is the following sentence, which was suggested by a native speaker (it might not be the exact wording, but 'paid' was surely used)? It would be helpful to me if you would show me the formal version and the casual version.

Tell me how much you paid when you come back from the dentist.

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As a 50 year old native U.S. speaker who cares about using "proper English" (without being a professional writer or grammar professor), this sentence does not faze me in the least. In other words, I think it is perfectly fine.

I don't see a definitive answer to your question, as currently phrased, so I'll just take a stab at some other versions. There are things to be gleaned here.

"Please tell me how much you paid when you come back from the dentist." -- just sounds more polite, less like a command like the original, but nothing to do with "formal/informal."

"When you come back from the dentist, please tell me how much you paid." -- just switching the clauses works when also separated by a comma there. My reason for switching would be to prepare the listener for "when" I'm asking them to do something (i.e., not now), before they hear "what" I'm asking for. Unless I wanted them to hear the "what" first, then the "when."

Off-the-cuff, I honestly don't see a way to make this one more formal, and the only way I see to make it more "casual" is to replace with slang or otherwise make it sound less educated, like:

"Hey! When you get back from that tooth doctor, let me know what the damage was." :D

Here, let me just offer a few phrase replacement options to consider:

  • tell me => let me know -- makes it more casual
  • tell me => inform me -- makes it sound more formal, but overly "stuffy"
  • come back / get back => return -- makes it sound slightly more educated
  • paid => what the damage was -- not "the damage" to one's teeth; this is American slang ... "What's the damage?" is somewhat common in all money situations for "How much did you lose in the transaction", i.e., "paid." And ending any sentence with the "to be" verb ("was") is very casual, but it goes well with "the damage" here.
  • dentist => tooth doctor -- just some humor, only someone so uneducated who literally does not know of the word "dentist" would use that :D (so don't you do it!)
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  • This is great explanations to me. Thank you, sir. I can see that so there's no need to say something like "how much you'll have paid," but could you add some words to confirm this a little?
    – karlalou
    Jun 30, 2020 at 2:03
  • I consider that phrase incorrect because that is mixing tenses. "You'll" = "you will" = future. But "have paid" = past. The only way that could work is if you setup a future-past up-front like this: "Once you are complete with your appointment, how much will you have paid?" That basically says, at a point in the time in the future after you paid, your payment will be in the past from there, so how much was it? This could be stated much shorter and more straight-forward like this: "How much will you pay?" But if you can't know that yet, you can continue with the original "tell me" statement.
    – wiigame
    Jun 30, 2020 at 3:24

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