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I'm having issue determining whether to use conditional or subjunctive or both.

I understand that conditional is a tense while subjunctive is a mood, but I still have trouble with usage.

To my understanding, subjunctive is for verbs in which someone's will is being imposed on another or some kind of judgement/uncertainty, while conditional is used for hypotheticals and would/could/should's.

So what would I do for a sentence like "I wonder if you would do that?"

Doesn't the "wonder" express uncertainty while the "would" aligns with conditional?

Sorry if I'm not understanding this correctly and thanks in advance!

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The problem is that your premise "subjunctive is for verbs in which someone's will is being imposed on another or some kind of judgement/uncertainty" is oversimplifying. According to that, in the sentence I wonder if this is possible "is" should be a subjunctive in Spanish. However, you can say any of the following:

Me pregunto si es posible.
Me pregunto si será posible.

But what you cannot say is:

Me pregunto si sea posible.

Using the subjunctive in the last example is ungrammatical, and yet the uncertainty is clearly there. Your premise should work in most cases, this is just one when it doesn't. There are basically two principles working here:

  1. "Me pregunto" only takes verbs in indicative: me pregunto cuándo vendrá / dónde está el dinero / si es una buena idea / quién vino a la fiesta...
  2. Conditional forms only exist in the indicative mood.

Therefore, "I wonder if you would do that" is:

Me pregunto si lo harías.

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Think about conditional + subjunctive as conditionals in english:

If I were you, I would spend all my money!!!

Si yo fuera tú (subjunctive), ¡¡me gastaría todo el dinero!! (conditional)

The subjunctive depicts some unreal, hypothetical case; the conditional completes the subjunctive clause extending and completing the sentence.

Realize that in the previous sentence the conditional ("me gastaría todo el dinero") does not make sense by itself but when it is enclosed together with the subjunctive, completing the sentence.

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The thing is that we have a different modal verb for many expressions , you can look this up and be confident at the time of speaking, " many and just many of the times you guys use WOULD in English, we use COULD in spanish.. check it out on the internet and when you have already mastered, you will sound super natural.. Thanks.

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Sounding natural is the key to a real high level in any lenguage, as spanish speaker I can tell you that most of the spanish lenguage is used the same way in all spanish speaking countries, we have different idioms , sayings, slang ect ect but, the main content of the lenguage is basically the same. I ignore if this happens in English too. This is the natural way to say it in spanish : when you are asking for a favor , you can always say " 1 ME PREGUNTO SI PODRIAS HACER ESO POR MI", 2 ME PREGUNTO SI PODRIAS AYUDARME CON MI TAREA.. WHEN YOU ARE TRYING TO INVITE SOMEONE to do something for fun , we always say= ME PREGUNTO SI QUISIERAS IR CONMIGO AL CINE, 4 ME PREGUNTO QUE TE GUSTARIA HACER HOY.. your sentence I WONDER IF YOU WOULD DO THAT is perfectly correct, but we normally use it in a more intense way e.g. I would die for you.. I wonder if you would do the same for me .. yo moriria por ti, me pregunto si harias lo mismo por mi.. if you use these ways, you will sound like a native speaker..

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