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I am learning to make sentences.

I find the form of Q&A quite useful.

So I think of an answer as to "I guess he thought that was pretty awful".

then I come up with different questions below.

It occurred to me these are messy questions and are different to some degree.

They look similiar.

Are they correct?

What are their differences?

What their answers would you provide?

Thank yout for reading my questions.

Que1.

Did he think that was pretty awful?

Que2.

How did he think that?

Que3.

How did he think that was pretty awful?

Que4.

Do I guess how he thought that?

Que5.

Do I guess how he thought that was pretty awful?

Que6.

How do I guess he thought that?

Que7.

How do I guess he thought that was pretty awful?

Que8.

How did he think about/of that?

Que9.

How did he think that like?

Que10.

What did he think about/of that?

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Que1.

Did he think that was pretty awful?

This is grammatically correct and I can imagine a scenario where someone would say this but, if she did, the answer would be different than the one you provide. The question ehre is asking Did he think which invites a simple yes or no answer. It would be redundant for someone to completely restate "I guess he thought that was pretty awful". Instead, they would confirm simply by saying:

I believe [so / that he did].

In order for the question to invite an answer like "I guess he thought that was pretty awful", the question would need to be more open-ended (see your question 10) and not imply a quality of emotion to begin with:

What did he think of that?

I guess he thought that was pretty awful.

Que2.

How did he think that?

I think this technically is grammatically correct but would never be said in practice. We know how people think things (they use their brain) so you would ask instead:

Why did he think that?

But this question is asking for a different kind of answer than the one you start with. Your starting answer is describing the person's emotional reaction to something. The question(s) above are asking for the reasons he had that reaction.

If you wanted to use the word "how" to elicit the answer you provided, you would ask

How did he find the [person / place / thing]?

In this example, the word "find" means "become aware of" not "to locate."

How did he find going on the roller coaster?

I guess he thought that was pretty awful.

Note that, because your answer uses the word "that" instead of "it," we're referring to an action or event rather than an object (and certainly not a person). Because of this, the first person would need to use an action/event in order for the answer to need to use the word "that." This is why, in the example above, the first person would say "going on the roller coaster" (a gerund) and not simply "the roller coaster."

An alternative would be this:

How did he find the roller coaster?

I guess he thought it was pretty awful.

Also note that you could use "how" at the start of the sentence using "like" to form a more slang version. This is because the word "how" isn't entirely necessary and invites the answerer to reply with greater detail than simply saying yes or no:

Did he like walking to work?

Yes.

Compared to:

How did he like walking to work?

I guess he thought that was pretty awful.

Que3.

How did he think that was pretty awful?

The starting answer is a statement that the person in question found something "pretty awful." This question is asking why the person found something pretty awful. If a person asked the question above, she would not receive the answer "I guess he thought it was pretty awful." Instead, they'd receive and explanation or list of the reasons he thought it was awful.

Also note that, regardless of how the question is formed, the asker would not say "pretty awful" with one exception: It is possible that the asker believes it is likely that the person found the thing quite disagreeable.

To verify that this is indeed true and to confirm the degree to which the person found it disagreeable, the asker might form the question as a statement of fact and seek to elicit a response from the second person by appending a questioning word like this:

I guess he thought that was pretty awful, huh?

In this case, the answerer would not repeat the full sentence. If the answerer also thought that he thought it was pretty awful, she would simply say yes or no.

Que4.

Do I guess how he thought that?

This would never be said. The phrase "Do I guess ..." might be said by someone if they are asking if they are expected or required to make a guess about something but this would be a slang form of what would properly be written "Should I guess ..."

When asked, it would lead someone to confirm if the asker needs to make a guess about something. It would not lead someone to provide an answer like the kind you start with.

Que5.

Do I guess how he thought that was pretty awful?

See question 4.

Que6.

How do I guess he thought that?

The only situation I could imagine someone saying "How do I guess ..." is if they are playing some sort of videogame and they do not know what button to press to show that they want to put forth a guess on an answer. Outside of this very specific situation, it is just a really weird clause/sentence.

Que7.

How do I guess he thought that was pretty awful?

See question 6.

Que8.

How did he think about/of that?

See question 1. You would not say "How did he think about that?" but you could ask "How did he think of that?" However, this is asking a fundamentally different question than one that would produce the answer "I guess he thought that was pretty awful." If you asked this question, you would get an answer that talks about the thought process that resulted in an idea.

How did he think of that?

Well, he doesn't want to throw out all his old shirts. I pointed out that we need to replace our worn out blanket so he suggested that we turn his old shirts into a new blanket.

Que9.

How did he think that like?

This is grammatically incorrect. It almost seems to be asking this:

How did he like that?

In this case, see the notes on Question 1

Que10.

What did he think about/of that?

Ding ding ding! This is perfectly correct (using either about or of). It is grammatically correct and is exactly what someone would say or write. It would also lead someone to reply with your original answer.

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  • Wow, I could not imagine a better answer than yours. Thank you. – Stats Cruncher Apr 21 '20 at 20:52

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