Can anyone relate to this communication problem?

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When I was a child my family would get irritated but also eventually found it amusing that in response to lots of what they thought were simple questions or instructions I would say: ‘but what do you mean?’

I will illustrate this situation with an example I have recently read in a book about autism (I don’t know if my problems are due to autism, but I am reading about it anyway):

In response to a question such as ‘what did you do over the Christmas holiday?’, the book explains that for many autistic people this question can cause anxiety and confusion as it is too open-ended. According to the book a non-autistic person would understand that to mean ‘how did you celebrate the holiday and with whom?’ Whereas someone with autism may wonder what details about their Christmas holiday to include: should they start from the beginning of the holiday and describe everything they did from start to finish?

For me, this accurately describes why I have problems with questions like that, and also illustrates what I meant with my frequent childhood ‘what do you mean?’ question. Taking the above example, as a child I would have responded ‘what do you mean?’ to someone asking me what I did over the Christmas holiday, because I thought by asking ‘what do you mean?’ they would then elaborate on which part of the Christmas holiday they are asking me about, and whether they want me to describe every detail, or just some.

However, now I see why my question got irritating to people; because as a child I had assumed they knew what ‘what do you mean?’ meant. It meant: ‘what do you mean, exactly?’ So I got frustrated as they would act like I was acting stupid, and I got frustrated because I thought they were acting stupid But as I got older I learnt to get the information I needed to answer their question by asking more pinpointed questions, e.g. I guess with the Christmas holiday question instead of ‘what do you mean?’ I’d say: ‘Do you mean; what did I do for Christmas day?’ (although even narrowing it down to Christmas day I still struggle to answer that question as I struggle to formulate an answer spontaneously when faced with a person in real time waiting for the answer, unless I have pre-prepared the answer due to knowing that that is a small talk question I am likely to be asked around that time of year).

I think as a kid I would also use the ‘what do you mean?’ question when I was confused about WHY someone was telling me to do something. E.g. ‘Be quiet!’ I was fine with being quiet as long as I knew why I had to be quiet, but if I didn’t know why I had to be quiet the demand on its own confused me. However ‘what do you mean?’ in response to a simple demand like that, didn’t go down too well. I guess I was also both too young to use more descriptive language that would better communicate what my problem with the question or demand was, and too young to realise that the problem was a communication problem.

I wondered if anyone here has had any similar experiences?

Are you reading The Complete Guide to Asperger's Syndrome by Tony Attwood. Those type of questions are mentioned in this book.

I wouldn't have a problem understanding that question but some questions do baffle me and I have to ask for clarification. And, yes, people do get irritated with me, roll their eyes, make fun of me or whatever. I really don't know how to handle it.

I relate to that, yes.

Yes. I get worse about it when I'm tired or overstimulated.

It is a relief to hear that other people can relate to this,

yes all the time, people will ask questions and not really care and I don't like it. When I try to tell people stuff and they cut me off, so now I do ask for clarification.

NT people often are unclear or dishonest in their questions - the biggest is "how are you" they only want to hear "fine" or "ok" and about weekends or holidays they really only want to know "I had family over" not much more in most cases.

yes
always
every day

Yes

I feel incredibly uncomfortable with any question that is not a direct question. I am finding at my current workplace that people's regular greetings make me feel incredibly nervous. I think it's because I don't know how to respond to them.

I found that I tend to win people over by countering this awkwardness with an outgoing personality and a lot of energy, which helps mask it somewhat. Still, feel really uncomfortable and want to put my head down when people randomly smile at me and be all polite. I feel pretty bad about it honestly.

I've found that the answer: "Oh, you know," seems to completely satisfy their curiosity.
Then they get on with talking about whatever they had originally wanted to before artificially initiating a "conversation" trap.
Saves time all the way around. I don't have to figure out they're asking, they don't have to pretend caring or interest, and I don't feel stoopid for over-thoroughly answering a perfunctory question.

Most of the time it's just a conversational crowbar because they just want to do all the yapping.
It's pretty normal. It doesn't hurt my feelings, nor am I angry or bitter about it.

As long as they're talking I'm 99% less likely to socially f*ck up the convo.