I think the big thing to remember is that the meaning of something isn't the dictionary definitions of the words combined with the rules of syntax. If someone asks you what you though of a play, wanting to know what you thought of them, and you know this, saying "the acting was bad" is intentionally misinterpreting their question. It is an example of lying with truth.

Yes, understanding the question being asked is important.

"What did you think of the play" does not necessarily mean "what was your entire critical view of the play?" It could mean "what encouragement can you offer me?"

I would expect someone who presses me for an answer would actually want to know the answer, but maybe I just have bad social skills.

Alternatively, it could be the other person who made a failure of social skills: they sounded like they were pressing for your entire opinion, when they actually intended to be asking for encouragement, and they did a bad job of communicating what they wanted.