Asking clarifying questions is not always socially acceptable! Then what?

Some random things that seem difficult to get an AI to deal with:

1) Things that people expect you to know by observation, but not be told and not to say.

2) Things that people expect you to know/adhere to, in spite of being told something different.

3) Strategically creating the impression that you do or do not have the ability to change your course of action.