... I am not sure how to create such responses without losing some appropriateness for cases where the other person doesn't want to give details.

Yeah, that's the problem. I have no solution, I'm afraid, other than to know the person you're speaking with, and being able to predict what they prefer based on your knowledge of their personality.

As for Captain Awkward... I'm having a hard time verbalizing the reasons for my distaste... I will maybe read a post or two and see if I can elaborate/explain my view.