Compare this

The last one is why I asked you if you were proud of what you did, and why I'm perplexed you took it as a loaded question.

With this

I would most certainly not be proud of having failed to impart my superior understanding to a member of my community who was suffering as a result of lacking that understanding.

This seems like you were going to make a negative judgement if he claimed pride. Thus the question does seem loaded. Pride is one of those thing that it is not a good thing to be fairly often.

It might well be Rain thinks that you had the same sort of problems he did(?) and was taking steps that would have helped him. But for whatever reasons they don't help you.

Also try not to take karma loss too personally. It also signals to other readers of the site what is good or bad. It is simply a number in the database.