I have in mind the sort of situation where someone really needs to know some information even though it will hurt them – an obvious case would be a doctor telling a patient she has cancer. Another case would be a teacher giving an honest evaluation to a student that hurts the student’s feelings, even though the student needs to know the information to correct her errors (this may be especially tough on good students – it’s happened, I suppose, to all of us, but it’s the teacher’s job).

Also, there are people (probably all of us, at least sometimes) who “get their feelings hurt” simply because someone else expresses a different opinion. That can be a way of bullying people to force them to agree with us, and I don’t think anyone is obligated to avoid hurting our feelings in such a situation.

I think that gratuitously hurting other people’s feelings – just for the fun of it, so to speak -- is pretty much always wrong.