I don't think he understands BEFORE he speaks that what he is saying is really inappropriate and rude. I think he understands it afterwards. I love the idea of asking him to re-phrase it as a question.
Why is he making these comments? He has started wanting to converse, and is conversing with many adults. Many of these conversations are admirable. I'm impressed by his confident, long, "mature" conversation with adults, many times, ones he doesn't even know. I think his comments to the doctor/staff and speech therapist were partly outgrowths of this, just instances where he grossly missed the mark on appropriateness.
He also does have an older kids sense of humor, so the references to "middle school" humor may be part of it, where he thought he was being funny.
I have no problem with him sharing these thoughts and speaking his mind with me alone, and welcome that. We do talk frequently about people's judgments/perceptions if we use swear words (at least here.)
I don't view his intent as being more malicious than, at worse, "middle school humor."
