I just wanted to add that when DS6 was in K last year we had some social issues as well and I have a slightly different thought on what was going on. I don't really think it was "immaturity" as everyone seems to immediately assume. I think, instead, that it was a situation where DS was functioning at a different cognitive level that his classmates yet really really wanted to be in their "group". His reaction was to try to copy what he THOUGHT they were doing. To a kid who is much more interested in reading about the solar system than crashing cars it can be hard to interpret the behavior of others in the class. He would watch the kids around him roughhousing but when he would try to join in it would just be 'wrong'. When he would try to do what he thought he saw the other kids doing it just came off as awkward. As the year progressed he did get better at mixing with his multiple groups of friends (anywhere from K to Grade 3)but even now we have many conversations about being confident in one's self and not trying too hard to "be like" those around us. When he is just himself (albeit sometimes a toned down version of himself) he is much more comfortable in his own skin and it shows to those around him.
Yes, we've had this problem for many years! DS10 has gotten better at recognizing what others are doing and being able to join in, but it's still a struggle sometimes.
My heart breaks for your little guy, too, asking all those questions about what is "wrong" with him. I get those questions at bedtime sometimes, and just have to walk away after a while because it's just too much for me to handle. I can't stand that he feels that way, and I can't stand that he can't understand the answers I give him, and I have to just go away and cry. It's so hard for them.