So this year he is being grade accelerated and once again I am struggling with what to do. As soon as the mom asks me what teacher he has it is going to come up and again by akward. I want to bring it up so it isn't as weird but just not sure how to do it. Any ideas?
So, he's skipping a full grade not just subject accelerating again, right? I don't know that you did anything wrong with the last occurrence in that I don't see any reason why subject acceleration needs to be mentioned to other parents. My dd11 is taking Algebra I next year, as are a number of other kids in her grade, but I'm sure that there are friends of mine, family members, parents of kids with whom she attends school, etc. who still do not know that she is subject accelerating in math even though she did last year as well. I'd agree, though, that grade skips tend to be so obvious that you won't be able to keep in under wraps and you probably should let friends who will find out anyway know.
Like I said earlier up in the thread, I don't think that my trying to avoid telling people when dd13 skipped 5th worked out too well and I'd probably do it differently now even with people who are insecure and likely to get defensive or hurt. I'd probably take one of two approaches:
1) approach the mom and tell her that you realize that last year you didn't handle it well when you didn't tell her that your ds was subject accelerating in math so you wanted to be the first to tell her this time that he will be in a different grade in the fall than expected. I'd stress here that the school approached you (if that is true), that there was an evaluation process that looked at a lot beyond ability and achievement (in case it sounds like you saying that your kid is more able or a higher achiever), and that you hope that he is able to find friends in his new class and very much value the support of the friends he holds close now.
or
2) I'd wait for her to ask about his teacher for next year and then go into essentially the same spiel.