Thank you. I don't actually call him shy. I titled the thread that and probably shouldn't have.

My son is in a math program taken at our local university and I think that helps as it is taught much more like a college course than an 8th grade math class.

I guess I am just looking for suggestions to build confidence and bring him out of his shell a little. There is obviously nothing wrong with being introverted and it provides him many advantages. While my story is not his, I firmly believe that being put in more situations to build self confidence would have been a huge benefit for myself.

He struggles with anxiety and this is probably the root of the issue. The perfectionist trap is something we deal with in every aspect of his life. As much as I love that he is so into grades, colleges, etc, I do want him to enjoy his time as a kid too.

When I watch him talk with grandparents and other adults, it isn't that he doesn't have anything to say, it's more like he struggles with the act of conversation.