I'd like to add one more thing, in that if you're really trying to help, consider expose him to some NLP. NLP got a bad reputation from the people in the self-

I'd like to add one more thing, in that if you're really trying to help, consider expose him to some NLP. NLP got a bad reputation from the people in the self-help industry that latched on to it, but at its core it's about modelling thought processes (N) and language (L) to try to identify a sequence of repeatable steps that will consistently achieve a desired result (P). In essence it's a pretty good attempt at creating a functioning, logical, model of everything an Aspie doesn't intuitively understand.