I think I am the only non-literal thinker in our house, so I can relate.
My kiddo does like nuance in jokes, but he doesn't pick up on nuance in social situations, directions, or body language. My daughter bought my son a season of Big Bang Theory, and we watch the episodes together. I tell him why people think a certain situation is funny, what was the expected behavior, etc. Believe it or not, it opens up conversations. There are some adult relationship overtones, so I don't know if this would work for you, but with two college-age siblings, it is nothing my son hasn't seen or heard.
I'm looking forward to reading suggestions as well. Teaching someone else to discern and pick up on nuance is nigh unto impossible.