@Ragman,
Meantime, did I read he is 33? Being 33 and not savvy about relationships is not the end of the world, and being 33 and too savvy isn't either, but there are differences.
My take on this is that your fellow has little perspective, quite possibly not his own fault. I've no idea how to clue him in. I, finally, do not think this is something you need to fix, except that you carried him along when you didn't mean it, which is basically mean. Stop that.
Ooh, not directed to you, rags.