>In summary, I find a lot of what makes a good conversational isn't following arbitrary norms of the era, but a strong empathy/understanding for the emotional effect of every topic and bouncing between those emotional states with grace.

I think the problem is that norms actually encode this information - it's not just empathy and understanding, it's empathy and understanding that is appropriate as per the zeitgeist. The normal range of responses is entirely defined by local culture and not only is this the kind of implicit, abstract set of ideas that autism can make difficult to learn, but this discussion itself is also a social grey area which is only appropriate with a minority of people; and then only if they're already familiar and comfortable with you.

When you lack internal boundaries, it is difficult to navigate those of others when they are not communicated to you explicitly.