Yes, I can relate. I realize now that fun conversation is highly illogical, emotion based. I view my desire for control and logic actually gets in the way of emotions, which makes conversations less enjoyable.
Me too. I feel that the key insight is that rational mind is almost always too slow to keep flow of the conversation interesting. It inevitably destroys timing and rhythm.
You can observe this clearly in stand-up performances - rationality of the bit is only minor part, the delivery is almost everything.