I've definitely also had conversations where the guy in the room who was the most confused and having the least fun was the one with the most book smarts.

Isn't that what you would expect for most conversations, when all else is equal?

... well, it isn't what I do expect, so I guess I wouldn't. The thought never crossed my mind, so I don't really have anything more insightful to say about it yet. Let me chew on it.

I suspect that I mostly socialize with people I consider equals.