I hadn't really made the speculations you make here about how Obi-Wan first met Dex, instead mostly thinking this showed Obi-Wan had become better able to seek out other viewpoints since The Phantom Menace. (On the other hand, I was also ready to suppose his line in this scene that "if droids could think, there'd be none of us here" meant he still had some unconscious prejudices.)

Your alluding to this scene at the end of your last post did get me thinking about the very line you quoted here, and in thinking about it I found myself wondering about "the difference between knowledge and... wisdom" as illustrated in those fans who can provide the "official" name, species, and biography for every alien in the cantina, but who don't quite seem to enjoy the actual movies as opposed to the hypothetical case they built up from The Empire Strikes Back... I've been willing to suppose I wasn't that far away from that once upon a time (save for some inarticulateness of my own that it just didn't feel satisfying to be dissatisfied with Return of the Jedi like so many other people), and I can recognize how narrow the path that took me to where I am now was. I have seen a few people proclaiming that male fans only "memorize" whereas female fans "create"...