[coldtea]

Not so sure about that. You also have to "have it" in you in some deeper subconscious way, not just rationalize what you should say.

The same way a shy person can read about the actual best ways to approach a romantic interest, but not be able to convey it realistically enough.

Why would this be a problem for an AI? Well, if we imagine a powerful thinking AI, I'd also attribute it with having emotions, subconscious (e.g. hidden weights in its neural network brain, etc), so this would also apply to it -- can't see why it would have to be a total "sociopath" (which for humans comes from some kind of genetic or environmental accident).

Besides, while you can "contemplate about every sentence and somehow compress that into 1 second", actual "trial and error" with humans cannot be compressed.