New Out of Character Thread
It seems to me that Skyrah is cultured in the sense that she has been exposed to, and even participates in, the arts; a sort of intellectual or academic culturization, whereas the type that would actually make this particular mission easy is more being inculcated into civilian (or at least non-regimented) society. It really doesn't seem that is where Skyrah is at, especially given that she's showing up to vacation in uniform. ;)
Michelle seems the best at that sort of thing, and Thirteen the worst (since he has no memories of doing anything even remotely like that; it isn't part of his training). Still, I suspect letting her hair down, being vulnerable, letting others in are all a pretty big ask from Skyrah; to some extent or another, all that comes naturally to someone who grew up a civilian (like most everyone), or has spent lots of time around civilians (like Korvan, and any other normal Zents).
Of course I could be totally wrong about how you see Skyrah, and she is your character, after all. Either way, it should be interesting!