My only problem with this is that I'm not sure if he's acclimated enough to approach obvious non-baseline humans. (Or non-humans for that matter). As for trying and failing? He did not get to be as old as he is by failing at the victim selection process. I'm going more for pure Gothic Horror and less crack.

After he's in bar proper, we can try the crack (I suck at crack, tho', I warn you now.)

Does she ever go anywhere without the wings?