Hahaha, I like the combination here. 
The obvious choice for me is Kenny Omega - part of that is that he's just the wrestler I think would be the most fun to hang out with, and part is that he strikes me as someone who would make anything feel interesting. Could watch the most bland nothing show ever and it'd be turned into a spectacle. I think Willow Nightingale's probably close behind for similar reasons, although she'd be better to watch something actually good with, I think.
I do think it'd be really funny to pick, like, the least nerdy people in the AEW roster just to see the reactions, though. Like, we'll take Bryan Danielson, Taz... probably Excalibur too, just to make some sarcastic comments throughout, and put them in front of the most eccentric anime imaginable. That'd be a fucking blast.
All of this is probably absolute nonsense, but hey, fun nonsense to think about and write~ 
