“Will he nill he…” huh, I wonder if that’s the etymology of the modern expression. “Willy-nilly” just seems like a nonsense phrase. “Will he nill he” could be read as “will he or will he not,” right? It seems like only a couple short conceptual hops to go from “whether or not he decides to do something” to “look at all the random things he could do.”

I largely agree with you, but I can imagine a scenario where there is some connection to "Will he? Won't he?" semantically.

> Will he nill he…” huh, I wonder if that’s the etymology of the modern expression.

Well, that's at least what the internet told me, last time I checked.

I suppose I should have looked it up! For some reason I just looked up the definition of nill and tried to work out a plausible folk etymology from there.