he could be convinced ONLY ONCE to be a chill guy, but he'd also be like "what do i get in return?" which could lead to him convincing her to start a business in seattle. he'd want to invest, yknow? if every hundred years he comes back to settle payments with his supernatural "friends", he'd have such a lucrative little nugget of fortune purely based on her profits alone. plus, he'd be into the whole underbelly of her work since he's a being of chaos, and that includes chaotic sexuality