Unless HD has a romantic angle, I reckon his next move is to figure out how to recover his investment in that date, whether directly (or more likely) indirectly. If he's in it for the business, either a price quote for future services will be forthcoming or he's setting up a kind of sugar daddy/investor/creditor thing, maybe even some kind of extortion. I agree with William M., be careful. The mindf--k thing is potentially perilous, and it seems already effective.