Butterfly - he asked b/c he had nothing to lose by asking you as there are so many tourist that do end up sending money. I think I would just choose to leave him alone as he has ulterior motives. There are enough drivers that you can hire and like you said separate friends from business.

I have a small group of friends in Negril that I easily call friends. They have never asked for anything and I don't have to pay for them for anything. One of these friends is also our driver but I do make sure to pay for that as it's only fair. Then there are those people that are "friends" that ask for everything. As soon as they see my cooler on the beach they are quick to ask for a beer or bring an empty cup for something to drink. The first few times, I don't mind sharing but they seem to come around all day every day. I'm trying to still figure out how to put a stop to it without completely cutting them off from me sharing with them.