Western Union is an expensive but reliable option. The receiver doesn't even need a bank account.
If you want to send money do so, as long as you're not impoverishing yourself....which I assume is unlikely. You hold all the cards; if the guy is looking exploit you, don't answer communications. If he is appreciatve then good; you have, in Buddhist terms, made merit and this will affect your passage through this life into the next.
Apart from my partner, I can think of three recipients of my largesse over the years. I have no regrets: none of them harassed me for extra donations.