Jon Bloom (Executive Director of Desiring God) has recently blogged two entries on the subject of Jesus’ command in Matthew 5:42 (“Give to the one who begs from you, and do not refuse the one who would borrow from you.”) I recommend reading both of them.
When I think about this topic, I always recall Dale Ahlquist’s description of G.K. Chesterton in his book Common Sense 101: Lessons from G.K. Chesterton.
He seems so frivolous and so careless, but he gives money to beggars, not frivolously or carelessly, but because he believes in giving money to beggars, and giving it to them “where they stand”.
He says he knows perfectly well all the arguments against giving money to beggars. But he finds those to be precisely the arguments for giving money to them. If beggars are lazy or deceptive or wanting a drink, he knows only too well his own lack of motivation, his own dishonesty, his own thirst.
He doesn’t believe in “scientific charity” because that is too easy, as easy as writing a check. He believes in “promiscuous charity” because that is really difficult. “It means the most dark and terrible of all human actions—talking to a man. In fact, I know of nothing more difficult than really talking to the poor men we meet.” (pp. 13-14)
I have given money to someone with a sob story, and afterwards concluded that I was scammed. I have given a few bucks to someone in need, and afterwards regretted that I didn’t do more. I have spurned a beggar’s request, and wondered if I did the right thing.
The thoughts from Jon Bloom and the example of Chesterton convict me that it is better to give than to worry about analyzing the situation and attempting to predict the outcome.