C.S. Lewis's stepson Douglas Gresham tells the story of Lewis and a friend walking along the street one day when a beggar approached them asking for money. Lewis's friend kept walking, but Lewis stopped and emptied his wallet, giving the beggar its contents. After rejoining his friend, he was chastised. "You shouldn't have done that, Jack. He'll only spend it all on drink." Lewis joked, "Well, that's what I was going to do."

The situation is a common one and ages old. We are no more faced with beggars today than the disciples were in the first century. In urban settings or rural, the specific approach and contexts may differ, but the neediness and the opportunities do not. What is your response when a stranger asks for money?

You are walking down the street or pulling out of the grocery store parking lot and you are confronted by a haggard figure, perhaps holding a sign, perhaps telling a familiar story about being homeless or hungry or needing to travel to a certain location or having a car out of gas. The stories can be eerily similar. I've heard the "I'm trying to get to _______ but don't have money for gas" story quite a bit. I have offered before to go to the gas station and put gas in their car. Sometimes they agree. Sometimes they don't. I have offered to get food instead of giving them cash for food. Sometimes they agree. Sometimes they don't.

Let's make the options simple for the sake of the gist of the argument. A hand is outstretched before you. Do you put money in it or do you decline?

Most of us at that point begin to measure up the man (or woman) before us. Do they look honest? Do they look authentically "down and out?" Do they look like an alcoholic or drug addict? Then the street smarts kick in. They will probably just spend it on alcohol. I am probably just supporting their drug habit. If they put just as much energy into finding a job as begging for money, they wouldn't be in this situation. If they weren't so lazy, they wouldn't have to suffer this indignity. By giving them money I'm just enabling them, not actually helping them.

The street smarts—based on assumptions and presumptions, not actual knowledge of the person—are thinly veiled justifications for not helping. They help us feel better about saying no.

What does Jesus say?

The Sermon on the Mount is so impractical. So inefficient. If you were designing a religious system for maximum ease and self-actualization, this would not be it. The whole thing seems designed to make its adherents "get taken" left and right. Somebody asks for my coat, and I give them my shirt too? Somebody asks for a mile, and I go with them two? Somebody hits me, and I offer them my other cheek? This isn't only not street smart, it isn't even common sense. Jesus is asking us to put ourselves in some very vulnerable positions. And in Matthew 5:42, he says:

Give to the one who begs from you, and do not refuse the one who would borrow from you.

Immediately we begin thinking of all sorts of loopholes and footnoted caveats to explain that this doesn't mean exactly what it says. And maybe some of those caveats are right. For instance, if you know someone's going to waste money on an addiction, not just suspect they are, it's probably wiser to give them another form of help—a meal, loving counsel, a friendship. We only ought to take care that our refusal to give what is being asked is based on facts, not imagination, and is not the "plausible argument" we're using to justify our disobedience to a pretty clear command that comes with no asterisks. "Give to the one who begs from you."

Is Jesus smart? Does Jesus know the way the world actually is? Can he be trusted in this moment to give us sound counsel?

Here's what I think Jesus wants us to do, and our response to a beggar gives us the opportunity to do it:

1) Hold our money loosely. I think that's what Lewis was getting at in the exchange with his friend. He was comparing the beggar's suspected frivolity with his own known frivolity. Only in the economy of self-justification is my frivolously spending $3 on a coffee deemed more virtuous than, by presumption, a beggar's frivolity.

2) Trust him with people's sins. Maybe that person will squander what you give them. It's not our job to manage the expected sins of others. It's our job to be faithful to God, obedient to his commands. So the better hedging of the bets here is to give out of obedience and trust the beggar's financial management to the only God who judges the living and the dead. Let us give, and let us let the Lord sort it out.

In one of his Letters to an American Lady, from which we get another version of the "spend it all on drink" story, Lewis writes these other pertinent words on giving to beggars:

It will not bother me in the hour of death to reflect that I have been "had for a sucker" by any number of impostors; but it would be a torment to know that one had refused even one person in need.

No, it's not street smart or common sense to give to those who ask of you, but it is wise. Very, very wise. It is wise to obey Matthew 5:42 with as few loopholes as you can attach to it because doing so says you obey God, not your suspicions, and you hold your money loosely because God is your God, not money. What you do with your money bears witness to what you worship.

I was had for a sucker last week. I felt pretty sure I was even before I knew I was. I was not surprised later to find out I'd been had. I had reminded myself of Matthew 5:42 in deciding to give the money out, and I reminded myself of Matthew 5:42 after I realized it was a mistake. I should have helped in one of a variety of other ways. Only God has 20/20 foresight. But it wasn't just Matthew 5:42 and the Sermon on the Mount's kingdom ethos in general that got me. It was this:

I picture myself as I truly was, apart from Christ, in the light of God's holiness. Unclean, undesirable, unjustified. A beggar. Jesus could have taken one look at me and come up with infinite excuses not to help. In fact, because he is God, with the omniscience of being God, he didn't have to presume or predict—he knew that throughout my life, even after salvation, I would waste his grace like the prodigal moron. And yet, unhesitatingly, eagerly, with all the love of him who is Love, he gave me no mere pittance, but lavished on me the immeasurable riches of his kindness and mercy, united me to himself in spirit, and guaranteed for me the inheritance owed himself. Try being stingy and common-sensible with that reality crowding out your brain.