“Should I give money to panhandlers/beggars?”

This is a question I’m asked often, usually from someone with a generous heart who has had a negative experience with giving.

It’s a complicated question.

Many of us have interacted with the man or woman who just needs $14.27 to pay for a hotel stay or a bus ticket back home. Maybe we give the 15 bucks, or maybe we don’t, but the interaction makes us feel somewhat icky. Because we are fairly certain that the beggar is just trying to score cash for drugs or alcohol.

Some of us, on the other hand, have interacted with someone who wants five dollars for food. We don’t have cash, so we offer to buy him a burger and he says, “Oh wow, that would be great. Thank you so much!”

Again, it’s complicated.

I know a homeless guy who begs for money every day, usually making between 30 and 50 dollars. After finishing a day of begging, he walks for miles to buy a drug called spice. He gets high every day and does not intend to stop using drugs.

He told me his homelessness is due to bad luck, not his drug habit.

I got to know this man over the course of a year. We have honest conversations about drugs and Jesus. He told me that when he was a toddler, his father was murdered right in front of him. He’s aimless and has no family. All of his “friends” are drug addicts.

Complicated.

So what does Jesus say about this?

“Give to the one who begs from you, and do not refuse the one who would borrow from you.” (Matthew 5:42, ESV)

That’s pretty straight forward, right?

Jesus says to give, but doesn’t say to give people whatever they want.

Maybe we get to choose what we give.

Let’s make it more complicated and look at that verse in its context.

This verse is the final thought in a teaching that begins with, “Do not resist the one who is evil.” (V. 39)

It’s the same passage where Jesus says to turn the other cheek and go the extra mile.

The context is mistreatment (aggression, greed, laziness). And in this context, Jesus says to give to those who ask.

So what? We should give cash to drug addicts?

A funny thing happened as I got to know my homeless friend mentioned above — He never asks me for money.

In fact, one of his fellow beggars recently asked me for money and my friend interrupted him and said, “Don’t ask him, he’s not the type.”

I took it as a compliment.

I work with poor, addicted people every day of my life and I am rarely asked for money.

Isn’t that odd?

Maybe the best way to solve this generosity dilemma looks less like analyzing the words of Jesus and more like friendship.