Whoever is generous to the poor lends to the Lord,
and he will repay him for his deed.
The lesson of this proverb is not about how to place God in our debt and make him give us what we want. It is about caring for the poor. It shows the compassionate heart of God for the poor, what we often lack.
We want to see a return for our money. We want to be assured that the poor will spend the money wisely. We'd prefer a background check. Did this person become poor out of circumstances beyond his control or did he contribute to it by his behavior? If so, what is he doing productively to get out of his situation? Will he be asking for more money?
Generosity to the poor is more than giving money. It is taking time to treat them as people precious in God's sight. It includes treating them with dignity. To be generous means to go beyond what is convenient and to give of ourselves as we would to those close to us.
Remember, the poor represent outwardly our inward condition before God who was and is generous to us. He already pours out his riches in Christ, not because he has ascertained we are a worthwhile investment, but because he is generous to the poor.
It is true that we should give wisely and give in a way that helps. But don't let that become an excuse to be cold-hearted and to resent the poor. Be generous in deed and in spirit.