Reader: I recently came upon a shiur about a concept that was knew to me. The idea that it can be viewed as some kind of evil if you give tzedaka to the wrong person, something to be punished for. Can you shed more light on the matter as it sounds a bit scary.
Rabbi: I don't know of the idea you cited, but Rabbi Chait discussed how lost money can be considered tzedaka. If he doesn't give tzedaka willfully, it will be taken from him:
"The gemara says that if one does not give Tzedaka, God takes that money from him. He may not even know how God does this. But despite this, it is still considered as if he gave Tzedaka. This is because through losing his possessions and his realization that his loss was due to his failure to give Tzedaka, it is considered Tzedaka because the person broke his emotion [his attachment to his money]."
Reader: How far does one have to go to verify if the recipient is deserving?"
Rabbi: Rabbi Chait said if someone asks for tzedaka, he is a suitable recipient. My understanding is that as personal dignity is a powerful need, if one forgoes his dignity by seeking charity, one's need for money must be even greater than his need for dignity, and thus, he is worthy of receiving it.