At weddings, there can be so many people collecting that if I gave five dollars to every person who asked I would be giving out 80 to 100 dollars in tzedekah. After a point, I just shake my head, and say, sorry. Since the people collecting saw me give to others, they know I have reached my limit.
As for those you see on the street, I caught one guy standing on the street with a crutch. When he asked me for money, he didn’t realize that I had seen him get on the same train I took, but then in perfect health. I thought at the time he was returning the crutch or bringing it to a friend. Now, he was coughing and leaning on the crutch for support. I couldn’t resist saying, “Aren’t you the guy who got on at such-and-such stop around 10 am?”
I do think that there is merit to not subjecting a request for money as if I was a loan officer in a bank. A dollar here or there to someone who might be undeserving is not worth my time or trouble to cross-examine them. A dollar I give to someone willingly is counted in my merit whether the man or woman is a phony or not. Hopefully, it will also set aside harsh judgment later on.