Why should we do chessed to a frei person if they don’t deserve it? Why on Purim does it say “Anybody who sticks out a hand -we give them money”, the rest of the year we are allowed to look if they are indeed needing of Tzedaka? The answer is (that I heard), on Purim a lot of people ask for things from Hashem more than the rest of the year. The day is M’sugal for our tefillos to be answered. But Hashem always judges us up Midda keneged midda, what if we don’t deserve the thing we are asking for? Therefore, we don’t ask a person collecting Tzedaka on Purim if they deserve it -so when Hashem judges up on Purim -he will say midda keneged midda -just like that person didn’t look at the poor person before he gave him money to see if he deserved it -I’ll also not look at the person who is davenning to me to see if he deserves what he is asking for. The same thing with a frei person -if we don’t look at whether they are deserving of the chessed, but do it anyway -then when we need a chessed -Hashem won’t look at us to see if we deserve it!
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