Someone borrowed $500 dollars from me a while ago and I know that they don’t have the means of paying me back. Can I deduct that money from maaser money that I would owe and then forget about what they owe me?
Although there are Poskim that say you can do so under certain circumstances, the majority of the Poskim are of the opinion that it cannot be done retroactively.
As a general rule, if its a loan which can reasonably never be retrieved, it is no longer considered Tzedaka.
ראה הרמ”א סי’ רנז סע’ ה, השך ס”ק יב, והפ”ת (ס”ק ה מסי’ רמט ס”ק א) מביא דעת הנוב”י, אג”מ יו”ד ח”א סי’ קנג, תשובות והנהגות ח”ב סי’ תעא, צדקה ומשפט פ”ה הע’ נ, שו”ת משיב דבר יו”ד סי’ מט , שו”ת מנחת יצחק ח”ה סי’ לד ס”ק ח ובתו”מ חכ”א ע’ 234 הע’ 183.
I can ask them for it, it will just be very hard for them to pay it back. They would if I really wanted or requested. But obviously, it’s much easier if I don’t, because I know that they don’t have so much money.
As mentioned, if you didn’t intend to do so originally, you cant do so now retroactively, However, if the loan is still collectible, you can ask permission from the poor borrower to give Ma’aser money to the third party on their behalf. This money can later be used to pay up the loan.
See the Hebrew references here which are related.