I kind of assume you can't, but can you deduct money that you gave to a homeless person on the street on your taxes? Just wondering. And, no, I do not believe they used it for drugs/alcohol so please don't bash me on that. I ran into a former child (now adult) that I knew when she lived in a group foster home. She was living on the street. I gave her $150 for a couple of nights at a hotel. I assume I cannot deduct it but thought I'd ask.
It's always good to ask if you're unsure. No, you can't. Only if it's given through an acceptable charity organization of which you would need a receipt, just in case you get audited. I'm sure you probably already know that though. That was a very generous gesture you made for this person. You may want to try and see if maybe an organization like Salvation Army or St. Vincent's would be able to help you with that expense. Otherwise, look forward to being blessed 100 fold. Take care.