OK. This one is a bit unusual, so I don't want to tell you what to do. I will observe that it appears that there have never been any formal business agreements or loans between anyone. Thus, it appears that you gave a gift to your friend when you supported him. Assuming that your friend is under no obligation to you, I don't know of any law that prevents your friend from giving you a gift. The 2018 gift limit is $15,000. The receiver of a gift does not pay taxes on gifts. The giver should file forms if the gift limit is exceeded during the tax year. The gift can be given with no paper work if below the gift limit. Next year, he can give a gift again. So that's the technical observation. I can't help but to also observe that paying the high sum of money out of SSI does not seem reasonable for someone who is getting government support due to having to live on limited means. Please think this through and be fair.
