I’m going to assume the loan was not to a parent or your children or grandchildren. Any of these relations I wouldn’t ask for the money back or make a loan to begin with, it would be a gift, except in some sort of very specific circumstance.
We once loaned $15k to a family member and wrote up a few sentences on a paper stating the minimum payment each month to pay it back. No interest. We bothered to write it on paper, because we knew the family member sucked at paying debts. We gave them the money because his spouse seemed to have integrity with debt.
I told my husband if they don’t pay it back I will NEVER give them money again, but I also won’t change my relationship with them. His family tends to cut people off and estrange themselves, I didn’t want to do that.
Most jellies say the person you loaned the money to probably doesn’t remember they owe you. I think they do. They probably think you have plenty of money, and decided you don’t need the money to make themselves feel justified in taking your money.
If the money won’t make a big difference in your life, since it has been so long, probably don’t say anything, but I have to admit I can understand when the right opportunity came up I can see saying, “are you ever going to pay me back the money you owe me?” That might not be the best way to handle it though.
Does the person have the money to pay you back? Is he traveling, eating out, buying new clothes, buying expensive cars? That would annoy me. Since you ask the Q I assume it bothers you a little that the money wasn’t paid back. If he works hard and barely can live check to check I would leave it be.
It would have been better to say something a long time ago. That’s the biggest obstacle I think, the amount of time that has gone by.
You could ask indirectly through someone who knew about the loan. In our situation it was my husband’s mom who asked us to do the loan. Since she brokered the deal, we might have let her know if it wasn’t paid back and let her go to the person to tell him to pay up for the sake of the family. Not sure that is good advice though. Complicated games in the family can be destructive.