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It’s very awkward & I would avoid it if possible.
Source: I’ve loaned my mother & a friend money.
Avoid if possible but if not consider it a gift
You could ask them to agree to sign some type of payment agreement, if that is the route you want to take, definitely make sure that you get it notarized!
However, I have always been advised to never loan more than you would be comfortable with not getting paid back. This way if they do pay you back, Great!! However, if they don’t, then you are not putting yourself in a financial hardship either…