I think first and foremost, good to sit down and discuss it with this family member. Basically, it is to have a common understanding that this is your money that you're talking about, and the gravity of returning the sum. If he/she understands it, over time there may be lapses. So if you decide to lend money to the person, be prepared that you may not get back whatever is lent, should you decide to preserve this family relationship. However, if you feel this person's character is questionable (i.e. does not respect the relationship) but still want to ensure you get back your money after lending, I'd suggest to get free legal advice and maybe see if it's reasonable to draft a legal document to enforce repayments, as well as understand what will happen in terms of cost and proceedings, if this borrower doesn't repay. The person may think twice of borrowing from you, if he/she needs to sign a legal document, because the issue now has more weight to it and it is a legal one at that. If he/she decides to proceed, it will give you a piece of mind. https://www.lawsocprobono.org/pages/community-legal-clinic.aspx Do not let anyone treat you in a way you do not want to be treated, not even family.