Decide Whether to Loan a Large Sum of Money to a Family Member

They have asked for help and you can probably find the money, but lending to family rarely stays simple. This weighs what you can genuinely afford to lose, whether a gift protects the relationship better than a loan, and what a fair written arrangement looks like, then gives you a straight answer either way.

Help me decide whether to loan {AMOUNT} to [family member] who has asked for help with [the reason they gave]. Weigh up what I can actually afford to lose, whether a loan or a gift changes the relationship less if it goes wrong, and what a fair, written repayment arrangement would look like. Give me a straight recommendation, not just a list of pros and cons, and one sentence on how to say no if that is the right answer.