💸 Regret not learning to say no when relatives ask to borrow money

Over the past six years I have lent money to relatives on four separate occasions, ranging from a smaller amount to help a cousin cover a hospital deposit to a much larger sum that an uncle needed for a business he was starting. In every single case, I said yes almost immediately, partly because saying no to family has always felt like something I was not raised to do comfortably, and partly because each situation genuinely did sound urgent at the time it was asked. Out of those four loans, only one has actually been repaid in full, and that too after I had to bring it up twice myself rather than it happening on its own. The others have turned into this strange unspoken arrangement where nobody mentions the money directly anymore, but I notice it quietly shaping how I interact with those specific relatives now, a small awkwardness sitting underneath otherwise normal conversations at family events. What bothers me most is not really the money itself, though the total adds up to more than I am comfortable admitting even to myself. It is realizing that I never once asked a single clarifying question before agreeing, no repayment timeline, no real understanding of why previous loans from other people had not covered whatever the situation was. I just said yes and transferred the amount within the same day every single time. My wife has gently pointed out a few times that I seem to say yes automatically to anyone in the family who frames a request as urgent, and looking back honestly, she is right. I do not know how to actually change this pattern without feeling like I am rejecting family itself rather than just setting a reasonable boundary around lending money specifically. Has anyone else gone through something similar, and did you actually find a way to say no, or at least ask more questions first, without it turning into a bigger issue with the relative asking?

Went through a version of this with my own brother in law, three separate loans over two years, none of them ever fully repaid, and the one thing that finally changed it for me was starting to ask a single question before saying yes, when exactly can you pay this back. Half the requests quietly stopped coming once that question became routine, which told me something about how urgent they really were.