> The goal is to never be asked for money again and slowly bled out by frequent sob stories. If they know they are already into me for more than they thought they would get, they won’t come back, and I don’t look like a jerk.

This only works if the people have fucking shame.

I have a relative who has no shame and will keep taking as much money as you'll let him take.

So I limit what i give.

He keeps saying to me it's ok if I borrow and charge him points ... but in the Christian tradition usury is a sin so I don't and though I'm not a religious person, I was raised with mainly Christians principles that I adhere to because they just seem like good principles in general to live by.

Plus I'm pretty sure if I did charge interest I'd just be disappointed when he doesn't follow through with interest payments knowing how flaky he is with his money.

I'd rather just give money and give what's comfortable.