Reminds me of a time a few years ago when I came into a large sum of money. My actively JW brother found out about it and sent me a seriously groveling email hoping I'd lend him some money to buy a car he needed (and he really did need it). I told him I'd just outright GIVE him the money, no strings attached. We had to meet covertly in a hidden corner of the public library so that nobody would see him receiving the check from me. It was ridiculous!
(He returned the favor a couple years later though: When my hubby's car died, my brother -- using that car I bought him - drove us both back and forth to our jobs for a couple weeks til we got another car)