Back in the good old days, at least according to many movies and my study of American culture, seeking to borrow money from a friend was considered a sure-fire way to lose a friendship. Accepting charity from a friend was a bit different: part of friendship is offering assistance (“A friend in need is a friend indeed!”). I have, however, often, but not always, rejected kind and good faith offers in that category, mostly when the charity came in the form of in-kind benefits.

But now I am beset with this question: How should I handle a friend—not close, but genuine–who has asked me for money,not a loan but a gift, in a personal crisis?

These are the relevant facts:

• I have known him for over 40 years, in the course of my many theater exploits.
• He is near retirement age, but still working.
• He recently had a bout with cancer and is still in treatment.
• He lost his job, and with it his health benefits.
• He just sent me a recitation of his problems and asked via Facebook message if I would help him out financially.
• He is a good human being, based on what I know about him and what I have observed.

If Grace were still alive, I guarantee that she would have vetoed any suggestion that I accede to his request. As for me, I am always inclined to help out in these situations even when I shouldn’t, and without going into embarrassing detail regarding all the metaphorical financial swords of Damocles dangling over my own head right now, this is one of the times when I really shouldn’t. I recently took out a personal loan myself to get through a cash flow crunch.

And yet…my friend really must be desperate to ask me for money: unless he has been cancelled for some hideous conduct I am unaware of. I assume that I don’t rank among his top 50 friends and family members, and he wouldn’t make my Top 100. Is he asking for a token amount? I have had bad experiences with that. I wrote a post a while back about cutting off a friend, a closer one than this one, who had been only contacting me to ask for money for years. Grace had once “loaned” him $10,000 (that we couldn’t afford), and it was like being extorted thereafter. Not only didn’t that now-deceased friend indicate any intent to pay back what we had already given him, he kept asking for more.

My question is: Now what? How would you handle this situation, or better yet, how have you handled it, and were you satisfied with the results?