If you had a close friend who was in desperate need of cash and you were willing to lend, nay give them money because you had it to spare and it would please you to be helping a friend (and to be putting to better use money that would otherwise be wasted on frivolous purchases) how would you go about making them not feel guilty about it?
Perhaps some more socially able Doper will come and give you advice for something you can say or do, but when I had a friend who was obviously in need of a bit of extra cash to tide them through a hard time I thought that anything I gave they would refuse or insist on paying back. So I put $800 (what I money I could spare) in a blank envelope and stuck it in their mailbox in the dead of night. I still don’t think they are sure who it was.
If you don’t want to do it anonymously, I can’t think of anything more helpful than simply making a firm statement of your friendship and making it clear it is a gift you want to give, that it makes you happy to give, and not a favor, loan or payment. It is not something they ever need to anything in return for - apart from maybe spending it wisely.
Hopefully someone else will be more helpful for you than I have been.
PS: You’re a good guy. Everybody needs friends like you.
Buckler of Swashing Your advice is better than you give it credit for. If I could only get this person’s address I would seriously consider your first idea. I cannot say much more using this medium about the method I have chosen to help than that I hope the friend in question puts the help to the correct use and that I have made that person happier by helping.
I have given money to friends and relatives to help them out and, realising that often attempts to repay debts simply perpetuate the problems, have told them to pass the favour on however/whenever they can do something for someone else. I think that being matter of fact about the gift and trusting that they will “pay it back” somehow, is enough to make people at ease with the idea. They seem to feel less like charity cases and most have later told me how they “paid me back”.
My family’s wisdom is this:
Loan only what you can afford right now. Explain that as far as you are concerned, the money is a gift, and you don’t expect it to be repayed. Explain also that you will never give the person another such loan unless this one is repayed.
Seconded. “Look, I’m the last person you need to pay back. When you have some extra cash, set it aside - but don’t worry about me until you get everything else taken care of - use it as your emergency fund. When you really have extra, you can pay me back then, or you can use it to help someone else or give it to charity.”
I’ve done it as a “pay it forward” sort of thing. I’ve given them the money, no strings attached, and told them that when they got flush again, they should do the same thing for someone else. It wasn’t a handout, it was a hand up. Somebody did it for me and my giving them the money was my “paying it forward”.
Do you know what they need it for?
If it’s for something like utility, phone, house or car payment. You could pay the damn bill yourself! That way they have no choice in the matter…
Or just deposit the money in their bank account if you know what bank they use.
Now that’s what I call sneaky in a good kind of way. 
I was in a desperate spot earlier this year. A friend lent me money, and I felt really bad about it. But, I was really in no position to say no. I don’t know if there’s any way to make someone feel great about it; if they need it they’re probably feeling pretty bad about themselves as it is. But, I assure you, that it will mean the world to them.
I’d just make very clear that I won’t miss the money and there’s no need to worry about paying it back, and (since the person will likely insist about paying it back anyway) that I’m confident he’ll do so when he’ll have settled whatever problem he might have, and not to worry about it nor even think about it till then, even if it happens to take years.
I’d do the “pass it forwards” thing with people I don’t really know well and I’m not necessarily going to see/hear about again in the long term.
I too am of the school : “loan only what you can afford to give, and assume from the start you won’t ever get it back”.
I’ve been on both the receiving and giving end of these transactions.
Receiving–it was most helpful to have the money as a gift, not a loan. I did not need any more guilt or pressure, I needed food, gas and hope.
Giving–I share the circumstances in which I needed to receive, how I felt, how I got over it. I stress that I know how difficult it is to accept help–it is very humbling, etc. I ask only that when the recipient’s life turns around, they help someone else. I’ve been told later that the confidence I expressed that “their life would turn around and they’d be able to help someone else” meant as much as the money. A “wow, someone believes in me, I must be ok” kind of thing.
Anonymous is also good–although I’d use a bank check or money order not cash. And I’d include a note, since the encouraging words can be healing.
The kindness of a friend who helped me out with a GIFT of money saved my neck once. My friend expressly told me it was a GIFT and not a LOAN.
“Besides,” he said, “you’d do the same thing for me.”
A few years later, GrizzWife and I kind of “adopted” a young couple living in the wilds of suburban Washington DC. Sweetest kids you’d ever want to meet. One day, his tools were stolen from his truck (he did construction work). We gave them a few hundred bucks when we found out about their plight. I remember saying something about how we’re sure that they’ll run across someone in their future who, due to circumstances out of their control, find themselves needing a helping hand.
Help out your pal. If you can, make it a gift; not a loan.
Let them know that you’re sure that they’ll do the same thing for someone else in the future.
“Hey, I’d just blow the money on booze and hookers anyway; might as well give it to you.”
Depending on the friend’s personality, you could joke about it. I loaned a substantial amount of $$ to a friend once. I joked about it, threatening to pimp her out to make it pay her it back She thought it was hilarious, because she knew there wasn’t a remote chance in hell of that happening. So, YMMV.
Give them the money in their hand - in an envelope perhaps- and tell them they can give it back to you right now, or at some later point, or not at all, their choice.
bolding mine
Umm, don’t mean to sound uncaring or anything, but how good a friend in this is you don’t even know where they live, or can’t find out?
It’s a work friend. Most of my work friend’s addresses are unknown to me and I’ve known them for up to four years. The person in question I’ve only known for about half a year. At the moment, to keep this thread still fairly hypothetical, I won’t say more than that.
I once loaned my pickup truck to a couple we knew and loved, so they could move. They had a little fender-bender (about $200) with the truck. They were broke, and I knew it. I got the bodywork done. The next time I saw them, they asked how much they owed me. I said, “I have some good news, but it’s going to piss you off. I’m not going to let you pay me for the crash, because you can’t afford it.” I also said nobody would ever again borrow my truck unless I was driving.
I was right. They were steamed. I’m still convinced I did the right thing.