Anonymously Helping out a Friend Financially - Good? Bad?

I need to know whether or not this would be weird, or if there are any other options that would be better for me to take without overstepping my place.

I know a couple that I am not super-close with, but with whom I do have a social relationship going back almost a decade. We’ve often carpooled to concerts and whatnot in the past and attend the same events. Last fall they finally tied the knot - and since then she has been laid off and diagnosed with MS, his car died, and his mom got critically ill and is dying. They are really struggling right now, and a mutual friend tells me it’s a lot worse than they are letting on.

The two of them are some of the sweetest people I know and I want to help, but I don’t know how. I think they would see any offer of money as a handout and it would be a little out of place for me to just offer out of the blue. Anyway, I was thinking about maybe sending some giftcards to the grocery store and other necessity stores anonymously to their house. Would this be weird? Are there better ways I could help?

i think it would be perfect. the cards would “just” appear, they wouldn’t know who did it, so they wouldn’t feel “funny”. and you would have a secret warm and fuzzy “done did good”.

i see it as win win.

one of my lottery dreams is just sending money to people with no trace of whence it came, just an envelope with a thousand or two. i think it would be great fun.

We had this happen to us at Christmastime–we have really been struggling. Gift cards showed up in the mail, with a printed-out flyer-looking letter that just said “Merry Christmas Dangermom!” Each card came in its own letter, in case you’re wondering, and were addressed to different people in our house. I can tell you that it was hugely appreciated, as much for the thought as for the money. I filled the kids’ stockings from those cards, and did some other things.

Another way to do it that I have seen is to give the money to a third party–a friend, pastor, or whatever–and let them play Santa. I was once the delivery person that way and it was good too.

You could do cash or cards, but if you want them to be able to pay bills or buy necessities, stick with either cash or really general cards like Safeway or Target. We were given both practical cards and a couple of fun ones, which does give the recipient permission to buy something fun, which they will not otherwise do, but is less practical.

This is awesome. Absolutely a great way to help out without the feeling of shame that many people feel when circumstances change like this. Avoid the mastercard/visa like gift cards that stick on hefty service charges and stick with their local grocery store, gas station and if you would like to add less practical stuff make it either something you know they like or something generic enough that they can find something there they’ll enjoy.

Very sensitive of you to look for a way to deliver it without injuring their pride.

Thanks for the responses! I was debating whether or not I should just send cash if they need it for bills, but I figured the money they saved on not buying food/whatever could go to them. And I guess it’s just been drilled into me a lot to not send cash in the mail, even though I guess cards could be lost just as easily.

Gift cards spend like cash if they are intercepted via the mail; so yeah, you could just roll the dice and send cash instead.

I’ve payed something for someone. By not telling them it’s you they don’t expect you will help in the the future and they don’t feel awkward around you. All the win without any future entanglements.

Can utility bill (or something like that) be easily paid anonymously for someone else?

I had people help me out like that last year and it was fantastic. I recommend cards to places like Wal-Mart or Meijer’s or Target - someplace with both groceries and general goods.

Same here, after our freezer went out. I know it was some people from church, but I don’t know who.

No suggestions, just to say that you’re a good person for doing this.

I send money anonymously all the time to people who need it. I usually spend the extra $$ to send it Priority Mail. It makes me feel more likely that it won’t get lost in the junk mail.

If your mutual friend knows of an organization that’s already helping them, maybe you can funnel it through them (earmarked donation, I know several of my local aid organizations accept them, but not all).

I have different take on this. I think these people need to know who helped them out. If you ever need help they can do the same. That’s how life works. You help someone when they are in need, and they help you.

I don’t think it is necessary to repay the exact person that assisted you, to the point where they “need” to know who helped them. First of all the day when they can reciprocate may not come for a long time, or ever. If it never comes, they may feel badly, or even embarassed around the OP because they are unable to meet a social obligation that. Moreover, if that time when it does arrive, the OP may not need any assistance themselves right then. I like the concept of “pay if forward” – instead of “repaying” the person who assisted you, you help someone else out with no expectation of reciprocation.

When I help someone and they know it’s me, I tell tell them it is not a loan, it’s a gift. I just say that they should help someone else in the future when they are back on their feet.

If they are a friend, of course they’ll help you in the future.

I did 2 different methods: 1. I left cash in drawers so it was like “found money” in every sense of the term. 2. I was house sitting while they were out of state for his mother’s funeral, and paid their bills that month because they couldn’t afford it.

I may be mistaken, but it sounds to me as if you think that people feeling indebted to each other is a good thing; I would never want to feel indebted to someone, I would never want anybody to feel indebted to me, and indeed the people who for example helped me when Mom was bedridden made it very clear that they were not expecting any kind of “payback”.

Some people (you if I’m reading it right) believe in “turnaround”, I believe in “pay it forward”.

Can’t find the quote, but someone said anonymous giving was the very best kind. Certainly do it.

One of my coworkers became ill a couple of years ago over the holidays (colon cancer!).

Our company gives us a $25.00 gift card to the grocery store for a holiday present (too generous, I know…) so most of us donated our card to the coworker. We just collected them from anyone wishing to donate to her and mailed them in an envelope without even a note.

She recovered and still talks about how much she appreciated the cards.