How to Anonymously Send Grandmother Money?

Could you maybe talk to her complex and see if they'd tell her she qualified for a discount... But really, you're paying $200 (or whatever amount) a month of rent?

Please don't let her think she's forgotten something important that she invested in. Memory is an important and potentially scary thing for elderly folk. Get her gift cards to her local chemist or take her out/visit regularly. Unless she's under enormous financial strain, receiving your money is going to cause her stress. Unless you are upfront. What about paying her phone (net- ? Skype) bill and calling her a lot? Tell her it's her gift to you, access to your beloved grandma.

This is possibly the most heart-warming dilemma I've seen here on AskMe. What a lovely pickle to find oneself in. I would just tell her what you wrote here: how much you love and appreciate her and that nothing would make you happier than the ability to pay for her to have some luxury in her life. I think if you frame it like you're lucky enough to be financially blessed, you have all you want and you would have genuine joy if you could share this with her (money for beautiful books, expensive yarns, day trips, restaurants, shows...all the fine things in life that money requires), she would be hard pressed to say no to your generous offer. What seems critical is to frame the gift in terms of treats; of luxuries she deserves in her life and that it really isn't a present from you; she'd be giving you a present by allowing you to pamper her.

I know all about proud family elders. Everytime you visit, leave some money in a card somewhere she will find it after you've left. Just say something simple in the card like, "for being the best grandmother ever, love xxx". Don't ever mention it, and hopefully she won't too. If she does, just stop her anxiety by saying, "grandmother, it's a gift. Please accept my gifts given with love!"

I had similar problems over giving to my own grandmother. What worked for me was offering to pay for services I - ever - used, and buying groceries. If you talk to her on the phone, offer to pay the phone bill. If you visit her and use so much as more lights, offer to pay electricity. Does she live somewhere FreshDirect delivers, or some similar service? Tell her that it makes you feel guilty that you don't live close enough to drop off groceries, /like a grandchild should/, and so you've found this cool thing that lets you do your family duty! Basically, if you frame it as something which will make you sad if you can't do it, she may be more willing to give.

Maybe you could tell her that you are getting a great deal, a discount really! if you add her to your cell phone service? Then you could get her a nice new phone, pay the bill each month and no one would be the wiser.

Can you make up some song and dance story about dividends from an investment she must have accidentally made some time ago? You remember, Grandma, when you sold that house they put part of the proceeds into shares that are now paying out $200 a month as an annuity? Do you want me to send you that in cashiers checks or gift cards?

Perhaps you could think about what she might spend the extra money on and have that delivered to her? You could have, say, fresh flowers delivered on a regular basis, or a grocery hamper with some of her favourite treats, or some pre-prepared gourmet dinners. Subscribing her to a something-of-the-month club could be another option. By using delivery services, you add a layer of abstraction between you and her that will make it harder to trace back. (Though I suspect she may suspect you anyway!) Whatever you decide, it's a lovely gesture.

You can likely arrange with her medical providers to pay down some of those bills anonymously, if you can find out who the providers are. If she asks them how her balance went down, they can tell her that they're not at liberty to say. This seems to happen a lot in the medical administrative world, that things are just not explained to people. This is wonderful of you to do.