Generous gesture or patronising?? Trying to help a friend

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This is more of a WWYD scenario. I have a friend who is a single / lone mother to DD age 14, no father since before birth. She is in an awful situation financially after becoming ill and has been trying to work against medical advice. She has finally accepted she can't do this and is now working a few hours a week more for MH than anything. I presume she is getting some sort of disability payment. She has always struggled financially but is extremely proud and will never accept "charity". In the past I found it a bit frustrating as I might buy her an expensive coffee but she would insist on paying me back the next time, then sit there with water cos she couldn't afford two. These days if we meet its for a walk or we buy our own drink etc.

We talked frankly recently and i realised her situation is worse than I realised. She does not have enough for food sometimes and is worried about her DD's constant need to eat. She mentioned a situation where she ordered an item for the house that was £6 more than advertised and how she had no choice but to pay, so an item her DD needed for school had to be delayed by another month. She was nearly in tears telling me about this £6 deficit.

I was thinking of buying her a voucher for her local supermarket for a few 100s but don't want her to be upset or feel indebted to me. I am not sure if I should give this to her or drop it in anonymously. Would that be a really strange thing to do? I think she may have gotten over her attitude against taking hand outs as she mentioned how generous some neighbours were for buying her groceries when she was recovering post surgery.

For context her prognosis is horrific - she is terminal and will decline slowly becoming disabled for a time. Her hope is that DD won't be a carer and that she will hold off the disease til DD is finished school then make a swift exit. Thats her best scenario. She is in relatively good health now and is saying she would like to make the most of her time, but her lifestyle right now is miserable.

That’s sounds so tough for her, and you sound like a lovely friend.
Given that’s she has insisted on paying coffee back before now, I would pop it through the door anonymously.

Personally, I would find a gift card of a "few hundred" to be very patronising, and I wouldn't like it. Even though that would be a ridiculous attitude to a very generous and kind hearted gesture! So, I would probably offer £50 and, if accepted, another £50 in a few weeks.
In the interim, I would make sure she is aware of any entitlement to use food banks if she would be willing to do so and, maybe, invite her (and her daughter?) to lunch/dinner at yours, and send her home with any leftovers. She might find that more acceptable.

I think you should do whatever you can to help her out. I don’t have a firm belief about what that should be but her situation is dire and she is your friend so it would be good if you can figure out some way to be a supportive friend qua friend and also ease some of her burden as a struggling single mother.

I think what I mean about the first issue is trying to find an acceptable way to host or treat her for the “friend” moments so that she can accept a treat (like a coffee) without having to suffer or debit herself to “repay” it. Maybe that is shifting to activities like hosting in your home or offering to take her to the theater “because i have two tickets” where there isn’t a clear monetary label Or an obvious cost to you to be repaid.

On a deeper level, and I don’t know if this is something either of you would want, I wonder if you could make things a bit easier for her now by addressing what must be her long term terror for her daughter. I am thinking of whether you could/would offer to stand in loco parentis or at least as a wise aunt figure for her daughter in the future.

Obviously the money issue seems mist pressing but, at the same time, if my prognosis was terminal and I had a young daughter I would be most concerned that she have some kind of future family-like support as I decline and after I’m gone.

I have a friend I worry about, similarly. I wouldn't do the anonymous monies/vouchers because she'd worry very much about where they came from and what it all 'means'. And then I'd either have to fess up or fib. Not good.

This is a lovely gesture and you are an amazing friend.
Could you buy the groceries and take them to her pretending that you won/were given vouchers and thought to share your good fortune?

I think perhaps that is too much and she would be embarrassed.

Would she accept a smaller amount occasionally or a small bag of groceries?

Making extra when you are cooking or doing some batch cooking just for them and regularly popping round with some meals they can stick in the freezer and reheat, perhaps with the odd treat thrown in, might feel less full on to them. A couple of hundred in vouchers could feel a bit much.

I think there has to be a conversation about how her pride is disadvantaging her daughter. It has to be really carefully done, and with huge empathy. But I think that the only thing you can say is that you're in a position to help, that you want to and that you've held off offering because you recognise and understand her pride. BUT that you've seen how her DD is being disadvantaged by the situation so no longer feel that you can just stand by without making the offer that you want to.

I wish you luck. It will be difficult. But I think a voucher out of the blue would be too much, and yes, absolutely don't do it anonymously.

That sounds like a really difficult situation for your friend and her daughter.

I think you are right who are trying to help her. You are very kind.

It's hard to tell how she will react if you give her the voucher - sending it to her anonymously could be an idea, but it might creep her out? Might feel weird to receive something and not know who it is from.
I would send it to her, and write that it's from you, and perhaps not mention it afterwards.

I’d sit down and have an honest discussion with her and let her know that you’d be more than happy to help her out in her time of need. Either with groceries or cash or whatever you could.

I know if I had a friend similarly situated I’d do whatever I could.

Pressed too soon

Hardy very patronising

Do it, and hopefully your friend will accept in the kind spirit it is intended OP.

You sound like a lovely friend OP. I feel for your friend. When i was a lone parent things were harder for me financially. Like your friend I was proud but my best friend used to do things like buy my daughter trainers for birthdays or Christmas because she knew she needed shoes or clothes and my god it used to help me out. She used to also just show up with things like bread or milk if she was popping in small things that really meant a lot.
My situation wasn’t as dire as I was able to work full time and my bills were paid so it was more things that daughter needed additionally I used to struggle with.

I think if you are maybe persistent she’ll be more accepting of help and know you don’t wish for anything in return.
Wishing you and your friend the best x

In this instance I’d forge a pretend letter about her winning 2nd prize in an postcode competition and put the voucher in the envelope!

Or you could say you won a bit of money and as it’s Christmas you are sharing the whole amount between family and friend?

You sound like a lovely friend OP. As your friend has a terminal prognosis she will be eligible for PIP and if it's a cancer diagnosis then Macmillan cancer services provide financial support and advice. She will need all of this going forward and to plan for her daughter.

At the end of the day, you know your friend.

If you are close enough that you are prepared to help out to the tune of a couple of hundred pounds, you should be close enough to have on open and honest chat about it.

Let her know that you want to help and find out what she would be comfortable accepting, in terms of both emotional, physical and financial support.

Thanks all for the posts so far, I'm heading out soon so will read in more detail tomorrow.

@pikkumyy77 to clarify, my friend has family local enough and her brother will take guardianship of DD, even if over 18 and until her education is finished. My friend owns her house so ironically DD will be ok when she dies as life insurance will clear the mortgage and the house will be put up for rent, so DD will have a rental income for as long as she likes, or she can move home and live rent / mortgage free forever.

You sound like a lovely friend and your friends situation sounds very difficult.

I would have an honest conversation with her that you understand she’s very proud but you love her & her daughter and don’t want to see them struggling when you can help.

Instead of a voucher could you pay for a regular shopping delivery for them? Put her daughter at the centre of your offer, I hope she will let you help.

You sound like a lovely friend.

I went to a charity auction ball a few months ago and won a £200 Sainsbury’s voucher. I wonder if you could pretend the same and gift it to her?

Is there a way you can speak frankly with her and say you’d like to give something to/help her daughter? (Not her). I get the pride but her daughter shouldn’t have to suffer.

Why does she need to know it’s you. Do it anonymously.

I have found it is usually useful to have an honest and frank conversation. Explain that you want to help and you’re able to. I’d also ask what she would do in your position and make her answer. If she says she’d give you the money then ask her to accept it off you and tell her you know she’d do it for you. If she says she wouldn’t give you anything then I think you have to accept those are her values rather than just pride.

I think anonymously could be very shameful for her. She would worry that everyone considers her poor or a charity case.

i also think you run the risk that she thinks it’s a scam and throws any voucher away.

Could you look at the Olio app and see if there is much activity in your area? It's aim is to prevent waste, not to tackle poverty. You could hopefully collect food (and other items) for you both. It's not a reliable source in many area but might help.