How do I help my neighbor feel more comfortable asking for help?

I used to help out my grandparents and their friends with stuff. My grandparents always insisted on paying me and sometimes their friends would pay me too.

At first, I'd refuse until they told me that it makes them feel bad. So, I'd gladly take their money and save it in an envelope. Then, when something would break or need to be replaced, I'd say, "oh, I have an extra one of those! Gimme a couple of days to look for it." And then I'd buy it with the money they gave me.

My wife and I would also take my grandparents out to dinner using the money they paid me, or I'd buy groceries and cook them a few meals, but tell them that I accidentally made extras.

Unless she's paying you way too much, just take the money and then use it to fund helping her.

Maybe ask her for something small so she feels like she's helping me too?

If they always insist on paying, yeah, that's what I usually do. Typically phrase it something like, "No thanks, I don't really need the money, but I do like [biscuits | cookies | whatever her cooking specialty may be]. Helps if you know they like to cook, though.

Everything's been addressed that I can think to add, but I just wanted to say: y'all have got the right mindset and I appreciate you for it. Keep making the world a little bit better however you can.

Another perspective, from a woman in her 70s. It's lovely that you're being so thoughtful. But this whole thread reminds me of a train journey I made a little while ago. A young man took a seat next to an older woman, maybe in her 60s. For a hundred miles or so he told her loudly about his life - university, sports, ambitions. She got off at her station, "lovely to meet you" etc. He then phoned a friend and told them, "Yes I'm on the train, just been chatting to an old dear, keeping her company..."

All of us "old dears" in the vicinity were smirking and side-eyeing each other, it was hilarious. My point is, are you sure she's decrepit? I'd be a little taken back if someone did chores for me unbidden, however well motivated. And although I live alone, I'm not lonely. I'm not criticising your kind impulses, just warning you against being a touch patronising.

Try and spend time with her just to spend time with her, if she sees you as a friend she might be more open to asking for help.

I have an example and a suggestion.

There's an old lady living across the street from us. We've been living here for twenty years and her partner passed away there about two years ago. I want her to not feel alone and I know she really loves my beef stew (I honestly make a savage beef stew) so when I make some I get one of our kids (who she knows since they were born) to drop some over to her. She always drops back the bowl with like some fruit in it. I considered saying not to but I actually feel like she likes the reciprocity. Anyway if you get a nice smell coming from that lady's place some day, drop that in to the conversation. She'll remember and you'll get some great food then there's balance.

Another way is for it to "just happen" in a silent way. Just say nothing after you've done it and gently refuse payment but put the kindness on her.

"Oh no, I'm happy to do it. You're very kind to offer but I absolutely couldn't. Thank you though. You're very kind."

That way she won't feel indebted.

Thanks for being a good person. It feels good doing something nice for someone, don't deny her that same good feeling. My suggestion is take the money and spend it on rock salt. I try to help people from time to time, my parents are 80. I can't be there for them all the time so my hope is that if I help others maybe fate/god/cthulhu will send someone to help them

No matter what she offers refuse as politely as you can ... if she really insists and is upset about it, accept it and maybe just use it to buy a new shovel or something.

I have elderly neighbours myself and I help them when I can or when they ask for it. Just let them know that you are available ... but also set boundaries and don't let them think that you are on call 24 hours a day. My neighbours asked for a help a month or so ago and I wasn't around to help so I had to tell them I couldn't. But nines of out of ten, I'm there for them if they ask. But at the same time, if they called me at 2am for an emergency, I'd run out to help them.

Just remember the golden rule about neighbours and being neighbourly .... 'stay close to your neighbours but not too close' .. be nice to them, but don't involve yourself too much or too far as that will get you into deep trouble that might not be good for either of you.

Ask her to pay you by sharing a meal, which is actually another kindness to her.

Just be clear you are an option for help if needed, other than that be nice and don't over worry. People with limited mobility like to run their own lives, just the same as we all do. It sounds like you've been a pleasant neighbor, keep it up and continue shoveling if you want. Snow is usually considered fair game for anyone willing, and people almost always appreciate its removal. If you don't want pay, say it's not something you accept for snow removal. Pretty normal for people who grew up in snowy cities to volunteer some shoveling time. If they ask you to stop, you should heed their request.

The other advice is solid, and I agree with it all as of this posting. I did want to focus on the money thing.

I think you should accept the money. Some people, particularly older generations, view money as sign of respect, and turning down is against their understanding of social protocol.

You could even use it to get her a nice gift (flowers, cards, gift basket, etc).

Do you have an interest in the time of her childhood? Perhaps learning about her experience of how the world has changed? Most people find thinking and talking about the world they remember to be enjoyable and she may have interesting and unique perspectives on things. This can lead to learning about bigotry though, so be cautious, but learning about how the world has changed from her perspective could be very interesting.

The 1960s were a time of massive cultural change and technological advancement, and the 70s were also really cool from a change perspective. Learning how she did things like washing clothes, buying food, learning about something she was interested in, and so on can be really fun.

Once you have spent a little time chatting and maybe having a tea or coffee it can be a regular little social thing you do, and doing the snow shoveling is much easier to accept from someone you know than from a stranger. It would also make it feel safer knowing who you are rather than just some random younger guy.

Buy her some Bengay and prunes.