As I understand your question, basically you want to know how you can stop offending people in some way, when your intentions are good.
I’m in the same boat, often it seems, both here and in person, so it’s the same lesson I’ve taken a long time to learn. I’ll pass along the advice people have given me that helps.
1) There is such a thing as “too much truth”. Decide if a fact (or opinion) is actually what the person wants, which is entirely different than what they “need”. No matter how carefully and caring you deliver something, if the person doesn’t want to hear it, 95% of the time it’s better to keep it unsaid.
2) Distinguish between complaints made to vent or entertain and complaints made as a request for help. It’s not always black and white, but people complain a lot. Most of the time it’s something to fill dead space or to vent. As an example that always gets me into trouble, people complain about their jobs constantly, and my first instinct is always to try and help them find a better fit. If they’re actually looking for a fix, this can be one of the kindest things you can do, but people rarely want to change something that large.
3) Start with “can I help?”. Ask if it’s ok before offering anything further. I try to help people who have something that’s obviously heavy or awkward for them to carry. Whether it’s groceries for older shoppers, a carseat to someone with a toddler as well, or lumber at the hardware store. I had to learn to ask, how to ask, and when even just asking is probably going to stress people out.
In a world where holding the door for someone or asking how they’re doing can be offensive, you’re simply not going to get through life without offending someone, no matter how good your intentions. You have to find a balance you can feel good about and that reflects your values with the understanding that some people have a different opinion, and you need to let that govern their life, but not yours.
Sometimes I wish I was wise and controlled like @thorninmud, other times I think I’ve backed off too far and given up opportunities to help.
(danger: unrequested opinion ahead) I think the key is just don’t give up, keep trying to help, but learn to recognize the difference between opportunities to make a difference and times that are likely to offend. In my opinion (again) it generally comes down more to the person you’re interacting with than what’s actually said or done.
Please don’t beat yourself up.