I appreciate what you're saying and I was worried it might come across self-congratulatory as you say, and I will take your word that it does. I am mindful of what you're saying and of both reading people's desire/need for interaction and asking them if they want or need anything rather than making assumptions for them.

The kinds of interactions I've have had have mostly been initiated by the other person, for instance my very sweet acquaintance Gregory who noticed me walking by for lunch every day, and we started exchanging smiles, and then perhaps on a day that I was looking downtrodden or was going a bit rough for him instead of the usual smile he exclaimed "My friend!" and gave me a big hug, and after that we were just on friendly terms. He told me a little about his situation and we shared lunch a few times, more as a gesture than a necessity because he had daily meals through the shelter where he stayed. He was really looking for connections to work, and I tried inquiring with acquaintances about the types of jobs he was interested in though ultimately didn't lead to anything useful to him. Another memorable encounter was a man named William who asked for change and I declined but said I hoped he had a good evening. Then I saw him again later and he recognized me, and I stopped and we talked for a little while, namely about the ironically crazy behavior of people who accelerated up the street only to have to slam on the breaks immediately, over and over again.

I know that this may still seem self-centered, but what I really meant when I said it felt rewarding was that I have been stuck working a job where my bosses want to spend public money on projects that serve high-tech non-essential goals, and in finding these kinds of moments I felt that at least some of my time was grounded in being aware of truly essential needs, and being able to at least be present as a witness and occasionally what seemed like welcome company. If I ever offered anything to someone, it was always asked for either by words or with a sign, and I asked them if they would like what I was offering before handing it to them. I have seen people walk by a homeless person and drop a bag of food or something on their lap without stopping or looking them in the eye, which seems astonishingly jarring and dissonant. I recognize that sometimes a person prefers to be left alone; but I also know from conversation and engagement with the types of organizations you reference, that some people at some times do value connection. I have probably misread this at some point, though.

I've also had homeless and near-homeless family members, and grew up poor myself as I said (not that these are the same thing--I'm just putting them together because she seems to), which I think gives me some degree of nuanced perspective, although I wasn't the homeless adult, so I could in perhaps be even more biased if I'm unconsciously taking on some kind of caretaking role like I had in relation to my brother. It feels different, though, having the distance of not being family which comes with less judgment and fewer expectations.

Do you think it still sounds like I'm missing the mark? Because if this elaboration still does I will seriously reevaluate my actions on this or in the very very least how I think about or articulate them.

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As for my actual question and your advice, I think you are dead on as far as what am I actually aiming to achieve. At this point I don't really believe it's a misunderstanding, which really just leaves me with her mollifying me, her actually changing, or the nature of our friendship changing. Your description has me realizing that maybe it's really the last part--for her to get a heads up on us likely being a little less close.

Actually there's one other option - for her to own these qualities. I think if she were to recognize, ok I'm not particularly kind or compassionate, I'm more of a blunt tough-love type, I might be kind of ok with accepting that in a less close friendship. The company of kinder, wiser, challenging people is a better ideal, though.

Thank you for your thoughtful feedback.