I'm extremely passionate about the homeless, and get more joy from helping people on the streets than from just about anything else in life;
I do have obvious reservations about money, so what I'll typically do is, whenever I see someone who is undoubtedly living out of their backpack-is just go up to them and ask if, since I'm going there anyway (even if I wasn't) I can possibly pick up an extra lunch for them at any nearby drive thru chain..... or if they are sitting in front of a gas station, I'll say something like "hey, if you need anything at all, feel free to come inside with me and just grab anything you want and I'll take care of it. It's my pleasure-and hey, what's your name by the way?"
I know this part will sound a bit weird and perhaps purposefully juxtaposed but it's just a fact. Very often I wind up telling bold faced lies in order to get people to even accept help. Everyone has an ego and nobody wants to feel like they need a handout. It's pride that gets in the way, and when I encounter prideful resistance (which is often) I'll just merrily joke about how I am terminally ill and just trying to do as many nice things as I can before I kick it because I've really fucked up a lot of shit in the past (that part is true) and then usually I get compliance without further issue
I find many homeless people utterly fascinating. Anyway, I just go ahead and let them pick out whatever they want-food, beverages, etc (except alcohol) and then I do not tell anybody about what I do because I feel that somehow cheapens the act of doing good for others. But that's just me. The few times I have gone bragging about my selflessness to friends..... I felt a bit pathetic afterwards.
Don't get me wrong: I encourage others to do good every chance they get. Even if it's just to get a tax write-off, to look good in the presence of others, or feel important due to the implied characteristics of being an altruistic person... Yeah, I don't think it matter really. The ends justify the means here in my book since I secretly think that (myself included) a lot of people who do good deeds.....do them because most of their time is spent doing things that certainly aren't worth bragging about, much less be proud of