So, to get this out of the way, I'm a cisgender white man from a well-off family in a fairly affluent town. I'm making this post because I want to hear perspectives from those who are different from and likely significantly more knowledgeable than me. (Literally as I was writing this post, I came to the epiphany that I should probably more properly educate myself on socialism.)

TL;DR: What is your opinion on giving money to houseless people you see IRL?

I like to consider myself socialist/progressive in thought---in favor of wealth redistribution via various methods, live and let live, freedom for everyone as long as you're not materially harming anyone, etc.---but I grew up in a fairly conservative household (more socially than fiscally, but even then). Being in a rich area, I never really saw houseless people around unless I went to one of the nearby cities, and the general policy was keep walking and don't look. My parents definitely raised me to be kind and generous, but more in a detached "give to charity" way.

Rather recently, I've really embraced this idea of being socialist, and I've become very free with giving my money in particular (though I'm aware I could do more, like join a DSA branch or somethin'). I love giving to non-profit organizations when I can, I support creators I like on Patreon. I've even started giving to people on Fedi who I've seen need money for whatever reason. Spread the wealth, right?

Now, things have changed where I live, and even in my rich lil burb, you can usually find at least one refugee or houseless person when you go out to a grocery store or something. I just saw a guy who was standing outside a grocery store asking for spare change, and it was a rare occasion that I actually had cash in my wallet. On my way out, I gave it to him. Simple.

But I feel weird about it. I have all these ideas in my head from White America saying that they'll just buy alcohol or drugs with it or that they're scamming me or anything else like that. Then on the other hand, I think that it's just as likely (if not more) that they're going to spend it on things they actually need to live and how it's not my job to police how they use their money. And then on the third hand, I think that maybe it would be better to donate money to organizations that help out houseless people than just giving money to random people. Then on the fourth hand---you get the idea.

For those of you who actually read the whole post and didn't stop at the TL;DR, I have a few questions:

1. Why in God's name did you actually read this whole thing?
2. Are these feelings normal or am I just a self-centered prick?
3. What are your opinions on giving money to houseless people you just randomly meet?
4. As a bonus question for the socialists out there: Any recs on socialism learning resources for someone who likes reading, but doesn't like reading books?

For those of you who made it all the way to the end, thank you for reading my neurotic ramblings.

EDIT: I didn't really expect this to blow up... but thank you all so much for your perspectives on everything. It was exactly what I was hoping for and exactly what I didn't think I was going to get. I tried to read everything and I feel simultaneously less conflicted, but definitely more... not confused, but maybe full of ideas?