It’s complicated! I don’t think there is a simple answer for this. It depends on the situation, both yours and theirs and the whole feeling of the interaction.

A lot of people get into a desperate mindset and start doing things that don’t help them long term, like seeing that kind of behavior as a sustainable way to survive. I would never mind helping someone in a pinch or giving something away to someone if the benefit to them is exponentially bigger than the benefit to me. But I always look for ways to empower people instead.

I’d rather talk and share ideas with a homeless person and maybe even help them find a free or cheap way to live more comfortably than to just give them money out of my pocket. I’d rather eat dinner with them then throw money. If they don’t want that kind of help then it probably wasn’t meant to be, find someone richer and with more pity. We used to give the homeless people seeds and teach them how to grow vegetables in hidden areas of the city like highway forrest areas. We also would go dumpster diving together and make fun parties and help them redecorate their living spaces to be more bright and comfortable.

It depends on the place too. Some cities it’s really easy to find free food. But I think lifting their spirits is waaaayyy more valuable than money because it will help them find better methods of survival. You do have to make boundaries and be safe though, otherwise you might end up in uncomfortable situations.