It's tricky. I've both personally visited homeless shelters where ex-homeless people lived and worked under guidance and coaching, and the general story from them was 'don't give money'. Maybe of them used drugs in the past and said the cliche is completely true.
In that case, if someone asks, best politely say no, direct them to places where they can get help (most advanced economies have some capacity in every city), and take the money and donate it to said places or another cause when you get home, pool it in a jar for a once a month or whatever donation if you want.
On the other hand, someone close to me in my own family was homeless for quite some time after a wrongful prison conviction. Despite him having enjoyed a great life, big social circle, never addicted, enjoyed higher education and a nice career etc, typical upper-middle class stuff, he struggled on the streets. His prison time carried stigma that he didn't deserve, but couldn't be proven innocent. He stayed on the streets partly because he was afraid to ask for help, to be seen. And partly because he was convicted on a holiday, outside of the country he knew well with a limited network.
Someone else in my family took him in, from the streets, gave him some money, a roof to stay under etc. And that's why this person is part of my family now. And I've spoken to numerous ex-homeless who had no addiction, and just didn't have any food or a roof to stay under. Or recently when we partially funded the first month rent for an illegal immigrant. He now has a painting job etc. It's an uncertain existence for him, but he's got an alright life and contributes his share to society and is financially independent. The issue is that cases like this require time to evaluate that you tend not to have passing someone by.
In short, I'm similarly conflicted and usually do give. When I have time I tend to have a chat and ask what they need. They'll say 'some change' or whatever and I'll just cheerfully say huh, why? And they'll say for some food or w/e, and I'll just hang out with them for 20min and buy them some food and eat with them. Best case he actually wanted money for food and had some social contact, worst case I fed someone who didn't starve and had a nice chat.
In that case, if someone asks, best politely say no, direct them to places where they can get help (most advanced economies have some capacity in every city), and take the money and donate it to said places or another cause when you get home, pool it in a jar for a once a month or whatever donation if you want.
On the other hand, someone close to me in my own family was homeless for quite some time after a wrongful prison conviction. Despite him having enjoyed a great life, big social circle, never addicted, enjoyed higher education and a nice career etc, typical upper-middle class stuff, he struggled on the streets. His prison time carried stigma that he didn't deserve, but couldn't be proven innocent. He stayed on the streets partly because he was afraid to ask for help, to be seen. And partly because he was convicted on a holiday, outside of the country he knew well with a limited network.
Someone else in my family took him in, from the streets, gave him some money, a roof to stay under etc. And that's why this person is part of my family now. And I've spoken to numerous ex-homeless who had no addiction, and just didn't have any food or a roof to stay under. Or recently when we partially funded the first month rent for an illegal immigrant. He now has a painting job etc. It's an uncertain existence for him, but he's got an alright life and contributes his share to society and is financially independent. The issue is that cases like this require time to evaluate that you tend not to have passing someone by.
In short, I'm similarly conflicted and usually do give. When I have time I tend to have a chat and ask what they need. They'll say 'some change' or whatever and I'll just cheerfully say huh, why? And they'll say for some food or w/e, and I'll just hang out with them for 20min and buy them some food and eat with them. Best case he actually wanted money for food and had some social contact, worst case I fed someone who didn't starve and had a nice chat.