I keep some cash in my pocket specifically in case I run across someone asking for money.

And then I live like a hermit, almost never going anywhere, so it's rare that I actually have occasion to give in that way, but you know.

Also, in my experience, it's not necessarily homeless people who need the money. I've seen people (claiming they're) close to losing their housing who are hoping to raise enough money panhandling to make their rent this month.

Of course, if you are struggling financially, it's definitely very reasonable to decline to give in that context. I suppose if anything feels "off" as well. (Though I wouldn't want to bias folks in the direction of thinking that there may be any reason to be more suspicious of people in need than others.) But over all, I do think it's something that can make a hugely, vitally positive change in someone's basic wellbeing.