I wonder if the people saying they give money every time live in major cities (and walk often).
If I gave a quarter to everyone who asked me for change, I'd be out over $200 per year. Double that if they're still going to ask me on my way back (which is likely).
Some of them would also be rolling their eyes at a quarter. Some panhandlers can even become aggressive if they don't like what they get.
I'm not going to say that these people are going to waste the money on drugs, though some will (and I don't care what they do with the money, really). But I'd rather...
- Donate that money to food banks and other causes
- Not carry around unnecessary change
- Not risk pulling out my wallet in the city (in case I forget to keep the change handy)
- And NOT turn city sidewalks into tolled walkways for people who can't afford a car
As for what I do? I do the hand thing and apologize. I make eye contact (or at least look their way). If they ask again, I tell them I don't have anything. There's no reason to feel shame for not giving. Like someone else said, it's a numbers game.
If there are regulars and people who are genuinely down on their luck, then (if you have the time and willingness), you could talk to them, and maybe offer to buy them food or something.
Of course, there's always the chance that they'll bring the food back and ask for a refund. But hey, they would've used your $20 the same way.