I live in Boston (and occasionally NYC) and I rarely give money. My grandfather taught me to rarely/never give money, but always buy any person a meal that asks for it. And I've done so on several occasions; taken someone to a Subway or whatever is nearby and bought them food; or to a 7/11 where they could purchase whatever food/toiletries they needed. Especially in the winter around here, being outside like that all day is brutal.

I have had a few occasions where people ask for money for food, and I tell them I'll just buy them food and they refuse. But I've had many more times where they are excited about it. Generally they ask for very little, sometimes just a cup of coffee and a bagel.