Like most people, I am extremely uncomfortable when approached by someone homeless or down on their luck and asked for money.
That simple interaction brings up so many conflicting feelings that most people try to avoid it all together. I think when people say no or just brush the person off, most of that comes from their discomfort with the idea of poverty, their desire to believe that they are morally superior, or smarter, or more capable and therefore they themselves would never be in that situation, etc. There is also a valid concern that the money will go straight to drugs or alcohol, thereby sustaining that needy person's problems and ultimately harming them.
Once, I was extremely generous and giving. If someone asked, I would give money and wish them well. Over the last few years, I have become more self-protective, and with that, I often resent being asked to give to someone. I feel like I am already giving, that I have already given, and more blocked-up, fearful, upset emotions like that.
Now, I know that giving is its own energy. And money is energy in action. It likes to circulate and it likes to be given away. Blocking it up doesn't help anyone. Still, though, when asked, in the last few years, more often than not, I would just say no and keep going.
But now I have an excellent solution!! I do want to give and be kind to another human in need. And I don't want to feed any harmful addictions. So I have decided that I will buy Coffee Bean and Tea Leaf Gift Cards and keep them on hand. Most of the places that I get hit up are within a couple of blocks of a cafe. If I buy 5 $5.00 cards, Coffee Bean will give me a free drink of my choice. Then I can just keep the cards in my purse and hand one over if approached.
I win by being generous. The person in need gets a nice, hot cup of coffee, maybe some food, and a legitimate right to use the restroom. The business makes money. And I don't have to waste any more time averting my eyes or clutching my purse and my kids closer to me as we pass by.