Mad respect, as someone who puts in about 400hrs at a shelter per year

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I'll say this though, try to give resources not money. If a person says they're hungry, offer them food. If they tell you what they need see if you can accommodate in anyway. I gave away some old shoes (single pair) cause his shyt was like
Dude was probably the most appreciative person Ive ever met in my life. They were just some shoes I didn't wear anymore and was gonna mow the lawn in or throw out.
Give food or old clothes. I could type a novel based on my career. I deal with these people daily. Cash is a quick way to close an interaction but its not the answer. Your funky lil $10 has never helped a person finally have enough to put down the deposit and first months rent on an apartment, or get a room for the night to stay out of the cold or rain.
Once money goes, its gone. If a guy is standing outside of the grocery store dont give him $5 buy him a loaf of bread and a jar of peanut butter and jelly. He can eat sandwiches for days and it wont cost you much.
You have a right to know where your money goes. Ask what is this for? Then you can see how you can accommodate. Like above, dude might say he wants "shoes" or "gloves" or "a hat" you can easily buy them shyts at gas stations, grocery stores, dollar stores....dont give them the receipts either. We're far too busy to watch these dudes but a lot of these cats are parking in the shopping center and walking to the intersection and holding a sign for hours then walking back to the car and going home. People talking bout "Im just trying to get money to get on the bus to go back home to....." 3 weeks later they are still in your city/state. Dont get finessed or just give your money away to feel good for yourself. ensure that your helping someone for real. Its a simple process once you do it enough, its not a long interrogation and hearing a life story. Its usually very quick and simple "Do you have any spare change?" "For what?" "I just want to get something to eat" "Whatchu want?".