It ain't on me to judge you or your journey to asking for money on the street, but here's a few tips for success if you're in that boat and we cross paths.
  1. Be honest
    It's hard for me to tell which people are in legitimate need and which just own an ugly dog and don't want to shower or pay taxes. So if your pitch hits home I'm much more likely to pitch in. The second-to-last person to score a handful of change from me just said, "I wanna go to Wendy's." So do I. All the time. Here is money.
  2. Remember me
    We can be friends. You don't have to know my name, but I wanna know yours, or at least get a visual cue of some kind that you recognize my ugly mug. In the last place we lived, my friend M——— slept in a stairwell between the subway and my work. After a few short but enjoyable conversations I started leaving a coffee in the stairwell on days I didn't see him after my breakfast at McDonalds. I hate coffee, but it came free with my meal, so it was an easy share.
  3. Take "no" for an answer
    Unless you have the four children mentioned on your sign surrounding you, I'm always going to wonder just a bit whether you're taking artistic license with your cardboard that claims as much. But that doesn't mean I don't want to help. Sometimes I just don't have it. When I do, it's yours, but please respect me when my own responsibilities and expenses feel too heavy to ignore once in a while.
  4. If I'm eating, get lost
    Do NOT approach me while I'm eating. Ever. I'm using that time to relax, think, and/or spend time with people I don't see often enough. Interrupting those activities is an automatic shutdown.
  5. Just ask
    The magic words: "Hey man, can you spare any change?" It's a yes or no question, it's easy to answer when I'm in a rush, and it's not BS about needing a bus ticket when the buses are free where we live. The sob story, especially when it's the same one you told me last night, just takes us both away from earning the cash we need.
  6. Accept credit
    I hardly ever carry cash, but let me buy you something inside the gas station or restaurant. If my request to do so offends you, then I know my money was just going directly to booze or drugs anyway, and I don't play that game.