Predicament to run by you all:
A few weeks ago this guy I see riding his bike a lot in my neighborhood pulls up to me on my block and says, "Hey man, I see you all of the time in the neighborhood. You're always dressed up, I'm so curious as to what you do for work." We had a pleasant conversation. He was a bit scraggly, but it was warm out and he's a hipster so I didn't think anything of it. Now, I see this guy begging for money at intersections and such. Naturally he sees me, knows me now, and is all, "hey man, could you spare anything for me?" I literally didn't have any cash at the time, but I felt kind of like a dickhead. The issue is, I am seeing this guy begging often now, I feel like if I give him something he's going to try and hit me up for money constantly, but not giving him anything I feel bad given our short conversation. I feel hostage on my own block.
Do I never give him anything?
Do I give him something every time I see him?
Do I stagger when I "have cash vs. not have cash?