Originally Posted by patrickBOOTH
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?
Hand him a referral card for a local homeless shelter. This is actually what homeless advocates suggest that you do, so you're on solid ground. Plus, after you give him one, he'll never bother you again.
In the alternative, you could just pay him to follow you around carrying your overcoat in case the weather turns.