Honestly, I wish there was just a way to break the cycle of deceit. I hate the feeling of prying into why someone needs money and even detecting whether it is a "worthy cause " on my part. The way I see it, someone is asking for money typically because they need money. Like, hustling/panhandling is not steady/reliable/repeatable to a degree that you can do it forever as a means of income and maintain a normal or healthy lifestyle in any way. You do it cause you have to (albeit there are case studies where I'm sure someone has done otherwise, however, this far from the norm), but you can't really just tell someone "I need to pay back my credit on my pill habit" or "I need a fucking 40 so bad I'll totally do this humiliating thing until I am numb to the effect it is having on my psyche, thanks due, in turn, to the liquor itself" or "I have undiagnosed and untreated schizophrenia/bipolar disorder/substance abuse issues and I need money just acquire basic necessities". The only times these transactions have ever gotten aggressive are when they were aggressive from the get-go, they have never "turned" aggressive in my experience. And I, as a smaller, fragile enough looking "faggy" white boy, definitely get accosted aggressively more than most.

I pretty much just adhere to a couple rules that have done me well:

-No sob stories. I just shut them down. If someone is doing a long, dragged-on thing to eventually influence me to give them some money that didn't seem like it at first, I just say "hey, you coulda just asked, but now you've wasted my time."

-max $5. that's it, just give it and walk away, maybe with a "Good luck and stay safe".

- I will buy you food or some direct resource. Just be cool about it.

-You're never an asshole, neither of you. You are both caught in the maelstrom of influences that is outside of your control that manifests itself into the scenario, and you absolutely retain the right to not participate.

I don't have much input for someone with a kid, though. I would take faarrrr less risks if I had a 4-year-old right there depending on me, especially if someone walks up to me with my back turned. Maybe his story was true, but so was yours.