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Moving into a new neighborhood with my girlfriend. We each lived in different parts of town and worked different schedules, so each arranged for separate moves. I had just finished unloading my stuff. Friendly neighbor walked over to say hello. We started chatting. Nice guy.
At some point, he mentioned something about having to head home for a pizza party. Checked his wallet and he was short. We all know where this is heading so I'll skip to the end. It only cost me $40. Never saw him again.
Lesson learned.
When I was younger I read somewhere “If you give someone $20 and never see them again, it was probably worth it.” Accounting for inflation I think that perfectly fits your situation.
I moved into a new place, there was a tenant in private suite downstairs.
We hung out here and there and I fronted him for a couple restaurant meals over a few weeks.
When I started asking for him to pay me back he laughed and said no, you shouldn't give money to strangers.
I let the landlord know, he didn't care, we stopped talking and I eventually moved out.
Lol, I'd rather be a nice person and short $40 than a jerk to every new friendly person I met.