>>3040684I have a few questions for context:
Is this in a small community that I care about, and he is a local? If so, I immediately offer to take him to get some food, find a place to help him sleep better, perhaps offer to buy him some supplies, etc.
Is this in a big city? Ask him how he doesn't have enough money yet -- is he on drugs? Does he drink alcohol? If so, then he isn't getting money. At best I'll buy him some shitty cheap meal.