I listen to stories, I don't question them...
"Can we take you to a shelter tonight, it will be about 2-degrees later this evening with a windchill in the negatives," I asked? He looked down at his sign as if to think about the question, then held his sign up. It read, "I need money to buy diapers for my son."
I said, "You don't need to stay in a tent tonight, you will literally freeze to death." He said to me, "I just need a few dollars, I have to buy diapers for my son. He doesn't live with me, he lives with his mom in an apartment - but I have to buy him diapers... diapers... can I have a few dollars?" I said, "I'm not here to hand out money, I'm here to take you to a shelter so you don't die tonight in the cold." With a trembling tone due to the cold he said, "I'll be okay, I'll be fine... I just need a few dollars."
I told him to call the police department if he changes his mind about sleeping in the cold, informing him that they won't ask any questions tonight - they will simply take you to the shelter.