I give help with the specific items they tell me they need or gift cards to the grocery store so they have money for food.

Maybe give them a gift to a money managemrnt course so they can learn how to manage their money better. There can be a fine line between helping & just enabling them to be irresponsible. Even our local place that helps people with financial needs sits down with them in a financial counselling session to really analyze the problem.

Any time this happens more than once you have a right to question.