Men, what would you do in this scenario?

Let's say you are a homeless college student. You have a part time job but you can't afford a hotel and you still have to pay for college. One of the guys you are friends with is very kind, charming, and tells you that you can tell him anything and he'll never judge you.

He also says he'll buy you something to eat for free and you know that he wants to learn more about your family and current living situation.