Most Helpful Girl
You teach others how to treat you. You're accepting the behavior of the guys who never offer to pay or go half with the bill. If you don't want to date men who are broke don't accept a date with him.
Keep in mind it should be more about the reason he's broke. If he's lazy and has no ambition to work ditch him. But if he's a struggling student then figure out fun stuff to do that doesn't cost lots of money.