I'm guessing that the question was so inappropriate that OP thought that only someone who truly needed it would do something so inappropriate as ask. Normal people would have to overcome a lot of embarrassment to work up the nerve to ask such a thing, so if they've managed to do so, it's not crazy to conclude that they must really be desperate. And if you're on good terms with the person, you probably won't see the harm in giving them a couple bucks on occasion.