My brother is a 99er... should I give him more money?

First perhaps it hasn't hit oyou but the economy does in fact suck, it is hard for everyone. There are lots of people who are out of work trying to find jobs. So you option c is just you being a jerk. I'm not sure why you feel the need to beg him to pay you back later. If all he has borrowed is $135, that's nothing. loan him the $150 or make yourself feel better about it and don't loan it to him, find jobs around your house that need to be done that you do not have the time for, pay him for doing those. That way it is not a loan but payment for services. And he doesn't have to feel guilty about owing you money.