No matter how much some little things try to frustrate you in life, I think it's best to learn to let stuff go. When you put yourself in a situation of just trying to make an earning on your own and then accumulate some debt from school, I don't think you are at fault for doing it. We also all have some spending needs sometimes. It's just really important to not to go on a binge of some sort. It's great to help out the needy, to extend out our reach and time for them.
You know what, women may be different from a guy but it's not like I'm not naive enough to not be able to handle them as good friends. To not to really be in their way or try anything bad and if there needs to be something done with them, just talk in an encouraging or concerned manner without trying to bug them or annoy them. They may do this to you sometimes based on the relationship they want to take upon with you, but being a man with a big heart is what my mom seems to really enjoy being around.