I should add... I'm not the only person helping him, although I'm the one who's handing out more money. His family puts in small amounts of money every now and then.

They too have a history of bad finances. A long time ago they used to be quite OK, living in a very nice neighborhood, going to private schools and such. All of their friends are reasonably wealthy people and they like to live a good life with a live-in-the-moment mentality, which was an issue for me because I come from a humble middle-class family that was wise enough to have long-term goals with their modest income... and I'm proud to say that my parents' future is quite sorted out already now that they are about to retire. Well, something went wrong with my boyfriends' family business and they pretty much lost everything, and they have had quite a hard time recovering from it. Both parents have weird priorities, which worries me too, even though all of this hardship has taught my boyfriend to really think about what's important and what is not, so he has been making a real good use of the little money he has and says this is a valuable lesson for him and his future.

Anyway, he has ADHD with a tendency to depression. He talks a lot –and a considerable portion of it is not entirely realistic–, but has a hard time taking action. Might have a very mild bipolarity? Last year, I was feeling sort of happy that we weren't fighting anymore, but I noticed he would spend the whole day lying in bed in the dark with closed windows and wouldn't talk much, ... he truly looked miserable. I know he feels lost and overwhelmed with the amount of debt that he has, with his inability to make a career out of all the money he invested on his education, and the guilt of ruining his family's credit with his student loans, and the ongoing money shortage that his parents have. But again... I cannot solve this. He always sees me as a privileged person, and I feel he is always going to see me this way as long as I have more money than him, even if it is just $100.