Differing opinions within the system

Long story short, we have a (also system) friend who has struggled with money and finding stable places to live for some years. He has asked me for money a number of times and usually I oblige. Not always but it’s 10 bucks so why not? 

He always swears he’ll pay me back but we both know he won’t be able to. I don’t expect it; it’s a gift from the kindness of my soul and sometimes people need help. It’s not like he doesn’t share his nice things with me when we hang out or anything, he clearly does his best, just doesn’t… Really have….. Like, almost anything.

If it were up to me and money were no object, I’d help him a lot more. But he can use my shower or laundry room if he needs, so I feel like I’m already doing him many favors.

It’s hard to write this because, in our system there are differing opinions on how to handle this situation. I (indigo) would love to get him out of his financial hole if it were possible. Matt is okay with lending but gets very annoyed when we don’t get paid back, even if we didn’t ask to be repaid and had the choice to not lend it at all.

Ok I’m going to type a little, sorry to interrupt, but let me explain. It’s not that he doesn’t repay me, it’s that he keeps promising he will like I’m on his ass every time for the money (I’m not and never have been even when maybe I should’ve been). I also am tired of giving out things just because someone else wants it. Of course I want him to be doing well, but I’m not Jesus and I can’t make it happen for him and clearly NONE of his other friends can spare a penny so why should I take all the weight? We already offer him so much and now he also wants money. It’s not a big amount but the principle of it keeps tension in the air, and that’s just going to bother me. Plenty of times in our life we’ve been taken advantage of for being expected to (or too stupid to avoid) fix other people’s problems. We’ve struggled with money as well and are only just now at a point where we know we can afford rent without worrying too much.

I want him to have the money, I just don’t want him to keep asking us for it when his partner won’t get a fucking job, his roommates are very irresponsible and bad with money (also I don’t like them!). I just feel like he’s made some choices himself that put him where he is and somehow thinks those choices aren’t at least contributing to his situation. Maybe that’s just the bitterness talking, and it’ll all smooth over, but we cannot offer him any money, which we haven’t been, and we also can’t lend him any more even if he really needs it. I’m sorry, but I’m also no one’s Messiah. 

It’s a point of argument but I guess the solution is just to not agree to give any more money. We give him so much already, extra skin/hair products, shoes that he might like which were gifted to us but 3 sizes too big for us, it’s a fine way to get rid of stuff we won’t use but he will. It’s just the money thing that needs to be paid attention to in the future.