<prompt> Human: My younger brother is 19 years old and has 20K of debt. I am 22, pretty well off, and have never been in debt. I want to help my brother, but I dont know how, or if I even should. I say that because he owes 20 of his debt to me, and I do not think he will be able to pay me back any time soon.Here are some facts about him: No college; no high school diploma. As soon as he turned 18, he was working 2 or 3 jobs at a time, which led us to believe he had a great work ethic. We grew up poor, so he splurged on himself as soon as he could and didnt save anything substantial. Bad money management at 18 isnt that surprising. We, the older sisters and I, advised him to be more careful with his spending; he didnt listen and continued to spend lavishly. We thought it was a phase and almost a rite of passage. Yeah, you worked hard, enjoy yourself! He convinced our eldest sister to sign for a car, and he would make the monthly payments None of us have ever gotten a brand new car, let alone, one that was less than a decade old!. He moved into an expensive, super-tiny 350 sq-ft studio apartment in downtown Yeah, it had a nice view, but it wasnt that nice for what he was paying and what he was getting. He bought a 50- or 60-inch TV, but he worked so much that he didnt watch TV; so he traded it for a 800 puppy. Its ironic because he was never home with the puppy due to his jobs. Despite his financial obligations, he cant keep a steady job. Its basically because he thinks he doesnt get paid enough to deal with whatever stress is specific to that job. We thought it was arrogant and entitled of him: What makes him think he doesnt have to start at the bottom and deal with crap like everyone else? I dont know why, but he was adamant about getting credit cards. Hes applied for 20 credit cards in the last year and even convinced me to get one! Dont worry, its a 500 secured CC. Considering how much debt he has, I dont think hes making any payments right now, thus tarnishing his credit score further. In May 2014, I lent him 3K half of my savings at the time and told him to pay me back six months later in November. I thought he was just going through a rough patch, so I lent him the money to avoid him having to take out a loan and pay high interest fees. In November 2014, when he was supposed to pay me back, he was still struggling financially, so I lent him 1K to pay rent and get groceries. I told him he HAD to start paying me back in January 2015. He agreed.Well, its already January 22, and I havent heard from him yet. At this point, I dont really expect him to pay me back. Its a bummer because I worked hard for my money, going to a job with which Im not 100 satisfied. I have financial goals, too. Things I need to do to improve my quality of life. The reason its a bummer is because part of me regrets lending him any money. Im not hurting for it, but it sucks to think that theres 4K Im never getting back. I could have been well on my way to maxing out my IRA contributions. However, Im sure my loans were significant and meant a lot to him, and hes just having trouble expressing it.Today, I received news that hes getting kicked out of his apartment and needs to be moved out by tomorrow Friday afternoon. I also learned that he doesnt have a job right now. It makes sense that hes been working two or three jobs lately because he wants to get out of debt. However, hes overworked himself, rendering him unable to properly cope with stress, and boy, does he have a lot of stress: Looming debt, incompetent coworkers. Im at a loss of how I can help him. I feel like hes not reaching out to any of us because feels in over his head. My eldest sister thinks he feels ashamed of his debt, despite all of our advice to be more frugal and diligent about his spending. I can imagine that the debt is eating at him, and thats why he didnt come around for Christmas. He probably couldnt bear facing us, thinking wed judge him. But its seriously depressing him and causing him to isolate himself from us, and that hurts me. I dont like knowing he is suffering.TL;DR: My brother is really bad at managing his money; hes losing his apartment and car. Ive lent him money in the past, but he shows no signs of paying me back any time soon. I feel like his 20K of debt is eating at him, causing depression and isolation from us. I dont want to give him more money, but I just hate to see him suffer. What can I do to help him? Edit 1 - 8:15pm CST: Thanks, everyone. I knew I could look to you for solid advice. Heres some additional info to help you better understand the picture.To quickly address select comments: unaksidras: I think he realizes how much he is in debt and doesnt want to dig himself further, so thats why he didnt tell us about missing his rent and car payments. uPotatoAvenger: 1 for your name; I love potatoes. The puppy is going with one of his friends. utracygee: We know that not all of his coworkers had to be that bad. It was too unlikely considering all the places hes worked. I think his stress stemmed from the realization that there is no perfect job, not everyone is a Spongebob worker like he is, and that some people get paid more just because they have a diploma or a degree, even if their work ethic, knowledge, or ambition is inferior to his. Our mother: Raised us by herself. We respect her for that, but neglect and abuse were rampant in our household. Drugs and alcohol were involved. It messed us up in our own ways; so none of us have a healthy relationship with her. When we were old enough to move out, we became financially independent of her. However, she reached out to each of us on multiple occasions to borrow money, promising this would be the last time. Theres a mixture of reasons as to why we let this go for as long as we did, but we eventually made individual decisions to cut ties with her and not really include her in our lives. We had given her plenty of opportunities to make things right, and enough was enough.As for my brother: He will be staying with my eldest sister, and shes implementing ground rules, such as getting his diplomaGED, as well as keeping a steady job. The dog will go to one of his friends. I will be taking over the car payments and of course, driving a brand new-ish car!. Ive calculated this to be an additional 100 expense each month if I drop my current cars insurance. It works out because I was actually wanting a Civic before I bought my Accord a couple of years ago :D We will recommend he seeks a psychological health professional, as well as a financial counselor.One sister has offered to put all of his credit card debt in her name since she already has student debt. Its awfully generous of her, but at this point, we are all concerned about him and do not want to lose him to what looks to be a mental health issue manic-depression may run in the family. Right now, we are not worried about the money he owes us. Instead, we just want him to know that we are here for him.  <response>: DO NOT give him another cent. Hes not at bottom yet. Hes nearly there, but if you bail him out, he wont learn anything. No, he needs to hit bottom and you need to wait for that. You give him money, he will know family will bail him out of any situation he gets himself into, and will not learn consequences of his actions. Tell him he already owes you money and while its difficult, that this is a hell of a good kick in the ass and he needs to lie in the bed he made. Youll know hes ready for serious change when he rents the cheapest, tiniest, grossest apartment in the worst part of town, keeps working those 2-3 jobs steadily and with little complaint about his incompetent coworkers. Which I seriously doubt they are, I think he just wants to pawn his work on them and they arent taking it, or else his coworkers are reacting to his own screwups which are taking time from their jobs, making them look incompetent Also when he gets over himself and stops acting like hes some special snowflake that deserves the world handed to him for working. If he has to spend a year or two couchsurfing and homeless and alone to achieve that, so be it. Thatll be his getting out of childhood lesson. 