I know several people like this. One of them is a little older than me (I'm 32, and he's 39 or 40) and he does the exact same thing you described. Goes to work, complains that no one helps him out, then when you help him out you missed something or didn't do it right, and when you tell him to get bent and stop helping him, he's right back to complaining that no one helps him. He does the same thing with women, and then wonders why he can't keep one around. He has kids that don't want to live with him, because of his behavior. Its hard to tell where the line between genuine mental illness and just being a jerk is. The best thing your friend could do would be to seek out professional help. The hard truth, though, is that you can't do it for him. If he wants help, he will get it. If not, well... you can't carry the world on your shoulders.