I have friends and family members that constantly throw money away, then complain about lack of funds. I used to try to help, and eventually realized they didn't want that. Now I say, "Oh man, yeah, that sucks!" Or, "Ah, cripey." Or, "I understand: You really, really wish the province would give you a bus pass without having to do paperwork first." And that's all. It ends the conversation in a peaceful way. They know I can do stuff, they know I'm willing to help when they ask directly for that (same as I teach my kid to do). I don't offer help upon a whine, rant, etc. I reflect back, or murmur compassion. They feel better in the moment, which is all they wanted. If they ever ask me for help, I will give that. But even then, my first question is, "What are you willing to do?" They screen themselves out of most options; it's best for me, though, to know that before I invest a lot of time and effort.
Never do more for a client [friend, family member] than the client [friend, family member] is doing for himself.