Anonymous wrote:OP here. Thank you so much for the response! I fell lost, and I more importantly, he does, too. He obviously needs someone to care for him. He is able to do holidays with some local family close to him, thankfully. But they are not in the position to look after him.
He has asked me for money for rent before, and I have refused, because I think his choices are terrible. He has not had any guidance or inclination to figure out money himself, and his priorities are terrible. For example, in college, he was living in a pristine address, while he could not afford his tuition.
He does have a job, but rent has always been a challenge to him. Right now, he lives within walking distance to work, and the absence of a car payment or expense works for him, so we need to keep that situation. I need to help him without enabling him, given the circumstances.
10:43 here. You are on the right track about helping vs. enabling. You realize his shortcomings.
Maybe if you help from a perspective of focusing on guidance/mentoring vs. mostly providing financial support, that will help you find your way. Sure, people like your nephew could use the financial help, but in all likelihood, he probably really needs a relative who will be there for him long term.
His knowing that you are someone that he can depend on for emotional support and motivation (and occasional financial help if necessary) might be the most fruitful way to aid him.