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It is very hard to turn a person down who comes to you for help. I am suprised with the advice given so far- in that it is pretty damn good.
1) If there is a substance abuse problem, this has to be rectified before anything else can happen. Seems everyone here who has been through it agrees. Don't they have places where you can check in for free and get help/counseling as well as room/board for awhile? And, as people here have said, if there is substance abuse, there is underlying psychological turmoil at the roots. He needs to kill the roots.
2) At this point, you will have spent nothing, because the program was free. As for a job, making a recommendation is totally cool, so long as you tell the potential employer the truth. Also, a really cool thing would be to have him 'interview' with the guy, even if its a shoe-in. A boost in confidence from this would benefit him I think. So just tell him you can get him into an interview, and the rest is going to seem more gratifying to him.
3) Assuming a job is in order, it shouldn't take long for him to have enough $ to at least pay rent and food. So at this point, you could feel comfortable with a 2 month expense loan. Set a really easy timetable to pay it back, like a year with the payments spread out and starting in month 3.
4) The weekly brunch idea is fantastic. Once things get comfortable, maybe even try something light such as bowling or something. Just to keep it light. This gives the guy opportunity to speak about individual problems that are cropping up, so you can make suggestions about reasonable and non-criminal ways to handle them.
You're a good guy, as I suspect most of us are (scary, isn't it). Lending a helping hand is the right thing to do, but you can also do it without putting yourself in serious financial risk. And besides, I am certain that just throwing money at the problem will probably make it worse anyhow.
Best of luck to you. No matter what, I bet there are some big bumps in the road ahead.
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