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If you're advising him to file for bankruptcy for $3500 then I really don't think you should try to help this guy out.
First off, no one should be helping him pay for his debts. Go big or go home. If eventually the road will lead to bankruptcy, your friend should apply for more cards, get higher limits, and max out on whatever loans he can get. Your buddy obviously has no assets to worry about.
If he really has psychological problems then it would be hard to convince him of doing the right thing like what SkinnyPupp suggested.
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