I've got a buddy I really wanna help out

This dude is socially ackward to the max. It pains me to see this kid try to hold a conversation. He lacks an identity, just feeds off of others around him in a needy manner. In a nutshell he comes off as an over-compulsive coke head. Normally I'm one to let others find their way, because I'm still busy finding mine, but I really feel like I can learn by healing him socially.

What I've observed so far:

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  He lacks power when he speaks because any statement he makes towards someone is in the tone of a question, or is actually worded as a question (i.e "We do some dumb shit don't we?") It is so fucking needy, its almost as if his actual belief system depends on my answer.


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  He often questions his own personal performance, as if his self judgement is not good enough (i.e Hasn't my acne really cleared up lately?, aren't I getting good at math?, aren't I better looking than him?") 


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  He gets over excited. It's not charisma though, its not peaceful, or acceptance of the moment. Its fake joy, coming from his outcome dependency. He see's an exciting opportunity and becomes depedent on it. This is almost always accomplanied by crash and depressed state of mind. (i.e He's excited because he hears girls are coming over, he ends up not having fun with them, bitches for the rest of the night.) I still don't fully understand this behavior.


• 
  He has compensated for his lack of social skills by building physical skills. He is always down to throw his fists up, but is extremely passive in a verbal conflict.


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  He has a strong creative mind, but it almost always is used in a negative way. He can describe his perfect life detail by detail, but then tells himself he is not destined for it. He is not destined?! What the fuck, you can have whatever you want, you make your destiny. This is what really ticks me off, because he doesn't understand this. ( i.e- real message- " I'd love to have a life like yours. Your gonna have a high paying medical job. One day you will come home and be mad at your wife, then you will rememeber that I'm gonna be overseas watching my friends die you will remeber how shitty my life is")


• 
  He has trust issues from his parents divorce. pretty common I guess. This is what makes him needy. The thing that worries me is he shows signs of schizophrenia at times. Telling me he has a "Voice in his head telling him not trust anyone". Not sure how serious this really is.


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  He uses guilt to make people accept him (i.e " Dont worry about me, I'm gonna be dead by 25 i'm going into the army")


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  He lets the external world play him, instead of being the creator. He lets life live him, opposed to living life. He thinks things are concrete and definite, that certain things such bad grades make him destined to be a failure.He thinks he's a shit head, he tells people he is a shit head, and takes on the persona. ( i.e -real text message-" Stop trying to help me and lead me into the wrong direction. I'm a lost cause, a fuck up, and a hot head. I look for fights and like hurting people, I know I should see a therapist for it but i kinda like it")


• 
  When he is in the limelight, he does a complete 360 and becomes an overconfident douchebag. (i.e girls comeover his place, they are friendly because he's the host... he gets excited and starts trying to fight smaller kids)

He is so thick skulled and I can't seem to get into his head. Does anybody know any SUPER BASIC literature I can throw at this kid to help him out? Anything like Tolle would screw him up even more.

I apologize for all the writing, it was tough to keep this concise, but please give it a read and give some insight. I just have to much empathy to let the guy loose.