Hi everyone... I've a few personalities here. They are my friends, neither best, neither worst, just meeting sometimes. My point of view won't change on then, whatever you will write, I won't get insulted either.
That's some long read, requiring a big and explainful answer, so if you are not going to answer, please don't even read it. 
Here's what I think: They may have some psychological sickness (Yea, psychological sickness sometimes is for ruining lives, helping relatives and naming things you do, but anyway), also I've my ideas about their personalities, etc.
Question: What do you think about those personalities? What can you tell me about them? And do they have any psychological sickness? Would be nice some long, nice and explainful answers.
P.S. I know, that it's hard to determine with no meeting the person, but from how he acts, is that possible, that he has some psychological sickness?
These speculations are taken from talking to them generaly, being friends with those people and by talking about some of these things, giving random questions for example. I'm not using emotions while writing this text, so it won't be any "emotion driven" context.
Your answers are for making sure I am right (good in psychology), or I am wrong (not very good yet). At determining peoples' actions.
Your answers should help me get better in psychological examination of peoples' personalities and actions.
Your answers are for my own interest about these people. Getting know them better, if I am not right, and if I am right about some things.
Personality #1:
From the side he looks like he doesn't care about anything. You can tell him anything, and he wouldn't care. Except for reputation. If someone would disrespect him, he would disrespect him triple as much. But that's only if it's in public. In person, he cares only about very bad things, that you do to him to disrespect you.
If you ask him for let's say some cookies that he just bought, he will share. Always, or near always. He can even buy you some cookies, if he's in a good mood.
He looks like a caring guy sometimes, when speaking in person, or doing things in person. Fair that way, but not very fair when near others.
He likes to piss off people sometimes. Usualy when in a bad or not very good mood. When near others - almost all the time.
He tend to think, that he is very respected (he is, but by younger people around him, his best friends - 15-17 years old... And he is soon 19.).
He thinks, that everything will turn out good. He will figure it out somehow. Even if the thing is least likely to happen. He just doesn't care about what happens. If it fails - he thinks, that he will figure it out.
He is pretty smart. I would say around 110-130 IQ.
When you are alone with him, he is like a very nice person most of the time, nice to talk to, story telling, discussions, etc., but when he is with other friends, he often pisses people off, especialy those, that are not like most of those other people. Example: he is with 3 of his friend, and 2 other, very stupid guys. They sure show their stupidity, but even when they don't, they are sometimes being pissed off.
When he reaches their "barrier" and they say "i go home now, go f... yourself" or starts to cry from physical abuse (very rare, usualy from another friends, not from him), he starts to convince them to stay. Then he stays calm until they get calm, like ten minutes, and then again he pisses them off.
You cannot convince him to do anything, he do as he wish. He wants to go smoke pot - he will do it, even if he's told you, that he will go with you somewhere. (just an example)
He is not in a very good relationship with his parents, because he wants freedom. He is free. Parents can shout, take money from him, do whatever, he doesn't care. Parents knows he's smoking cigarettes and drinking (~95% people do that in this country, so not related anyhow). They cannot do anything, he doesn't listen. He doesn't learn good at school, parents cannot do anything. Just some examples. (not of concern, just examples)
He often is scared of being intellectual, because people around here doesn't like intellectual people, so he's being an a** instead.
He likes cats and some other "sweet" things, but he is scared to show that, since it's a sign of weakness, emotionaless and sweetness.
He is a good person deep down, but on the outside, he is not often.
He makes rational decisions often. As I said - he can promise do something a week ago, but change it the last second.
He doesn't think much of the consequence. (Not sure about this, but it seems so)
He doesn't care what people he doesn't know think about him.
He doesn't believe in god, doesn't like authority figures much, likes to not be controlled by someone.
He has money, he doesn't keep them, he spends them for his pleasure.
If he needs something big, he has difficultes getting the money in one place.
Sometimes he buys something big and after a month or two, he doesn't like it. Then he resells it for double lower price. he's bored. Or he keeps it for a few more months and then sells.
He is not very caring about his health, not washing hands, drinking from the same bootle with homeless people, etc. (for buying a beer for example, he used to give homeless people a sip of it)
When he is doing some activity, for example playing some game on the computer, he often gets bored of it, then stops. But he doesn't like that he got bored, he would like to play, but it's boring for him, even though it's interesthing and seems nice to him.
He has different people, for different purposes. Some for talking, others for drinking or hanging out. Other guys for playing certain games online.
He's a good lier and simple lies determination, but not advanced.
He can forget about a person for a year (happened to even few persons he know), and then come back. Even if they are in a very bad relationship condition. Come back, straithen things out, but never say sorry. And then continue old activities with the guy.
He never says sorry. He always blames others, or makes a joke to get away from the question, or uses treatening to the person, who's asked the question of him.
He is not very careful with things, like running trough the street, when there's cars nearby, etc.
He is treated with respect by those kidos, and other people he knows, because he drinks, he doesn't show fear and he smokes. Drinking and smoking around here makes a big role in boy's life and respect. From ~10-12 years old. However, he is not respected by his parents, because he doesn't listen to them. He is being treated good though, parents brings him food near computer, gives lots of money, etc. But he is not respected, because parents often (probably about every evening) says bad things to him. He doesn't pay attention though. He is not very nicely respected by the authorities - teachers, because he shows as a bad person near them, because he is with friends.
He listens to a few songs only for the last few months - "don't worry, be happy" style, which could mean, that he is sad for some reason. Although, he often is very happy. Like 4/7 days happy, other three days he is angry/sad.
Okay, I think, that I've told everything about this guy. Since there's a lot of information, I thought, that I will create a new topic about other personalities, after this one is answered... If you have any further questions - ask.

And don't hesitate to write bad things too, as I said - I won't get insulted or anything else.
Thanks!