Friendships - Like trying to mix Oil and Water...

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I'm not sure if this belongs in the Friendships Forum, School Life Forum or maybe even the Adolescent Forum, but I felt I should post this purely to seek advice and opinions on a rather smallish problem I've been having that has been constantly annoying me for the past few months.

I'll put this rather shortly, as it is, in effect, a rather short topic of conversation. Basically, there's this person in my class that shares so many similarities to myself - cold, calculating, shy and obedient - yet I cannot seems to speak to him at all unless there is a common friend between us that we both spend time with. This is where my rather ingenious title is involved - Water and Oil can only merge if there is some form of Binding Material involved, otherwise, they will merely keep separating from eachother. This is much like this issue, where as, with a friend, we speak for pretty much the full hour; yet, without one, he stays as far away from me as possible - and I am somewhat fearful of him (mostly, other than the Social Disadvantages caused by Aspergers, for the reason that he actually shares so many of my own traits, and I know what such a person is capable of as far as cunning is concerned).

The problem is, he, like his friends, is not the usual disobedient, unruly student that the majority are. I have, for a while, tried to befriend his friends - with no real luck other than finding out that I am completely shy when trying to speak to them. These unique traits that make him so very similar to my true personality are angering me day and night wondering why I can't seem to speak confidently to that group of people... Therefore, I turn to you - Oh, great Aspies of this Website - to help me out on this rather difficult social problem. I know there's no real answer other than "Speak to them", but I merely post for advice on how to do so.

Any replies whatsoever? If not, I think I'll try to use various online methods to contact either him or his friends and get to know them better. That should, at least, get rid of any thoughts of me being an idiot due to my lack of social conversation.

I've a friend who is in some ways a lot like me and yet I can't seem to have a sensible conversation with him. so I can at least somewhat relate. I've no suggestions, though.

Well, this wont be easy, talking to people is always difficult.

Perhaps you should find some "common ground", something you're both interested in and then start a conversation. Either way,it'll be difficult.

Apparently, after talking to a few of my own friends, they say that he'll talk to anyone who talks to him but he never initiates conversation himself - just my luck... As for common ground, apparently his father is a semi-successful businessman that owns a pub (then again, that could just be a rumour - as apparently he can't afford to pay for private schooling). I've been asking these friends constantly, yet they can think of nothing else other than that small thing.