It seems to me that conversations have different levels that are obtained in sequential order. When people initially meet, they grab the first rung of the ladder which is social chat; chit chat and the like. Nothing of any depth, just conversing about whatever. Like two boxers eyeing each other up in the ring…circling and throwing the odd, testing jab to see their opponent's form, style and reach. During this stage of conversation two people get a gauge for if they like each other and how much they enjoyed each other's conversation and general countenance.
If people are driven to spend enough time with each other, or if they just connect strongly enough, they move up to the next level of conversation where things are more meaningful. They may discuss on their opinions and views of things, now safe that their companion is sympathetic to their views. They may be more candid about their life situations, or they may discuss in detail about the things that interest them now they know their companion is reciprocal. As people tend to like people with similar interests there is more range of things they can talk about in a more in-depth manner. If sense of humour is similar then they can add a humorous angle to their experiences, or bring something into conversation purely down to the fact that they found it amusing. It is from these types of conversation that lasting friendship can spawn.
The thing about me, and I guess most people with Asperger's Syndrome, is that I am actually a socially boring person. I'm not a boring person, I can converse in-depth and with articulation and knowledge on many, many topics. I also have a pretty good sense of humour and can throw the odd joke or humorous observation into most topics. When it comes to the upper-rungs of the conversation ladder I can hold my own along with the best of them, I just can't handle that first step. If a stranger were to come up to me and attempt to spark up a conversation they'd soon find themselves frustrated and bored, as general meaningless chit-chat isn't something in my vocabulary.
As you can well imagine this is quite frustrating. I know I'm a fairly decent guy with a lot to offer, but no-one else does. Not through any fault of their own, but mine. I have things to say and discuss and talk about but no-one to really share my thoughts with. I realise I give off an impression to people that I'm curt and uninteresting and I suppose in these initial moments of meeting they're right…I am a socially uninteresting person.
Even though I can converse at those upper rungs of the ladder, I myself still can't instantly jump there. I can't approach a stranger, or have a stranger approach me, and converse on higher subjects right away; I too need that initial phase where you get comfortable with people, but for me that stage involves much less conversation :) So how do we get past that first rung of the ladder? How do we convince people to persevere with us? How can we drag them to our heights? If I had the answer I'd bottle it.
For me anyway, two things do help. First is working with people via your job. That way you're forced to be around each other and spend time with each other. In this captive situation you can conduct the "getting to know you" stage at your own pace. On-line situations also help where people tend to be in the same community due to a shared interest, and again you can get involved in a level you're comfortable with.
I mentioned the frustration before; having all these things inside you that you feel are going to waste. But the other aspect of frustration is when other people insist that you "just need to come out of your shell" and "stop being shy". I have no shell and I'm not shy. Yet again it is just that our worlds don't align, that I'm a square peg trying to fit your round hole because your round hole is what is considered to be correct.