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SilasBarta comments on How to always have interesting conversations - Less Wrong
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I think that one of your main problems may be that you're thinking of conversation as something it isn't. There is no procedure for success. Genuine conversation is procedure-less (or at least practically so. I guess with sufficient processing power and knowledge of all the hundreds of variables you could replicate it, but I think such a feat would be beyond the abilities of the conscious mind).
I used to be extremely introverted. I found talking to people I didn't know very awkward. Even moderate acquaintances were tricky. Then I went to university and made some new friends. Went out. And then just decided to talk to people. Alcohol helped. A lot. Now I am what many would call extroverted, though I still feel, in many ways, like an introvert pretending to be an extrovert.
I don't think there is really such a thing as introverted and extroverted people at all. People are encouraged to think of these things as part of their "essential character" (TM) - or even their biology. And in some medical cases, this is obviously true (such as in autism).
But for most people, it's not a lack of ability, it's a lack of will. People think about worst case scenarios. They think about (as you mention somewhere else in these comments) weirding out a load of people. And maybe you would. But the key, I think, is then to disregard your fear and just talk anyway.
The idea of an extroverted social animal who feels no fear is a false ideal, I think. Everyone will have jokes that fail, everyone has conversations that, the moment they start, you know that this person is really not for you at all. What the "extrovert" does that is different is simply to keep talking anyway.
I obviously don't know about your life, so cannot say anything truly accurate about it. However, from what I see in your posts, I would say than your problem is not ineloquence, but fear of failure.
To be pithy: "If at first you don't succeed, try and try again."
And like I say above, try not to think of it as a procedure or algorithm. Perhaps try what I did: don't try to be an extrovert, but rather think of it as pretending to be one.
I must confess, I don't find your advice helpful either.
See HughRistik's great article and in particular this comment about how much of your own knowledge you can be unaware of if you've never been without it.
"Try, try again" is insufficient to improve. You can try forever without improvement if you can't recognize what you were doing right, and what you weren't. This information doesn't spontaneously unfold from your DNA as a result of being in social situations. And (see below), I have indeed tried again and again and again (edit: sentence wasn't completed in original comment).
I've already done exactly what you suggest, going out, and drinking, and benefitting form the lower inhibitions to talking that come with alcohol. I've done this quite a bit, but I've never seen any of the skill carry over to when I'm not intoxicated. Furthermore, I've pretended to be an extrovert, but it really makes no difference from the inside or on the outside: it doesn't automagically allow me to make conversation where I otherwise wouldn't.
Whatever problems I might have, fear of failure is not among them. It is, at most, fear of that failure cascading into very damaging personal consequences. And given my personal experience, these fears are extremely well-grounded. Nevertheless, I quite often go out to socialize and join groups, actively participate in them, and -- suprise surprise -- I do fail to form relationships or improve social skills, and I fail quite often, to the point where it's no longer a big deal.
I hate to be such a nannering nabob of negativity, but most of what I hear really is ignorant of the problems people like me might actually face, because the advice giver can't conceive of being in that state. I appreciate you trying to help, but, despite your claim to have been an introvert, you advice really sounds like you have not actually been in a position that's informative about this issue, as that would allow you to say more specifically what one has to do to cross the barrier.
I can teach people calculus and trigonometry. I can say a lot more than just, "try, don't be afraid of failure, and show some willpower". Why can't you?