One of the things that makes Michael Vassar an interesting person to be around is that he has an opinion about everything. If you locked him up in an empty room with grey walls, it would probably take the man about thirty seconds before he'd start analyzing the historical influence of the Enlightenment on the tradition of locking people up in empty rooms with grey walls.
Likewise, in the recent LW meetup, I noticed that I was naturally drawn to the people who most easily ended up talking about interesting things. I spent a while just listening to HughRistik's theories on the differences between men and women, for instance. There were a few occasions when I engaged in some small talk with new people, but not all of them took very long, as I failed to lead the conversation into territory where one of us would have plenty of opinions.
I have two major deficiencies in trying to mimic this behavior. One, I'm by nature more of a listener than speaker. I usually prefer to let other people talk so that I can just soak up the information being offered. Second, my native way of thought is closer to text than speech. At best, I can generate thoughts as fast as I can type. But in speech, I often have difficulty formulating my thoughts into coherent sentences fast enough and frequently hesitate.
Both of these problems are solvable by having a sufficiently well built-up storage of cached thoughts that I don't need to generate everything in real time. On the occasions when a conversations happens to drift into a topic I'm sufficiently familiar with, I'm often able to overcome the limitations and contribute meaningfully to the discussion. This implies two things. First, that I need to generate cached thoughts in more subjects than I currently have. Seconds, that I need an ability to more reliably steer conversation into subjects that I actually do have cached thoughts about.
Below is a preliminary "conversational map" I generated as an exercise. The top three subjects - the weather, the other person's background (job and education), people's hobbies - are classical small talk subjects. Below them are a bunch of subjects that I feel like I can spend at least a while talking about, and possible paths leading from one subject to another. My goal in generating the map is to create a huge web of interesting subjects, so that I can use the small talk openings to bootstrap the conversation into basically anything I happen to be interested in.

This map is still pretty small, but it can be expanded to an arbitrary degree. (This is also one of the times when I wish my netbook had a bigger screen.) I thought that I didn't have very many things that I could easily talk with people about, but once I started explicitly brainstorming for them, I realized that there were a lot of those.
My intention is to spend a while generating conversational charts like this and then spend some time fleshing out the actual transitions between subjects. The benefit from this process should be two-fold. Practice in creating transitions between subjects will make it easier to generate such transitions in real time conversations. And if I can't actually come up with anything in real time, I can fall back to the cache of transitions and subjects that I've built up.
Naturally, the process needs to be guided by what the other person shows an interest in. If they show no interest in some subject I mention, it's time to move the topic to another cluster. Many of the subjects in this chart are also pretty inflammable: there are environments where pretty much everything in the politics cluster should probably be kept off-limits, for instance. Exercise your common sense when building and using your own conversational charts.
(Thanks to Justin Shovelain for mentioning that Michael Vassar seems to have a big huge conversational web that all his discussions take place in. That notion was one of the original sources for this idea.)
As you may have gathered from previous interactions with me and others here, I'm generally careful about my phrasing when I do give advice: I normally preface it with "Here is what I recommend" or the like. I wasn't giving you advice yet, but collecting information prior to giving advice.
I asked about Improv because it points out one specific thing I think you're doing wrong: you're often "blocking" as the improv jargon calls it. I would recommend you learn about (and practice) "yes and".
Your answer to my question is "blocking" in a synctactically typical manner: "yes to the second, but I lost brain cells going to the first meeting". "Yes, but" when what you're looking for in conversation is "yes, and". You're telling me in an oblique way ("lost brain cells") that Toastmasters wasn't a satisfactory experience for you, without giving me an opening for further conversation on that topic.
You could have phrased that in a thousand other ways more inviting of further conversation. Example: "Yes, I did try Toastmasters, and I was bored out of my mind; why did you ask, and what were you thinking I should have expected to get out of attending?"
I disagree with your assessment that "the problems is not being in groups per se". You've had many people here tell you that they find interacting with you often unpleasant, even though they are by no means "random people", they are from a social set that you have chosen and that by your own admission you want to get more closely involved with.
And to repeat something I've said previously: people discussing this topic with you here and now may not be very good advice-givers, but then you're not necessarily a very good advice-taker. Eye, mote, beam.
I've upvoted your response to the Go analogy because it's factually true. One thing you're overlooking, though, is that when a Go novice asks a Go master what they should learn about, it's a good idea to try very hard to extract something from the master's advice, no matter how bad the master seems to be at explaining. Otherwise you risk entering a common failure mode related to "blocking":
If you're fed up with one master, go seek another - rather than fruitlessly spend energy blocking the one. But if many masters are telling you the same thing, perhaps it's time to update.
Yikes! I think you're overextrapolating what I was trying to do based on my use or nonuse of various codewords that you've decreed to have certain meanings. I said "yes but" because I wasn't trying to invite conversation as I would in an in-person discussion, so it's no surprise that the remark doesn't leave you optio... (read more)