If your goal is conversational acuity, I'd suggest narrowing your focus to trivia about people, and about the categories that they are likely to use about themselves. I got this trick from a guy who worked at a hotel desk night shift for a year or two, and spent the time training up his skill at conversations with strangers.
Step 1: During the standard greeting protocol, think about the ways in which the person you are talking to might self-identify. Are they in uniform? Does context provide you any clues? Usually you can ask about this directly in polite ways- "So, what brings you here?", etc. You are looking for identity groups- professions, hobbies, communities. Identities related to race and gender are best avoided for first meetings, so discard those.
Step 2: Make a comment that affirms their identity directly and pleasantly. This is where the trivia comes in handy. If the person is on a football team, compliment them on some specific event that showed off the team's skill. If they are a medical professional, you might comment about a new hospital that was recently constructed in your neighborhood (thus implying that their profession is successful). Jokes are fine, as long as they are lighthearted and demonstrate a degree of 'insider knowledge'. But the key here is that unusual and insightful observations about people's identities will typically garner a disproportionately positive response, as long as the tone stays affirming- knowing a lot of rare trivia about these identities can be enormously helpful during this step.
Step 3: Shut up and ask questions. Once you have identified and affirmed a specific aspect of somebody's identity, you can start with the seeds of what you do know, and use that as a basis for open-ended questions. Since you have demonstrated solidarity with their 'team', at this point most people will be more than willing to answer such questions in depth. The conversation can then continue for an arbitrarily long period of time (with the other person supplying most of the information), and as a bonus you will pick up more trivia and generally improve your understanding of society. If you continue to make observations about their identity during this time, and use those observations to ask further questions, people will usually think of you as intelligent.
There are some relevant suggestions in Leil Lowndes's book How to Talk to Anyone:
[W]hen you crave a bigger hit of insider lingo, start reading trade journals. Those are the closed-circulation magazines that go to members of various industries. Ask your friends in different jobs to lend you one so you’ll have even more fuel for the conversational fire.
All industries have one or two. You’ll see big glossy rags with names like Automotive News, Restaurant Business, Pool and SpaNews, Trucking Industry, and even Hogs Today for people in the pig business. (Excuse me, they call themselves “swine practitioners.” Hey, you never know when, to make your next big sale, it will help to speak pig.) Any one issue will give you a sample of their lingo and inform you of the hottest issues in that field.
When it comes to people’s hobbies and interests, browse through magazines on running, working out, bicycling, skiing, swimming, and surfing. Large magazine stores carry biker rags, boxer rags, bowler rags, even bull-riding rags. You’ll find thousands of special-interest magazines published every month.
She also suggests trying out new activities yourself, just for the sake of learning more about them:
Once a month, scramble your life. Do something you’d never dream of doing. Participate in a sport, go to an exhibition, hear a lecture on something totally out of your experience. You get 80 percent of the right lingo and insider questions from just one exposure.
(cf. Eliezer's "A New Day")
Regarding people: I always thought reading an anthropology book for anecdotes about obscure tribes would make great party fodder. Especially their sexual/romantic norms (depending on the party).
Be wary of telling trivia if you aren't otherwise grounded in a subject. In a smart crowd, chances are someone will understand the subject better than you do. If you attempt to "enlighten" a more knowledgeable person and you get it wrong, they may quietly dismiss you and everything else you have to say.
To signal smart to a smart person, ask them questions about progressively more arcane parts of their field.
How did you decide against using Anki / spaced repetition? To me it seems like a trivially obvious choice if your goal is to actually memorize a bunch of small facts.
Anki makes it easy to memorize facts, but not necessarily to bring them to mind unless you're explicitly searching for them.
I added the date of the first moon landing to my Anki deck with the intention of tweeting about it on the anniversary, and if you asked me when it was I could have told you: July 20th, 1969. But yesterday came and went, and I totally forgot. (Fortunately, I also remember that the first moonwalk was the day after the landing.)
Anki makes it easy to memorize facts, but not necessarily to bring them to mind unless you're explicitly searching for them.
Which sounds useful for trivia. For example, I found Mnemosyne helpful studying for Quizbowl.
Do you believe that Anki is worse in that regard than some other approach? I feel like Anki is far from perfect, but basically a strict improvement over just reading and occasionally re-reading stuff.
In other words, I interpret your criticism as "there must be a better system out there, waiting for someone to find", not as "don't use Anki".
Yeah, I did do a bit of review (reading back through my notes), but I kind of fell out of that habit because I became too busy. I never got round to trying to implement a spaced repetition system because higher priorities took over.
I would suggest that if your desired metric is anything remotely like "total number of trivia facts I can recall easily from a suitable prompt", then making Anki cards is obviously a better use of your time than reading more new articles. And extremely superior to making your own spaced repetition system. (That might change once you've used Anki enough to have identified shortcomings. But don't let daydreams of perfect systems prevent you from moving from a bad system to a good one.)
If anyone has already posted any similar posts, then I would really appreciate any links.
Off the top of my head, Swimmer963 wrote about her experiences trying meditation, and I wrote about trying to notice confusion better. Gwern has run more serious self-experiments, and he talks about a bunch of them in the context of value of information here.
There might be a trainable skill of noticing high-leverage facts. For example, a friend of mine claims that a modest weekly investment in keeping up with soccer allows him to 'have a good conversation with any man'. In particular example, a basic knowledge of the proceedings of a FIFA World Cup while it is taking place is extremely cheap but might be extremely high leverage depending on where one lives and the demographic distribution of one's interlocutors.
Similarly 'current affairs' (legislation, policy, political manoeuvrings, disasters, humorous stories, etc.)
Also, I encourage this kind of experimentation post.
Good listeners are remembered as good conversationalist. A little bit of "oh really? tell me about that" goes a long way.
There has been some talk of a lack of content being posted to Less Wrong, so I decided to start a series on various experiments that I've tried and what I've learned from them as I believe that experimentation is key to being a rationalist. My first few posts will be adapted from content I've written for /r/socialskills, but as Less Wrong has a broader scope I plan to post some original content too. I hope that this post will encourage other people to share detailed descriptions of the experiments that they have tried as I believe that this is much more valuable than a list of lessons posted outside of the context in which they were learned. If anyone has already posted any similar posts, then I would really appreciate any links.
Trivia Experiment
I used to have a lot of trouble in conversation thinking of things to say. I wanted to be a more interesting person and I noticed that my brother uses his knowledge of a broad range of topics to engage people in conversations, so I wanted to do the same.
I was drawn quite quickly towards facts because of how quickly they can be read. If a piece of trivia takes 10 seconds to read, then you can read 360 in an hour. If only 5% are good, then that's still 18 usable facts per hour. Articles are longer, but have significantly higher chances of teaching you something. It seemed like you should be able to prevent ever running out of things to talk about with a reasonable investment of time. It didn't quite work out this way, but this was the idea.d
Another motivation was that I have always valued intelligence and learning more information made me feel good about myself.
Sources
Today I learned: #1 recommended source
The straight dope: Many articles in the archive are quite interesting, but I unsubscribed because I found the more recent ones boring
Cracked: Not the most reliable source and can be a huge time sink, but occasionally there are articles there that will give you 6 or 7 interesting facts in one go
Dr Karl: Science blog
I read through the top 1000 links on Today I learned, the entire archive of the straight dope, maybe half of damn interesting and now I know, half of Karl and all the mythbusters results up to about a year or two ago. We are pretty much talking about months of solid reading.
Results
You probably guessed it, but my return on investment wasn't actually that great. I tended to consume this trivia in ridiculously huge batches because by reading all this information I at least felt like I was doing something. If someone came up to me and asked me for a random piece of trivia - I actually don't have that much that I can pull out. It's actually much easier if someone asks about a specific topic, but there's still not that much I can access.
To test my knowledge I decided to pick the first three topics that came into my head and see how much random trivia I could remember about each. As you can see, the results were rather disappointing:
Cats:
Dogs:
Rats/mice:
Knowing these facts does occasionally help me by giving me something interesting to say when I wouldn't have otherwise had it, but quite often I want to quote one of these facts, but I can't quite remember the details. It's hard to quantify how much this helps me though. There have been a few times when I've been able to get someone interested in a conversation that they wouldn't have otherwise been interested in, but I can also go a dozen conversations without quoting any of these facts. No-one has ever gone "Wow, you know so many facts!". Another motivation I had was that being knowledgeable makes me feel good about myself. I don't believe that there was any significant impact in this regard either - I don't have a strong self-concept of myself as someone who is particularly knowledgeable about random facts. Overall this experiment was quite disappointing given the high time investment.
Other benefits:
While the social benefits have been extremely minimal, learning all of these facts has expanded my world view.
Possible Refinements:
While this technique worked poorly for me, there are many changes that I could have made that might have improved effectiveness.
I believe that if I had spread my reading out over a greater period of time, then the cost would have been justified. Part of this would have been improved retention and part of this would have been having a new interesting fact to use in conversation every week that I know I hadn't told anyone else before.
The social benefits are rather minimal, so it would be difficult to get them to match up with the time invested. I believe that with enough refinement, someone could improve their effectiveness to the stage where the benefits matched up with the effort invested, but broadening one's knowledge will always be the primary advantage gained.