A (long) guide to conversations

Crossposted from Reddit.

Epistemic status: highly likely

Warning: a few mentions of suicide and other heavy stuff near the end of (III).


Right. Let’s start with a detour.

Take two friends with lots of free time. Give one of them two large handkerchiefs and masking tape. He/she will be the interlocutor. Have him/her put you and your other friend in random faraway spots in a room where bumping into things won’t kill you, and have him/her blindfold you both and put tape over your mouths.

Done? Your task is to touch your right elbow with his left, and your left elbow with his right WITHOUT making any noise. If you don’t have friends nearby (or worse, no friends at all), then just play out the scenario in your head. Can you figure a way to find each other without cheating? Or how to orient your arms in the appropriate manner sans eyes and ears?

The point of this (thought) exercise is to show that interaction can happen without words. Most of us live as if our bodies are mere vessels for our brains, and my goal in this piece is to show that conversation, even online, is so much more than just words. But more importantly, I want to show that this surprisingly word-light activity is learnable and not just the exclusive domain of so-called extroverts.


Four years ago, I was the resident weird kid. I had no sense of boundaries: sometimes I’d borrow people’s stuff and only tell them afterwards. I interrupted people mid-sentence, and there were many times when I would lay down lengthy and complex arguments only to realise that the person I was talking to had already left.

In short, I had no social skills whatsoever and it was a miracle I survived until college without having been dunked into a trash bin.

Not to say I was blissfully unaware: I knew, and all those people you branded as weird probably knew too. And that is encouraging, because it tells us that all people (even people with mild autism or similar pathologies/disorders/[?] of similar magnitude) can learn social skills just by learning to listen and respond to that inbuilt social meter we all have. Of course, this is easier said that done, but we can make some headway by starting from the fundamentals and building up.

So! Interaction. As our little exercise demonstrates, interaction can happen without conversation. And often it happens even before you can actually converse. Take for instance what happens when a car suddenly overtakes you on the highway. To you, that might seem like a huge “Fuck you!” and if you happen on the same vehicle later on you will probably have a sudden surge of bad ideas. But consider the point of view of the driver. He (or she) may actually be an asswipe, or he might be rushing his wife to the hospital, or he might be late for work for the last time, or his Mexican garbanzo beans dinner might be minutes away from liberating itself, etc. It doesn’t matter. The point is, interactions depend on differences. The result of future interactions depends on how positive or negative your previous interactions were in total, with the most recent ones having the most weight. This is why first impressions matter (since at that moment it’s the only interaction contributing to the total) but can be overturned later, and why your clothes, your reputation, your posture, etc. all affect the flow and success of any conversation you will have with anyone.

If so, then we have a problem. Because this stuff is overwhelming! Nevermind specific conversational tricks, this crap is complex enough that you simply cannot be conscious of it while talking. This apparent difficulty has support from neuropsychology: people evolved to become cognitive misers, saving valuable nutrients by spending the least amount of brain cycles on problems, if at all. So we should take that as a clue that the road to social greatness is not to be found in reading self-help books (and long, rambling comments like this one) alone.

But if not, then where?


I have two exercises for you which come, of all places, from Scientology. The first is a variation of an activity called confronting:

Bribe a calm-mannered friend to keep you company for half a day. Give her a stopwatch, and pick two seats where you can be close enough to stare into each other’s eyes. Because you will: have her time your staring contest using the stopwatch so that, any blinking, looking away, laughter, bodily movement, etc. resets the timer. STRICTLY ENFORCE THIS RULE. The exercise ends once you have successfully maintained eye contact for an unbroken 20-minute duration.

(I actually did this with a friend once. Well, the exercise supposedly only cures one’s aversion to eye contact but it has the unfortunate side-effect of developing intimacy between two people. Use this knowledge at your own peril.)

The second exercise concerns speech fillers, but unfortunately the name escapes me at the moment. I’ll just call it enunciating. If you have problems with not being heard clearly, speaking too slow, getting talked over, etc. then this will help you address a small but essential part of those things.

Again, bribe a friend to help you here, but this time pick an assertive friend with a powerful voice. Stand 6-10 feet away from him in a room full of items and trinkets (say, in your average Pinoy home), and give him a pen and paper. His task is to tally your successes and point towards objects at random intervals. Your task is to immediately name the object he points to with the clearest, non-shouting voice you can muster. Tell him that any delay, mispronunciation, stutter, filler, softness, hesitation or (of course) mistake must not count towards your tally and that he has to shout at you, “Again!”. The exercise ends once you are able to maintain a 100-item-long streak.

Be warned however that this exercise is rather stressful so get yourself some ice cream and make sure you’re in the right headspace before and after you go through it.

Now, what do these two things have to do with conversations? As I’ve said before, you don’t need words to interact with other people, and even if you’ll eventually talk you’ve probably done a lot of wordless interaction already in what you wear and how you carry yourself. But these two basic skills: establishing eye contact and speaking clearly, will go a long way towards this pre-conversational part of the equation.

Okay, so your non-verbal prep is ready. The next step is to begin the conversation. But how do you approach someone out of the blue?

That’s the thing: whenever possible, do not approach someone “out of the blue”. The key to appearing naturalness is to always have an easily understood reason why you need to talk to someone. Maybe you just want to ask for directions. Maybe you need that red stapler from Liz and you have to scoot over four desks to get to her. Or heck, maybe you really just want to ask for her number. You don’t have to say it out loud: but having a justification planted in your head, however doubtful, is an excellent way to avoid awkwardness on your part1.

Now, suppose you have your justification and it’s not an immediately practical one. You wanna get to know her, great! But how do you do that without the dreaded awkward silence? For this, we need another tool in our toolkit: the close-ended vs open-ended distinction.

People usually trip over this a lot. They think conversation involves asking hundreds of small questions, hoping that something will stick. And they’re right: your persona as her unwanted job interviewer will stick and you’ll be relegated to the fair-weather friendzone as you both contemplate the passing of seconds with each cricket chirp.

The thing you need is to distinguish close-ended questions and open-ended ones. Close-ended questions are questions like: “What’s your name?”, “Where are you from?”, and “How much is 20 grams? Now don’t cheat me here…”. They are not inherently bad. In fact, the ‘small’ in small talk comes from it being entirely composed of close-ended questions. You are always ‘closing the topic’ by requesting direct, one-word or one-sentence answers, but of course it’s the only way to get that kind of info sometimes.

(I remember this joke about a groom thinking to himself: “So that’s what her first name is!” while the priest was reading his and his soon-to-be-wife’s wedding vows. Small talk is small, but even the small things are sometimes essential.)

Open-ended questions on the other hand are questions of “why?” and “how?”. They are useful to ask because you get to know the other person’s beliefs and ways of thinking. For many people, this is the whole point of having conversations in the first place. But too many open-ended questions at once will burn off conversational energy very quickly. People need space to think, and you have to allow them this space or you’ll end up as the guy who started asking about her mother’s parenting style 15 seconds before she gets off at the next bus stop.

I’d like to talk about this notion of ‘space’ more because it’s really important. You give people space by closing the topic or by being silent. Silence is usually treated as a failure of communication but it shouldn’t be. Silence is useful. When I was in high school, I used to feel out my relationships with other people depending on how long we can keep silent comfortably. And even more interestingly, you can use silence to get people to divulge information. As I said, people aren’t comfortable with ill-timed silence and so they will try to fill it whenever possible. Try slipping in conversation a potentially sensitive question like “What turns you on?” and then stop. If he or she doesn’t rebuke you immediately (in which case, abort!) and instead tries to hedge a vague or indirect answer, just keep staring. He or she will eventually laugh and expound. Trust me, this stuff I learned unconsciously and once it was pointed out to me, I’ve never had it fail. Das ist die Dunklen Künste. Use sparingly.

So what do we have so far? A conversation need not be 24/7 yakking and sometimes you just need to shut up. This flows nicely into our next tool, because you need to shut up in order to listen.

People love talking about themselves. And those bastards who claim otherwise? They usually have some other interest like cars or other-people gossip they can drone on and on about indefinitely. And so to be a good conversationalist is to be a good listener.

The catch? Well, there are two:

  1. We don’t really know how to listen.

  2. We overestimate how much listening we actually do.

Lemme take care of this point off the bat: listening is not standing there, trying to look interested while waiting for your turn to speak. This is far too common a failure mode and is why you find people saying “You can do it!” after hearing someone exclaim surrender2 3.

But if that’s not listening, then what is? I claim that listening is digesting their words on their terms. It’s okay to take a few moments: after all, very few people can claim stoicism after hearing about a suicide attempt. But you have to collect yourself and respond to each point. If you’re dealing with a heavy topic, this is not the time for you to get overwhelmed by your own feelings (which makes sense, because, well, you ARE trying to support the person)4. In particular, you have to focus on how they’re feeling first and offer advice second, if at all.

Actually, some people highlight a sex-related difference5 for this point. People say men (and genders of the same behavioural cluster) prefer advice over discussing feelings, while women (and cluster) prefer the opposite. In my experience, the more relevant axis is Simon Baron-Cohen’s systematisers vs empathisers6, with the former preferring advice over feelings and the latter preferring feelings over advice.

Right, so we have a better idea now of how to listen, but again we have to be careful: we still tend to overestimate the amount of listening we actually do. Ideally, a conversation between two people is 50% speaking, 50% listening on both sides. My rule of thumb here is this:

When you feel you’ve only talked 20% of the time, then you actually talked 50% of the time.

I call it the 20-is-50 rule. If you’re dealing with a heavy topic, then you actually have to speak only 20% of the time. So better to let your spit rot than to spit advice needlessly.


Wow, okay, I’m almost at 3500 words and we still have loads to discuss. In particular, since we’re done with the how (and TL;DR readers can stop here), let’s delve into the why.

Whither conversation? Whither talking? Why do we bother interacting with people in the first place?

I think we can only really understand conversation within the context of trust and intimacy. Keep in mind they are not the same things. Take for example two friends who have known each other for 20 years. They might trust each other with their lives, and yet might never have been physically nor emotionally intimate with each other7. Some level of intimacy is necessary for trust—after all, you wouldn’t normally entrust your newborn to a random stranger you’ve never even talked to—but it is not a sufficient condition.

Nevertheless, they are but different facets of the same underlying theme: human relationships. Quite frankly, it’s actually pretty hard to model us humans—I’d dare say even harder than modeling particles! The best we can do is to simplify and look at things from a high enough level that things start to make sense in relationships we can understand8.

So what is trust? I’d say it’s the thing we use to validate exchanges. Heck, money started off as this. People found it difficult to keep gold in their houses, so they entrusted their nuggets to the local blacksmith (who could then hire more guards and put in more safety measures). This was the start of banking. Eventually, more people deposited their money in these proto-banks so the blacksmiths had to give out receipts to keep track of whose gold is whose.

Now, as people became richer and their transactions bigger, more and more of these metals had to be transported in between banks (and in between individuals). This exposed the trade to a lot of risk from bandits (and dishonest mercenaries). Eventually, people thought, “Heck, why don’t I just give my receipts to you so you can get my gold from Blacksmith X without all this hassle?” and voila, paper money!

So money then was invented on the basis of trust. You have to put trust in the blacksmith, in the validity of his receipts, in the improbability of your business partner forging the receipts, in the guards defending the gold vaults, and the engineers who designed the security protocols. This web of trust-based exchange expands as the web of human relationships expands, and the same is true even if the exchange is not in terms of money but in terms of information.

Conversations then, thought purely as information exchange, must involve trust in a similar way.

But of course, we know that conversations are not just information exchanges. We like talking. We like talking for talking’s sake. We get closer to people the more we talk to them. So conversations are not zero-sum exchanges: they can actually produce value to us. This then is my view: conversations, more than anything else, are producers of intimacy.

A fun way to restate this is in the form of a game:

How much intimacy can I mine from this conversation while spending the least amount of information?

Viewed in this way, you can see why people get miffed when someone’s doing the 100 Questions routine on them, or when they notice that in the last three hours you’ve spent conversing, they haven’t really learned anything substantial about you.

And because this is a game, there’s a way to win. :)

Conversations can lead to intimacy spirals, or the process by which intimacy breaks down people’s barriers and lets you do things like hold hands or ask about a pet’s passing. There are two things of interest here:

1. Intimacy spirals have no limit.

I can personally attest to this. I met my bestfriend rather late in college, but we hit it off pretty well. So well, in fact, that I can literally talk to her about anything. Even feeding zombie guts to babies, or the taste of her…um yeah, so this is getting into very personal territory, but believe me when I say that I literally did not think that level of closeness was possible. We literally never had to ask each other’s whereabouts, because we’d just know.

(Yeah, if you’re interested in this story, PM me hahahahaha)

2. Intimacy spirals can proceed as fast you like.

This is why people can “hit it off with a stranger in Europe” in two days. Not inviting people to test this, but personally I can get pretty far into a new intimacy spiral in the span of an hour.

Speaking of which, there some people, maybe 10-15% of the population, who have this tendency to defuse intimacy spirals with sarcasm or humour. This usually (but not always) implies some sort of underlying reason for the defensiveness and reluctance to trust strangers. I’ve never really managed to figure out how to get past these walls (quite frankly because I’m still learning), but in some select cases, a few bottles of beer at 1 AM can help9.


Hmm, what else? Group convos?

Group conversations are a different beast. You can only sustain a conversation with four people or fewer. A five-man conversation is a two-man + three-man convo, or a four-man conversation with one person staying quiet. It may oscillate between these two stable states, but bigger convocules are always unstable.

In any case, once you have the foundations, the game becomes how many people you can practice with. Volume is so much more important than quality that I’ll say it again. Volume is so much more important than quality. I can attribute my success in this regard to the 200+ people I met when I joined an org in college. In my uni, at least, the org culture is centered on obtaining signatures from members, and my org in particular requires its applicants to arrange a short interview with each and every member, plus any reasonable requirement that he or she may require of the app. (Yes, it’s as daunting as it sounds.)

In my case, my only requirement was that we talk for at least an hour. And I kept it up for over three years, thereby allowing myself a tight feedback loop with respect to which I can improve my conversation skills (and of course make friends along the way).

That is Takeaway #1: loop yourself into a tight feedback loop.

That could take the form of going to co-worker lunch-outs, talking to Redditors online, or heck, even just hanging out at the watercooler area in your faculty or office. The point is that you will not improve your social skills by reading alone: you actually have to go out there and practice. Hence the exercises. Hence the format of this piece. And hence, my insistence on going out there to practice.

But of course, telling people to practice is as useful as telling people to “draw the rest of the fucking owl”. There are many ways to practice. You could do it the Bruce Lee way: adopt one style of conversation and do it 10 000 times. You could do it the scientific way: make a hypothesis, test it out in the field, and analyse the results. I propose doing it the monkey-brain way: imitate other people and trust that you’ll get it.

This is Takeaway #2: trust your monkey-brain.

This monkey-brain business isn’t as stupid as it sounds. After all, you unconsciously picked up walking, biking, and picking locks without being explicitly told to do so—okay, maybe not the picking locks part, but the part of your mind that’s used to words is just a really small part of the thinking you do everyday10.

A useful exercise to get your monkey-brain running is to tune out the actual words people are using and observe their nonverbal cues. Can you figure out where they are in their intimacy spiral just from their tone, volume, and body language?

…I’ll stop here, because if you let me ramble on I’ll go over 5000 words. But I hope you learn something from all this. At least, I did, trying to condense three years worth of enjoyable (and sometimes heart-wrenching) experiences in a self-help tutorial.

If you have any questions, feel free to PM me. I’ll be the first to say that I’m not yet an expert on these things (mostly because I’ve seen what actual social experts can do), but if I leave you with something new, then that’s one more person, one more universe, I can possibly get to know.

  1. And this is true even online. That’s why it’s so much easier to PM your crushie if you have to borrow notes anyway. It’s free plausible deniability on your part (because after all, you’re just asking for notes) and it also makes the entire interaction more palatable on her part (and if you’re lucky, downright delightful — but more on this later). 
  2. Okay, that was an exaggeration. Some people just don’t know what to say, and unfortunately for their confiding friends it doesn’t really help all that much and might even make them feel unlistened to. I hope this piece can alleviate that problem somewhat. And if not, well, you can confide in me
  3. Actually I think you can understand this in terms of silence. After an emotionally heavy story, people are usually rendered speechless. But when your friend has just finished hers and is inconsolably weeping two feet away, you are pressed for a response in order not to appear rude or awkward. So you speak, and this is usually the only cliché that comes to mind. 
  4. This is also not the time to share your own story, even if it’s relevant to his case. Again, you are trying to LISTEN here. The other person always comes first. 
  5. Another interesting sex-related difference is that women tend to get talked over much more than men and their opinions maliciously credit-grabbed at a later time. You don’t need to subscribe to feminism to accept these facts. Use them as you will. 
  6. Yes, I am aware of criticisms of Baron-Cohen’s research. But I’m a Bayesian so I’ll use the model anyway. 
  7. And for internet friends, they might not have even seen each other yet IRL! 
  8. This isn’t to say that we can never understand humans on a mathematical level. Confusion exists in the map, not the territory. Your inability to write down a ‘human equation’ does not have any bearing whatsoever on our “modelability” (after all, you CAN brute force a mathematical model of a human by simulating all our 10^27 atoms in a planet-sized computer). We need better models, not a surrender to “the unfathomable mystery of the universe”. 
  9. Oh yes, drinking is cheating. People do let their guards down when you give them alcohol (as long as you get shitfaced as well). Use sparingly, or like me your liver will suffer. 
  10. And for those without a mind’s voice, good luck. I don’t think many of my techniques will be of much help to you, but you would still derive a lot of benefit from Takeaway #1. It’s just that you’ll be using a different sort of thinking (something closer to symbolic pattern recognition) to process all this stuff and I just can’t help you there. 

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