This was written on March 25th, 2014.

I like good conversations. I think good conversations are enriching, good for the mind and soul. Ideally I’d like to be having good conversations with everybody I meet. Everybody should be having good conversations with everybody all the time. Life is too short, no?

Unfortunately good conversations aren’t the norm, not for everyone. A lot of people sympathise with the idea that small talk sucks. I saw a thread on r/offmychest where lots of people sympathised with the OP, who was frustrated with small talk.

Small talk by itself isn’t inherently a bad thing. It serves a function. But I think people do have a need to go beyond small talk, and that doesn’t happen nearly as often as many of us would like.

People you can’t really talk to:

A litmus test: I realize that I have friends (and even family) that I ‘can’t really talk to’. What does that mean, why is that so? I don’t think it’s as simple as “some people want deep conversations about life and philosophy and not everybody can provide that”. I think that’s reductive and unhelpful. And I think “deep conversations about life” can sometimes be boring and unfulfilling.

But it’s also true that some people are just easier to talk to. Why is that?

I have a couple of vague theories I’d like to expound and explore.

Consider the following situation: you’re having a conversation with someone, and you’re both talking about something neither of you is particularly interested in. How does the conversation develop? How do you go from boring stuff neither of us is interested in to talking about stuff where both of us can be interesting and useful to another?

Asking the right questions

I think a big part of it is about asking the right questions. For most of my life- even now, I have to admit- I tend to dominate conversations by talking over everybody. I attribute this partially to growing up in an environment where everyone talked over everyone, so it was the only way to be heard. The most interesting topic takes precedence. I expected people to interrupt me if I m getting boring, or if they have something more important or useful to say. I’ve since realised that not everybody shares this perspective. Some people are used to politely waiting for their turn to speak, and if someone else is talking all over them, then their valuable insights and perspectives go wasted, unheard.

I talk a lot because I try to be useful to others. I hope that something I have on my mind or in my ‘archives’ might be the piece of information that someone needs to get themselves unstuck. But I realize that this won’t always be interpreted that way. I didn’t realize that it makes me look selfish, self-obsessed.

A more enlightened person would know to ask questions instead. People are always hungry to be asked good questions. People who are silent don’t always want to be talked at; sometimes they want to be asked a good question.

Questions > Statements

A question is almost always superior to a statement. Even if you’re a selfish person who doesn’t care about others, knowing what others are thinking is a fabulous way to get information necessary to further your agenda.

I didn’t realize this when I was younger. I revealed secrets and frustrations and all sorts of things that got me in trouble because I trusted that people would interpret information the way I did. Now I know better. If somebody tells you a secret, you keep it, no matter how many brownie points you’d get for sharing it with seemingly well-meaning others. Having a reputation for keeping secrets puts you in a position to become a repository of information with immense strategic value.

I don’t mean that in a conniving, cruel sense. Knowing what a group of friends thinks about each other and/or a particular situation by gently probing with your benevolent curiosity equips you to resolve conflicts in an amiable, healthy way. You could also pit people against each other for your amusement and profit, like the villain from Mean Girls.

Information-gathering for good:

In fact, if you want to diffuse the negative effects of such villainy, you’re going to have to do the same information gathering yourself. Knowledge is power, and that power can be used in any way that the wielder sees fit. If the sensible abstain (think Benjamin from Animal Farm, the old donkey who’d seen it all before and wasn’t interested in getting involved), then the malicious prevail. All that’s needed for evil to triumph is for good people to do nothing.

I think it’s important to be respectful towards others, even people who might be ‘lesser’ than you by some measure or another. I used to mock and laugh at people who were ‘stupid’ or unattractive or socially inept or otherwise incompetent I some way. It’s easy to do it because these are easy targets. By mocking them you communicate your superiority, both to yourself and to others.

But this is toxic, dangerous behaviour. Once you start mocking others because you’re somehow ‘better’ than them, you put yourself on the battlefield of conditional esteem. And you can’t win. You can’t run forever. You’re better because you’re smarter? Someone’s always smarter than you, fitter, richer, better looking. So never mock others. The enemy is ignorance, not people who are ignorant. Hatred, not people who are hateful (see Westboro Church). Be thoughtful, gracious, kind, compassionate and forgiving- not just because they are nice sounding ideals, but because they’re literally good for you.

What do you laugh at?

But if you don’t laugh at the weak, or weakness, who do you laugh at? Should life be devoid of humor? Of course not. That’s incredibly depressing. Life is pretty absurd. There’s a lot to laugh at. Our own ignorance is an incredible, endless source of powerful punchlines. We should laugh at ourselves, our own mistakes, our foibles. I’ve come to believe that comedy should serve to protect the weak and downtrodden, and mock oppression. It should reveal the absurdity of racism and sexism and help people breathe and live easier, rather than in fear of arbitrary judgement from the privileged.

People of course will always have politically incorrect thoughts. I think it’s important to try and create an environment where they can air them and be informed about their ignorance. I saw a quote on Tumblr about how people with privileged are often shocked and outraged when victims of structural oppression and microaggressions call them out, and how victims are never given a nice, pleasant introduction to sexism or racism. I’m thrown into a racist world the day I’m born, so why should I give racists an easy time?

Desired end-state

I think it boils down to desired end-state. What is the outcome you want to achieve, and what’s the best way to achieve it? If being nice to oppressors yields a superior conversion rate than being snide, sarcastic or hostile, then I’m committed to being nice. Of course I completely understand if people don’t want to be nice to their oppressors. Different people have different desired end-states and different ideas about how those end-states might be reached.

Thoughtfulness

What distinguishes a person I enjoy talking to from a person I don’t? I think thoughtfulness. I much prefer the term thoughtfulness to intelligence, because the term “intelligent” is incredibly loaded. A person can be intelligent and a bigot, intelligent and really rude and ignorant or socially inept. I think thoughtfulness is a much superior ‘measure’ of a person (if people had to be measured, for the purpose of some form of social decisionmaking).

I think there is some correlation between deep reading and thoughtfulness. If a person tells me that they’ve read a certain book and can describe to me why they like it, I think I can have a better than random estimation about a person’s ‘smartness’ or thoughtfulness if I know how much they’ve read. Specifically, how much they’ve willingly read for their own pleasure and enjoyment.