For some people, meeting others and making conversation happen regularly without the need for supplementary effort or thought. This article is not for them. It is for those of us who, for any of a plethora of reasons, do not brush as smoothly or magnetically against their fellow human beings in passing.
Of course, the surest way to fail in this regard is to neglect the in passing bit. If you stop to think about it, other people are the most incredible aspect of the drama we live in. To ignore them—to hide from them literally or figuratively—is to starve for a unique beauty. The Dictionary of Obscure Sorrows has a word which pertains to this, sonder: “the realization that each random passerby is living a life as vivid and complex as your own—populated with their own ambitions, friends, routines, worries and inherited craziness—an epic story that continues invisibly around you like an anthill sprawling deep underground, with elaborate passageways to thousands of other lives that you’ll never know existed, in which you might appear only once, as an extra sipping coffee in the background, as a blur of traffic passing on the highway, as a lighted window at dusk.” Perhaps the difficulty in reaching out and engaging with others is due to this very phenomenon. We are humbled by sonder, consciously or subconsciously, and flee in awe of a complexity which daunts us from within and outright blinds us from without.
Half of the equation is in meeting people. There is room for entire novels describing various outlets and situations which offer good opportunities for meeting people. But that is an easily Google-able topic. To offer a mere tip of the iceberg, I would suggest a focus on situations which prompt symbiosis, or reliance on others for a common goal. So, rather than just going to a coffee shop and striking up a conversation with a stranger (which is a perfectly fine thing to do, by the way), you will have better odds at finding chemistry in situations where there exists an abstract thing that you and person X are both there for, especially if you and person X can cooperate towards said abstraction. Examples of this situation include book clubs, painting classes and recreational sports leagues.
The more interesting half to this equation is in the moments, minutes and hours which follow meeting a person: the art of conversation. The intimate unveiling, the second most effective portal to connect one brain’s dance to another (the first being physical expression…although less understood. Most people make vague judgements of others as a result of it without really knowing why).
Brian Christian, upon being invited to partake as a human participant in the annual Turing Test (a competition wherein artificial intelligence programs and humans have textual conversations with judges, and the judges try and guess which is a program), decided to investigate conversation to increase his chances of being identified as human. In his fascinating book about the experience, The Most Human Human, he reveals the ways in which humans interact that are not yet mimicked by simple algorithms. Among the more important points, he distinguishes between form and content: “Having a sense of a person—their disposition, character, ‘way of being in the world’—and knowing about them—where they grew up, how many siblings they have, what they majored in, where they work—are two rather different things.” We tend to focus too much on content (like programs). And while content can be revealing, often a launching pad for further conversation, it is the amorphous form which leaves us with a vague, almost emotional impression of a person. Have you ever thought, after meeting someone briefly, I really liked ____, or, something about ____ annoyed me? That’s their form. Try simply bantering and avoid the typical conversational benchmarks. It will be awkward at first, but the practice is worth the product.
Be wary of advice that calls for formulaic technique in conversation. Common examples are: “avoid talking about religion or politics,” and “listen more than you talk.” In my experience, both of these suggestions are usually sound. Usually–People are too complex to fit neatly in a formula; site-specificity is key. A good conversationalist tailors their words to the audience, the reactions they get, the time they have, the setting. They are perceptive and respect the input. If the person you’re talking with seems shy but interested, talking more than listening is appropriate.
Use the setting to your advantage. Nearly all conversations with strangers begin “in-book” or “scripted.” They start with remarks about the setting (“That test was brutal!” or “What did you think of ___?”). What follows is almost predictable. And then sometimes “it” happens—they will break from the script and riff back and forth until they end up talking about UFOs or something else entirely unrelated but totally revealing of the person, their form. Starting is the hardest part. If you break from script, you will be in a good place: a fun, evanescent, unconsidered calisthenic of two minds. To get there, you need to make contact, express interest and then ride the waves with a limber mind. It is difficult to do this if you’re encumbered with all sorts of templates-to-conversation that you read about.
Don’t approach conversation as an activity with an objective. Don’t strive for any single outcome (“I want to make them laugh as much as possible” or “I want them to have this impression of me”). Approach it as you would a sandbox, and just make something cool. You have nothing to prove and there is no score. Give yourself this freedom and you might find that conversing well—that is, enjoyably—is easy and natural. We are hardwired to be social. Far more important than having a “plan,” or something you recited in your head a dozen times, is being in a good conversational state. A good state is one including a cool head and genuine enthusiasm. If you’re nervous or over-analytical, it will be difficult to foster real interest in the conversation, and you will never break from the script.
Some basic strategies to conversation which can exist within the above (non?)framework: leave “hooks” on the end of your statements or clauses. Instead of answering a question straightly and succinctly, try and lead the answer into something else if you know it will otherwise be a dead-end. Include anecdotes, be overly specific (answer “what have you been up to?” not with “I was reading,” but with what you were reading, for example), and pose questions in interesting ways (like statements: “you seem like you would enjoy ____’s music,” or “what do you do when you’re not ____? (insert situation)”). Also, answer questions “porously,” as Christian puts it. Answer in such a way that the other may jump in when they wish. Read their face and body (site-specificity) to determine if they are really interested in what you’re saying, and give them the opportunity to cut in or change direction.
As you might have gleaned, conversation is more about being uninhibited than it is about following rules. Your form will fit with that of some people, and it will conflict with some. But this is not a win/lose scenario. Getting to know people, regardless of outcomes, is an enriching experience.