3 Tips on the Art of Conversation

3 Tips on the Art of Conversation

~ 3 personalized tips on the “art” of conversation.

I remember reading How to Win Friends and Influence People (1936), the classic self-help book, in high school. I recall the lessons less and more how it made me feel. Dale Carnegie’s early 20th-century mind’s communicae, with its systematized strategy for making people like you, respect you, be amenable to influence from you… kinda made me feel like a sociopath.

Don’t get me wrong, I honestly think Carnegie’s main messages are sound. My one word review/summary of the book goes like this: Listen. A sincere appreciation in others and their interests and ideas is a respectable psychic muscle to cultivate. Reciprocating smiles, making others feel important, seeing through alternative perspectives — all great stuff. Ingenious, truly common sense stuff that is worth learning for your social consciousness.

But I think I was off-put by the cold categorizations and the systematic nature of these interpersonal “strategies.” Gamifying human emotional connection felt wrong. Perhaps that’s just because it was my first experience with the self-help genre and its style of communication; perhaps because the language was from a 1930s businessman and professional persuader. Either way, despite the commonsensical nature of these points on how to get closer to people, the ultimate motive being “winning” friends and influencing people felt manipulative.

I believe, then or now, making friends to be its own reward. Engaging in sincere, heartfelt conversation is an intrinsic good in no need of any ulterior. I want to influence people, sure — but much more so I wish to know them, to understand them. These are moral viewpoints.

Self-help in general has long struck me the wrong way. No matter the messages, it can come off as at best too optimistic, with inspiring words sung for their own sake — and at-worst sociopathic, manipulative, self-deceiving. Call me cynical. Or hypocritical, I’d be lying if I said I haven’t received value and enhanced social skills from books like How To Win Friends, The 7 Habits of Highly Effective People, Man’s Search for Meaning, The Miracle of Mindfulness, The Four Agreements, The Obstacle is the Way, various Jungian texts, King, Warrior, Magician, Lover, The Way of the Superior Man, etc. (Yeah despite my misgivings, I’ve read some self-help over the course of my life).

I’m just saying there are worthy criticisms to texts like How To Win Friends and Influence People.

And yet here I am, a writer who often touches on self-improvement topics and mindset tactics, set to add another entry into the manipulative mythos of interpersonal trickery. (sarcasm!)

I want to talk about conversations, their science and art. Influenced by personal experience, certain cultivated skills — and the majesty of cinema — here are my 3 tips on the art of conversation. Good, worthy, fun conversation. Meaningful conversation.

Simply, I am a man that enjoys conversation. I would not be writing this unless that were true. Here, I want to break down the why’s and how’s of it.


Use ’em.

Listen to people!

First and foremost, conversation is all about listening to your partner. Or, to the circle. Carnegie was right in the notion that you win friends and influence people by not making everything about yourself. And listening can be the easiest, most unselfish way of beginning to do so.

In friendship, business, marriage, sports, whatever — listening is the alpha and omega. If you aren’t listening, it’s not a conversation — dialogue becomes monologue. If you aren’t listening, you might as well be talking to yourself.

As a baseline in human communication, listening builds healthy relationships.

Everyone has probably heard of “active listening”; it’s not just a buzzword, genuine listening is a really important skill worth building up in all your relationships. It requires attention and focus, a conscious absorption of what a person is saying AND why. Every true conversation requires the investment of active listening.

At base, truly listening is an admission that you don’t know everything. And you don’t! Beforehand, you never know what people will say — even if you think you do. You never know what you may learn from someone, even if you think you know everything about them (and even if you don’t care to and don’t wish to change that fact).

What’s that saying? Everyone knows something you don’t.

It’s true. And the only way you’ll ever learn anything is by listening.

More than these benefits to you, listening is an imperative component of conversations and relations both for what it does to the other person: People want to feel heard.

Remember how listening is ultimately an unselfish act, a benchmark for healthy relationships? Even if you have no intention of accepting their notion, moving forward with it, or keeping your own mouth shut for a second longer — everyone in a conversation wants to feel like the words that have come out of their mouth were consciously acknowledged by the other party.

In sum: Make sure you listen to your conversation partner and ensure they feel heard.

Needless to say, what you say after someone in a conversation will, in part, be dictated by what you heard from them. And you have to listen to hear. That is science.

Listening is the foundation of good conversation — and real communication. It’s barebones stuff. Work on it before even considering how you speak or what you’ll say.

If you listen to people, all conversation becomes more natural. Even if you don’t like everything you have to hear, listening will help you cast sound judgments. More than likely, you will be surprised by how much people are willing to share when you let them.


A Lady Joker 😍

I actually love being surprised. It’s one of my favorite reactions. Even when it’s something not so good, surprise provides novelty. Originality.

In every conversation, I try to be original. Or, at least I hope to provide something original to the interplay of language being brought to the air between us. In this life, I try to be an original.

In conversation, I want something new, from me and from you (hey, that rhymed!) 

I wish to convey something the other person in the interaction may have never thought of. Not to impress them, though that may be a byproduct, but to give the conversation a chance to… be good. Engaging, fun, interactive. All that good stuff.

If I can submit something original to a conversation, then I’d probably consider it a success on that fact alone.

Let me back up. I have a strange obsession with originality. I know this wholeheartedly about myself; I have a lot of personal conviction in this regard. Perhaps this comes with the territory of being a writer, or just someone who has watched many movies. I desire originality not just with my consumptions, or my creations — but also my conversations.

This “tip” is quite personal. Perhaps self-revealing. I crave originality in thinking, writing, speaking – at practically all times. And I detest having to ‘state the obvious.’ (I understand this can get me in trouble.) I am a very naturally curious – and neurotic – person.

And have you yet considered the fact that originality is a key component in all good humor? Everyone likes making people laugh. And people laugh because they heard something original.

Please do not misunderstand me. A drive toward originality in conversation does NOT mean I cannot enjoy small talk. I can and do. However, like in any good episode of The Twilight Zone — there’s eventually gotta be a twist. Some novelty must be drawn up in every conversation, if that convo is to be named as *good.*

I realize I’m in danger of doing systematized, sociopathic ‘science’ on something as commonplace, and often necessarily mundane, as conversing with other human beings.

Obviously, not every conversation needs to broach true novelty, or be edgy just for the sake of surprising someone into a reaction. Don’t be annoying. You don’t always have to introduce yourself as The Joker.

Conversations sometimes just have a job to do, without any theatrics, critical thinking, or laughs. Not everything you say can be original; is anything truly original any longer?

My point here is that I try to approach conversations of a certain length as more than just an exchange of words and information and emotion.

I converse to learn. To search for new ideas and ways of expressing myself. If I am looking to talk, I want to do it with a sense of imagination and intrigue, poise and rationality. I aim to engage conversations with good humor and an open mind, always. I converse to understand and be understood.

In all these ways, I always, always converse with originality in mind.

That’s it.

Sorry, I don’t really have any concrete way of saying how to go about being original consistently. I guess I do it unconsciously at this point. And I’d never deign to say I am a master conversationalist with unforgettably original chops. Yeah, no. But being original in conversation is a core ideal of mine that I carry into every relationship I can.

I have no secrets to originality in conversation-making, or creativity in writing, outside of this: Listen and learn as much as you possibly can.


Meaningful conversation is the endgame, isn’t it?

It must be. Meaningfulness is what a human being desires in all things in this life. Not to get too metaphysical here, but the search for meaning and love and purpose beyond ourselves is what separates mankind from the rest of the animal kingdom. Meaning is the great difference maker. I’d reckon it’s the key to our whole consciousness.

So how do you go about making meaningful conversation?

Like anything great and challenging and *meaningful* — it’s easier said than done. Pure art, not a science.

What’s it all really mean?

First, meaning does not have to arrive on the heels of some great insight. You know, like a really good answer to a question like “what’s the meaning of life?” or “what’s your secret to beating Malenia, Blade of Miquella?” (Answer 1 = to give life meaning; Answer 2 = suffering. You’re welcome.)

Meaning comes from understanding.
Meaning comes from true communication between people.

A meaningful conversation is borne when you hear someone — and you understand what they are saying, why they are saying it, and where they are coming from. (Or at the very least, you have a desire to learn more in all those directions.)

And THEN, based on all that understanding, you speak something original into existence in response.

Rinse and repeat. Meaningful conversation means to continue the conversation and further delve another person’s soul along these lines.

Meaningful conversations are built on a foundation of apriori curiosity. That is, meaningful conversation comes from intrinsic motives, from the very base human desire to indulge another consciousness.

Meaningful conversation comprises every context you can imagine. Not just the words a person is saying, but how they are being said, in terms of body language, tone, posture, etc. — and why they are being said now. Understanding always requires active listening with an open mind, and some compassion. It’s a time-consuming process too. It takes effort and the threat of a mutual knowingness, some misunderstanding, even an end to the relationship itself.

We layer our words with meaning in the hopes that they are understood. When they are, we have realized a meaningful connection through the conversation. Good, bad, or indifferent. Positive or negative in effect. Meaningful conversations are not derived by the nature of our emotions in and of themselves, but from out of the consciousness of a true connection between human beings.

I hate to speak in so many generalities here but I don’t quite know how else to speak on this multivariate ideal of “meaning.” There can be no simple explanation for “meaning!” Partly because it’s a little different for everyone and partly because it’s one of the core mysteries of the human condition.

Oh yeah, the thought of *examples* brings me to the original inspiration for this writing. I originally conceived of my thoughts on this topic from an entirely different angle — not self-help but cinematic analysis.

The original title was simply “The Art of Conversation” and it was going to be a stream of consciousness essay on the best conversations in film history. From my singular perspective, obviously. 

We’re talking Pulp Fiction (1994) (or any Tarantino), Heat (1995), A Few Good Men (1992), When Harry Met Sally (1988), Stand and Deliver (1988), The Sting (1973), The Color of Money (1986), Before Sunrise (1995), Eternal Sunshine of the Spotless Mind (2004), etc. Maybe more by the time I got around to brainstorming my take on it and structuring my thoughts into a coherent essay of some kind.

Uma Thurman in Pulp Fiction (1994)

Somewhere along the way, I decided talking about specific conversations is way less interesting than experiencing them, or watching them on the big screen. Instead, why not turn the writing into a clickbaity self-help piece on how to make “good” conversation? (Whatever that really means.) Write it with 3 main points you can speak on plainly and in general terms that anyone can understand.

I then came up with 3 core components of what I think makes for good conversation, jotted them down, and shifted my thinking on the matter.

And now I’ve written the article. You just read it. 

Don’t get me wrong, I wrote this using my real knowledge and skills, my genuine convictions and beliefs about a topic like the “Art of Conversation.” I’m not pulling your leg here or trying to be disingenuous. I mean what I say; I just got here a little strangely is all.

All this transparency in my writing process is mainly to say that meaningful conversation must be self-discovered through genuine experience.

And now I’ve written enough to have earned my ability to say that.

My last drop of trope-y self-help advice for you is this:

If you want to begin to understand what makes meaningful conversation, go watch classic films with your friends. Read literature and start a book club. Travel and meet some new people in some new places.

Seek out meaningful experiences in your life and I’d reckon you will soon be having meaningful conversations every single day without even knowing it. ~