Mastering the Art of Conversation

Talking and listening. Pretty cool skills! Can be used for ordering coffee, for small talk, or for intense hour-long conversations on important topics like life, death, love, kittens, and bacon.

And while it’s very rewarding to turn a regular chat into an engaging conversation, it’s too easy to get stuck in small talk. This article contains some ideas on how to get out of the mundane and into the interesting.

Take 5 minutes to read it, then sit down with a human and start talking. Deep conversation guaranteed. Are you game?!

Catch the hooks

Every person exhibits many ‘hooks’ to bite, even before you’ve met them. Hooks are basically little chances for you to start asking for or telling about something. The better you are at catching them, the better you are at both initiating a conversation and keeping one going.

They can be based on appearance, like a funny hat, or on anything else you know or infer about the person. Guessing things can work too, and make for some funny conversations. You could for example ask “So where are you from?”, or say instead “It’s really cold and you’re not shivering, you must be from Antarctica.” You’ll get an answer anyhow, why not a laugh too?

When searching for ‘hooks’, keep in mind that every person has mundane stuff to tell about, like where they live, what they do for work, or how many siblings they have. However, every person also has character traits, has felt emotions, and made life choices. A lot of them. Talking about these nuances is exciting, and key in going from small talk to intense conversations.

For example, you could ask me where I live and what I study, or you could start asking about what quirky character traits I possess and I’d reveal to you how I dress up like a princess every Tuesday eve. (If I feel that you don’t judge me…) Dare to ask the more unusual questions and you will be rewarded.

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Branch off

When in conversation, you can branch off into uncharted conversational territory by talking about a new topic. But the other person might be confused when you first ask “so where you from?” and then start talking about how fluffy your new dog is.

Connecting new topics to the conversation must be done in a natural way, such that the other person is not confused and can stay fully engaged in the conversation. Half of the work is to make it sound natural, and if you do, the topics don’t really have to be that related. (Especially a few drinks in.)

This is quite powerful as it enables you to keep the conversation going indefinitely, and steer the chat towards any topic you want.

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People seem to like to listen to compelling stories. And, believe it or not, we can all be storytellers, simply by telling about our own life. Your life doesn’t even have to be extraordinary to yield hours of stories, it’s about telling the story in an interesting way, preferably while showing some emotion—sometimes the storyteller’s outcry is funnier than the story itself.

How about the time you tried to cut your own hair, that moment when you were amazed by that epic sunset, or that time you farted in church?

Remember that everyone tells stories in their own way, and that way needs practice to be developed. Give yourself a plus even when the story falls on deaf ears, because there is no practice without failure.

At this point, I can’t help you much more as I usually don’t really have an idea of what I’m doing when I tell stories. But hey, it seems to work, people laugh. Sometimes. When they really can’t stand the awkward silence…

First listen, then tell

In my opinion, the hardest part about conversing is listening. If the other person doesn’t feel listened to, it means he or she isn’t engaged, and no deep conversation will ensue.

That’s why I try to listen and ask questions first, and only then start telling about myself. My method for keeping my mouth shut is quite refined; I order the largest milkshake and start sucking the straw slowly and continuously. Try it yourself, it’s very effective!

Interruption is exciting

Interrupting someone can serve multiple goals: getting to a deeper layer of the story, making a remark, or avoiding falling asleep. If someone’s talking and you’re really losing interest, isn’t it just disrespectful to keep pretending to listen?

It might not be the best time to interrupt when someone is passionately telling a story—indicated by large, sweeping hand movements and strong facial expressions—but otherwise, respectfully interrupting to ask questions or react to funny details is no crime, and can actually serve to spice up a conversation.

Talking with anyone

Sometimes having a great conversation takes no effort at all. Sometimes it does, depending on the person, the mood, and the language barrier.

Truth is, good conversations are all around, waiting to be had. With friends, at work, in the bus, anywhere. A little effort is all it takes.

I think it’s one of the coolest things ever to sit down with a friend or stranger and share stories, laughs, emotions, maybe even make a new friend, and then walk away with a satisfied feeling: you talked to a human. A human being! Go on, close your laptop, find someone to talk with, smile a little, and talk about life and death and bunnies and such.