" /> an introvert's guide to meaningful conversations - Simply Olivia Grace
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Small talk is, quite simply, the bane of an introvert’s existence.

Why, you wonder, would you waste precious time of your life discussing the weather of the umpteenth time, when you could be talking about human nature or literature or something that matters?

More broadly phrased: in a world full of insincerity, how can we have honest, meaningful conversations?

Why It’s Harder Than Ever to Have Meaningful Conversations

We all know the feeling: you’re making polite conversation with someone you haven’t seen in ages and they ask a question—“How’s work?” or “How’s school?” or “What’s new with you?”—but you can tell they don’t really care about the answer. Already, their gaze is wandering around the room, looking for something more interesting.

If you’re tired of these kinds of exchanges, you’re not alone. More than ever before, it’s difficult to have authentic, meaningful conversations. There are a couple different explanations for the pervasiveness of small talk in today’s world.

First, most of our contemporary sense of “connection” comes from social media. Online connection, though, can leave us feeling lonely. Though being tagged in a post or receiving a text might be rewarding for a moment, those things never sustain a friendship longterm. On social media, we offer up our best self, the “highlight reel” of our life, the version we want others to see. Reality is far more complicated than the Instagram-perfect pictures let on.

Second, small talk is the default for our face-to-face exchanges. Our standard “go-to” subjects are usually the same: work, school, family, and the weather. We might want to talk about more meaningful things, but we’re afraid nobody cares enough to listen. It can be tempting to put on a brave face and pretend we have it all together, but that only leaves us feeling empty inside. Small talk is easy because it’s safe.

Both of these reasons boil down to the same answer: on social media and in small talk, we like to pretend we have it all together. We offer our best selves to the world, hoping no one will look too closely and notice that (spoiler alert) we have no idea what we’re doing.

friends, small talk, conversation

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What Do We Really Want?

In Dale Carnegie’s book How to Win Friends and Influence People, he lays out a simple premise: every person wants to feel important. We all want to be known, recognized, appreciated, and liked for who we are.

Every person has worlds within them. On the surface, there’s the conscious information about who they arelikes and dislikes, hobbies, favorite things, how they spend their time, people they hang around. On a deeper level, there’s the unconscious things that make a person who they are—their beliefs, values, childhood memories, experiences that shaped them as a person, ideas they think about, their favorite song lyrics, the struggles they rarely open up about.

When it comes to friendships, it’s the same idea: we want to be truly known. We want to be completely accepted for who we are, with all our imperfections and quirks and flaws. Everyone is looking for friendships that will last for years and years, the kind of friendship forged through shared experiences and late night discussions. We want friends who will be with us through all the ups and downs of life, who encourage us along the way, who believe in us when we don’t believe in ourselves.

The Key to True Connection

A few years ago, I encountered a TED Talk by Brené Brown that has stayed with me since. You can watch the full video below, but essentially, Brené Brown suggests that being vulnerable is the only true way to forge true connection with others.

When you have the courage to be imperfect—to laugh when you mess up, to quietly know your worth, to learn from your mistakes and move on—life is easier for you and everyone around you.

The Right Questions for Meaningful Conversations

How do we begin meaningful conversations about things that matter to us? How do we skip the small talk and get straight to conversations that help us truly get to know each other?

Like any skill in life—public speaking, riding a skateboard, playing the piano—becoming a good conversationalist is something that takes practice. Here’s the secret: the more honest and vulnerable you are with others, the more honest and vulnerable they will be with you. 

If you really want to get to know someone, ask open-ended questions that give them space to answer authentically. Avoid asking questions with “yes” or “no” answers. Don’t ask a vague question like “What’s new?” or “How are you doing?” unless you want an equally vague and uninteresting answer.

Instead, ask questions that open up a new direction in the conversation:

  • What’s the most exciting thing happening in your life right now?
  • What songs do you listen to on repeat?
  • What projects do you have going on?
  • Who are your role models?
  • Who inspires you most?
  • What makes you feel fulfilled?
  • When do you feel most alive?
  • What books changed your life?
  • Have you ever seen a miracle?
  • If you could travel anywhere in the world for a week, where would you go?
  • What’s on your mind these days?
friendship, conversation

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Be the Friend You Wish You Had

“If a man is worth knowing, he is worth knowing well.”

—Alexander Smith

Before you can find true friends—or “kindred spirits,” as Anne Shirley would say—you have to be a true friend. It starts with you! Become the kind of person you’d like to be around. Smile at everyone who passes by, introduce yourself first, give compliments, ask genuine questions, and really listen. In the end, it comes back to confidence. When you are sure of who you are, you unconsciously give other people permission to be themselves.

We are a lonely generation, but it doesn’t have to be that way. You can be the one to initiate meaningful conversations! Give yourself the freedom to be vulnerable, to show up courageously imperfect. Start by asking someone a genuine question, and truly listen to the answer. You’ll be amazed how quickly people open up, when they’re given the chance.