How to Have Meaningful Conversations that Connect

How to Have Meaningful Conversations that Connect

These days, we’re inundated with reports about our epidemic of loneliness. There are many contributing factors (wave hello to the device you’re reading this on right now), but one biggie is that we’re rapidly losing a cornerstone of connection: the art of meaningful conversation. Meaningful conversation is foundational to a satisfying life of the mind and to creating a culture that offers depth and belonging. 

Most of us would say a conversation that’s meaningful is a conversation that’s good. We know it’s pretty much the opposite of all those tweets that essentially come down to, I’m right, you’re wrong, end of story. But what specifically makes a conversation a good one? In the book, Talking Cure: An Essay on the Civilizing Power of Conversation, Paula Marantz Cohe says:

Good conversation mixes opinions, feelings, facts, and ideas in an improvisational exchange with one or more individuals in an atmosphere of goodwill. It inspires mutual insight, respect, and most of all, joy. It is a way of relaxing the mind, opening the heart, and connecting authentically with others. To converse well is surprising, humanizing, and fun.

So how can we converse in a way that’s surprising, humanizing, and fun? Here are a few tips:

  1. Remember, moving from superficial chatter to meaningful conversation isn’t just about probing for deep feelings or deeply personal experiences. A sense of connection usually starts with sharing ideas and opinions in a lighthearted way about a topic you love discussing. Getting good at sharing lightly about what matters to you makes it possible to have meaningful conversations with virtually anyone—you don’t need to have a lot in common. 
  2. Focus less on what the other person thinks of you or on trying to impress them and more on being curious about who they are. A lot of us will hear one thing that sparks our interest and then be eager to jump in and talk about ourselves. Before doing that, help the other person to feel seen and heard—a fundamental human need that most of us crave to experience a lot more. One good practice for achieving this is to ask at least two follow-up questions before sharing something about yourself. When people feel you are genuinely interested in them, they will perceive you as interesting and likable—no special knowledge or charm on your part is required. 
  3. Have you been in situations where the only question anyone you met seemed to ask was, “What do you do?” That’s a common conversation starter in cultures where people’s identities are heavily fused with their work. Unfortunately, it can also be a conversation stopper, bringing up self-judgment and putting us into comparison or evaluation mode rather than fostering curiosity, exploration, and a sense of fun. 

More interesting, heart-and-mind-opening questions include*:

  • What do you love to do? 
  • What do you do for fun?
  • What are you interested in?
  • Are you reading anything right now? What do you think of it?
  • Do you have any favorite places you love to go or places you dream of visiting? 
  • Who is one person, living or historical, that you would love to meet?

*After asking any of these, ask a follow-up question that shows you really listened, and then acknowledge what you find interesting about what the person said.

In our fast-paced world, it can be challenging to slow down enough to patiently delight in getting to know another. But for an Imperfect Intellectual, meaningful conversation is a peak experience—a skill we delight in practicing as our practice gradually adds more and more pleasure and meaning to our lives.

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