Perhaps our imperfections in conversation aren’t flaws but features

About the conversations that shape us

detail from ‘Judith Beheading Holofernes’, Caravaggio, 1599

Proust and Joyce met only once, at a dinner party at the Ritz in Paris in 1922. Both were literary giants of their time, absolute masters of capturing the nuances of human interaction in their writing. They were seated next to each other, but their conversation was reported to be flat and awkward, bogged down by trivial talk of ailments, chauffeurs, and truffles, both repeatedly answering with the lonely word: ‘Non.’¹

Their encounter certainly wasn’t a grand dialogue and exchange of ideas as one could have expected between these two great minds. But perhaps that’s the point: conversation isn’t a performance or controlled act of composition akin to their brilliant writing. Their awkward exchange can remind us that conversation is alive and human, precisely because it resists control and perfection.

If conversations aren’t about flawless articulation, then what does make them meaningful? It’s often the moments when something real breaks through, like a moment of raw honesty, or hesitation, or when something new starts forming in the space between two minds.

But what if we’re bad at talking (and that’s a good thing)?

We can perhaps view our imperfections in dialogue as features, rather than flaws. The mentally replayed dialogues that we silently scold ourselves over later. Looking back, my most meaningful conversations were never polished performances. What made them matter was my ‘okay-ness’ with the fumbling, because that wasn’t the point.

They were conversations when I could step out of the presentation mode², this reflex to perform or sound clever to impress. When I could push back on my overly self-conscious or performative ego that would have otherwise blocked what I did end up saying, or truly receiving what I heard the other person say. Messy and nonlinear, yes, but also surprising and real.

What is it about strangers?

If imperfection makes conversation more alive, maybe familiarity isn’t a prerequisite for meaning either. Some of the most resonant conversations don’t even happen with those we’ve known for years, but with people we’ve just met. There’s a curious paradox at play here. We assume deep conversations require deep relationships, yet sometimes, the very lack of history is what allows us to speak more freely.

I remember the cab driver or stranger next to me on the plane who became my confidant, even for just a short but weirdly intimate window of time. Like mini (well, and less romantic) episodes of Midnight in Paris. Rather unexpected, yet deeply open and rewarding conversations. This is also known as the “stranger-on-the-train” phenomenon: we may disclose intimate details to strangers more easily due to our lower perceived risk of judgment or future repercussions. It’s as if strangers offer us some shortcut to intimacy, when we are able to discover new aspects of ourselves through the exchange. It’s not that strangers understand us better, but that we are momentarily unburdened by our own narratives.

Conversation as an active introspection

The word conversation comes from the Latin conversari, meaning to “to dwell with” and “to turn toward”: not only toward one another but toward unfolding thoughts, emotions, and questions within ourselves. In this sense, conversation is an inside out process: the more we’re willing to engage with what’s unfolding within us, the more authentic and meaningful our connections with others become.

Conversation can then become a process of thinking and feeling in real time, an exchange where our curiosity leads and nudges us to ask: What do I think about this topic, and how do I feel about it? In such exploration, we don’t just exchange ideas, but may actually discover new parts of ourselves that just weren’t quite as clear to us before.

So again, meaningful conversation isn’t much about getting all the words right, but to stay in the exchange long enough for something novel to emerge. Something neither person could have arrived at alone.

The co-creational power of conversation

When conversations unfold based on their own, energetic momentum, they can build their full power: this process of co-creation, where something novel is emerging in real time, in the process of exchange between two (or more?) minds.

Poet William Wordsworth described the creative process as ‘half-perceiving, half-creating.’³ To me, this applies also to the nature of transformative conversation, in which ideas take shape through the act of articulation. In this dance between listening and speaking, discovery and expression, it’s like witnessing the live creation of a new stepping stone of my understanding, its contour only becoming visible during (and often also post-) dialogue. Like the reaching out with my hands in a dark room. And I guess that’s the edge of conversation between chaos and order: the space where I don’t just exchange something repeated or rehearsed, but help (or am helped to!) crystallize something new.

The middle way of conversation

When we are in conversations that challenge us, there can be the reflex to either reject what we hear out of defensiveness, or to absorb what we hear into our worldview.

But there’s also a middle way approach. I can treat something challenging or even hurtful more as a mirror instead of a directive. The real question then isn’t whether to accept or reject something, but rather to feel into how something resonates within us: Do I feel myself contract or expand in response?

I believe that at its core, everything in life - in conversation as well - comes down to fear and love. The discomfort I felt in some conversations were at times a mirror of some of the fears I wasn’t facing. When I lean into this discomfort of a conversation, for example when I talk about grief or more hidden feeling, I experienced coming out of such conversation feeling so alive. There is, after all, something luminous in the moments when we turn toward the raw edges of truth. It’s when I was able to feel the human connection, and the energetic resonance and warmth from being seen.

The playful risk of “Yes, and…?

With his middle way, we may also create more space to lean into the inherent unpredictability of conversation. Dialogue isn’t just about careful listening and speaking, but also about play and risk.

In improv theater, the golden rule is “Yes, and….” In playful, improvised exchanges, participants accept what’s offered and build on it, and this also applies beautifully to conversation more in general: when we approach dialogue with a playful, improvisational spirit, we open ourselves more to the unexpected. In moments of improvisation - again, non-rehearsed - something spontaneous and novel reveals itself. And sometimes surprising not only the listener(s).

The role of silence: letting the gaps speak

Awkward pauses in conversation—how often have they unnerved me? That reflex to fill the air and smooth over the void with word is almost instinctual. But I think the discomfort isn’t in the silence itself but in our resistance to it. In reality though, good conversations should be allowed their natural rhythm, their interplay of speech and silence. Because both are equally essential.

Silence isn’t something we need to frantically push away. Instead, maybe, we can try to think of silence even as this: rest. David Whyte describes rest as “the conversation between what we love to do and how we love to be.” What if we approached silence in dialogue the same way? Instead of treating it as an unwelcome interruption, we can try to be a bit more relaxed, allow it to settle and do its quiet work. While in return letting us doing this: simply being in the moment with the other person. I have experienced this as particularly important when being with someone who is grieving, and that my caring was more felt and unfolding when I allowed myself to sit in what at first may have felt uncomfortable.

Conversation can then become this more embodied listening, to whatever quietly wants to unfold, during and after.

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Perhaps this is what conversations ask of us: not just to speak, but to listen more deeply. To not just “perfectly” answer, but to follow more the questions, allow something new to emerge - despite all our flaws and imperfections. And lastly, to remain humble and a bit more (self-)forgiving if we still fail at successfully articulating certain things, especially those that are lodged deeper in us.

Give it space, the shaping will follow naturally.

This piece wouldn’t exist without the many conversations that shaped me and the conversations that shaped this essay. Thank you

Marie Friberger

,

Simon Emslie

,

Dana Allen

, and

Rachel Parker

for your reflections, suggestions, and the generosity of your time with editing help.

I want to practice what I write, so I’d love to extend an invitation: if this piece resonated with you and you’d like to have a “spontaneous” conversation with me, please reach out! Let’s have a “conversation among strangers” ha, and schedule a call - no agenda, no script, just see what emerges. Talking about writing and Substack alone is always fun.

1. This first read about this encounter in Alain De Botton’s book How Proust Can Change Your Life (1997).

2. Philip Sheperd writes about this presentation mode in his book Radical Wholeness, The Embodied Present and the Ordinary Grace of Being (2017)

3. The Matter With Things, Iain McGilchrist (2021)