When is the last time you had a great conversation? A conversation that wasn’t just two intersecting monologues, which is what passes for conversation a lot in this culture? But when you last had a great conversation, in which you overheard yourself saying things you never knew you knew, that you heard yourself receiving from somebody words that absolutely found places within you that you thought you had lost, and a sense of an event of a conversation that brought the two of you onto a different plane, and then, fourthly, a conversation that continued to sing afterwards for weeks in your mind? And I’ve had some of them recently, and it’s just absolutely amazing. They’re like, as we would say at home, they are food and drink for the soul.
– John O'Donohue (On Being with Krista Tippet) 
Virtually every time I see Dave Perell, we have remarkably deep and memorable conversations. It feels as though you sucked up all the most interesting bits of your day’s and week’s and life’s conversations – those bits you quietly hope to stumble upon as you wade into any conversation – then bottled them up and released them into a two- or three-hour sprint at your local Starbucks. It feels like, in mere hours, you traverse the gamut of human experience, covering far more territory on the plane of ideas than you ever could on the plane of reality. It’s as if you hit reality’s escape velocity, no longer bound by the rules of space and time – and in a sense, you aren’t: this is how time truly flies.
I hadn’t seen Dave in a few months so I thought we’d mostly be catching up. I’d tell him what I’ve been up to and he’d tell me about his life. This is what I’m used to.
And though we did briefly catch up, Dave was eagerly waiting to break free from the tired rituals of personal exposition. At one point, he even cut himself short: “I don’t want to talk about me,” he said. You could feel his exasperation – the topic to him was inherently uninteresting. Although I couldn’t articulate why exactly, intuitively I agreed: I didn’t want to talk about myself either. That was boring.
When Dave suggested we move on to topics more interesting than ourselves, it struck me as highly unusual but also deeply correct. It felt as though he was engineering a good conversation – and he was right.
We quickly found a topic we both were passionate about, and then the rest of the conversation flew by. We bounced from idea to idea, from topic to topic, with a sort of physical energy you’d expect if you watched people fencing. There was no question-and-answer, no dumping of someone’s life story, no perfunctory head-nodding - just organic, lively conversation.
Several hours later, when we were wrapping up, Dave explained what he did. He said that when we’re talking about our personal lives, we’re really just searching for entry points into a shared experience - that feeling of “Oh, the same thing happened to me!” or “I totally agree!” In other words, the boring, uninteresting bits before we hit common bedrock were simply the costs of search.
Dave was seeking launch points. He was evaluating which personal topics would elevate our conversation to a shared plane of reality – a plane of experiences and ideas and emotions with which we could really engage. By freeing us from the obligation to talk about our personal lives, he was making sure we didn’t spend the entire conversation searching for the good stuff.
This was fascinating to me because I had never thought of conversations in this way. I know what a good conversation feels like, but I didn’t realize how to get there. Now I see the small talk and the banter and the personal stories as simply launch points into something greater: shared experience.
When you think about it, this makes total sense. Whenever you’re “catching up” with someone, you’re often just dumping the details of your life onto another person. It’s as though the notebook of your life fell out of sync with the notebooks of others, and to compensate you hurriedly transcribe the notes from one notebook to the other. Then, the other person reciprocates. As John O’Donohue said, it really feels like two intersecting monologues.
This “life-dumping” offers no shared experiences – no shared context or understanding. I can’t feel what you felt or see what you saw – your experiences remain distant and confined to the narrow entrappings of first-person perspective. When someone life dumps, the other person feels the distinct sense of being on the outside looking in – of being a non-participating observer in someone else’s life story. Despite best intentions, it’s hard to truly connect.
To have an actual conversation then, we must escape our first-person experience. We must reach common ground – a shared reality in which we can both participate.
Sometimes, we get there emotionally through storytelling. Other times, we get there intellectually through ideas. But it’s precisely in this shared reality that we achieve a metaphysical closeness that no mere physical closeness can parallel, as though our souls rose from our bodies and fused into one. Your story becomes our story.
The act of sharing in ideas and feelings is perhaps counterintuitively far more personal than trading updates on our personal lives. We transcend the physical descriptions of what someone did and reach the metaphysical depth of who they are.
Shared realities also explain why good conversationalists are often vulnerable. They are inviting you to join them on the shared plane of human experience – one that includes our deepest emotions of fear and regret and pride and shame – emotions which we often don’t feel comfortable expressing. They open the door to our common humanity and invite you to walk in.
In essence, vulnerability engineers good conversation. Vulnerability appeals to our common humanity. In the real world, you and I may differ in every respect imaginable. But in the abstract world - in the world of beliefs and ideas and emotions - there is something fundamental that transcends all human division: divisions of language or race or culture or class. That something is the human condition. It is our primal beliefs in fairness and reason and competition, or emotions of pride and anger and revenge, all of which have been baked into our very existence over millenia of evolution. The common ground is there - with everyone; if you can’t find it, just go deeper.
Once you hit common ground, you know it. These shared experiences shape you - they “sing afterwards for weeks in your mind” – and they stick with you long after the physical presence of someone has gone.
Dave taught me that day that the goal of catching up is not to catch up. It’s not about talking about yourself – about transactionally giving your life updates and then receiving those from someone else. Instead, it’s about intentionally searching for launch points – conversational ramps we can use to reach a shared reality far more powerful and enduring than the one we physically occupy. It’s those shared experiences that make great conversation.
 Dave shared the quote from John O’Donohue with me and first mentioned it in his weekly newsletter here.