How to Ruin a Great Conversation

A Guest Essay by Brian Daskam

“Three Young Women” by Vilhelm Hammershøi, 1888

For the past 20 years or so I have had the privilege of living in close friendships with people who are willing to talk about things that matter. We have developed the habit of meeting together, mostly in living rooms, to talk about what it means to live well as human beings. In our years together we have enjoyed searching discussions and lively debates. We’ve also learned several ways to ruin a great conversation. Here are just a few:

1. Replace curiosity with curiositas.

2. Treat therapeutic self-disclosure as the zenith of intellectual intimacy.

3. Assume that talking about great books is the same thing as having a great discussion.

4. Allow your conversations to become sclerotic.

5. Focus on the form of your conversations to the neglect of the content.

“I mean, look at it, Q: look at all those culs-de-sac, those streets that turn in on themselves, all the houses that were built to fall apart. All those paper people living in their paper houses, burning the future to stay warm. All the paper kids drinking beer some bum bought for them at the paper convenience store. Everyone demented with the mania of owning things. All the things paper-thin and paper-frail. And all the people, too. I've lived here for eighteen years and I have never once in my life come across anyone who cares about anything that matters.” ― John Green, Paper Towns

The speech quoted above was delivered by Margo Roth Spiegelman, the manic pixie dream girl neighbor that the protagonist “Q” chases throughout the book. Paper Towns is not a serious novel by the standards of Luke’s readers. Yet that last line has stuck with me. “I have never once in my life come across anyone who cares about anything that matters.”

I want to live in such a way that the people around me say, “I have never once in my life come across anyone who cares about anything that matters except maybe Brian Daskam. He repeats the same stories and laughs at his own jokes, but he is willing to ask you about things that matter.”

When I host, plan, or participate in intellectual gatherings, my purpose is always this: I want to escape the condemnation of Margo Roth Spiegelman. I want to talk about “anything that matters.” 

Having a purpose for gatherings is more than just a source of inspiration. In her book The Art of Gathering, Priya Parker explains why gatherings benefit from a guiding purpose. “The first step in convening people meaningfully: committing to a bold, sharp purpose.” She says that a clearly defined and specific purpose will help determine all the small decisions that make up an event. The event’s purpose can serve as a “bouncer” that excludes elements of your gathering that don’t belong there. 

A caveat: The items I list below are dangers faced by those of us who are trying to host or participate in conversations such as salon dinners, reading groups, retreats, and the like. These five dangers won’t necessarily all apply to less formal occasions; for instance a double date or a phone call with your sibling. Those can still be great conversations, just a bit different from what I have in mind. Furthermore, the dangers discussed below are likely to bedevil those who are truly seeking to build communities where good conversation thrives.

With that said, let’s look again at those five ways to ruin a great conversation and consider how committing to a purpose can protect against them.

1. Replace curiosity with curiositas.

“Now all the Athenians and the strangers visiting there used to spend their time in nothing other than telling or hearing something new.” - Acts 17:21

A few years ago, one of my close friends began telling me about his doubts and questions regarding his Christian faith. Separated by over 2,000 miles, we shared a Google doc where we typed out a conversation regarding ethics, faith, and biblical interpretation. Eventually, we met up with a half dozen of our friends at a log cabin on the Puget Sound to explore these issues in person.

One evening we landed on a topic you might call “personal epistemology.” What is convincing to you? What kinds of evidence or arguments tend to make you rethink what you believe? For him it was all about stories. Compelling narratives, more than anything, grabbed his attention and made him consider new perspectives.

I admitted my own preference for the slightly obscure. If you want to convince me to your side, try citing an Eastern Orthodox monk that no one has heard of, or a fact from neuroscience that’s seldom discussed beyond academia. It’s not as if I’ve exhausted all of the wisdom of well known books. It’s just that I identify with “the Athenians and the strangers” from Acts. I too would like to hear something new.

Curiosity enables good conversation, and it’s hard to imagine genuine dialogue without it. But if curiosity is a virtue necessary for good conversation, curiositas is a vice that makes it all but impossible.

By curiositas, I refer to that perennial temptation towards intellectual novelty. It’s the desire to hear something esoteric, scandalous, clever, counterintuitive, or surprising. The conversation driven by curiositas subtly shifts the focus from understanding to entertainment. And once that shift in focus occurs, it’s difficult to undo. So how do you know if the conversation you’re participating in is one of curiosity or curiositas?

To resist the lure of curiositas, first, recognize that you are unlikely to diagnose anyone but yourself. This is a question of motives, and it’s difficult enough to understand your own motives, nevermind anyone else’s. Next, try to notice what interests you and motivates you relative to a specific topic. Let’s say you are in a discussion about faith, popular culture, and Charles Taylor’s concept of the social imaginary. It’s worth asking why you are interested in that topic. Do you think Taylor can offer real insights into your own beliefs and those of your neighbors? Do you want to better understand our social reality as compared to previous centuries? Or do you derive some pleasure from the knowledge that Taylor writes dense books referenced by intelligent people and by talking about his ideas, you resemble those models of intelligence?

“It’s a mix of those things,” I hear you say. “We will never have completely pure motives this side of heaven.” Fair enough. Nevertheless, curiosity and curiositas represent a fork on the path. To take the direction of curiositas is to become like those Athenians and visitors who spent their time in “nothing other than telling or hearing something new.” The conversation could be fun. You might sound impressive. But what would Margo Roth Spiegelman say?

2. Treat therapeutic self-disclosure as the zenith of intellectual intimacy.

“Alas! there cometh the time when man will no longer launch the arrow of his longing beyond man…” - Nietzsche, Thus Spake Zarathustra 

I once attended a meeting in Chelan, Washington. It’s a pleasant town, built around a lake, ringed with mountains, and dotted with wineries. Over appetizers and drinks, I introduced myself to one of the attendees, a man a few years younger than me. He spoke to me about how he suffered from seasonal depression and how his wife also struggled with depression and how these overlapping mental health challenges had left their marriage reeling. They were working on it, and he was optimistic, but recognized that they had a long road ahead of them.

It’s been a few years since that meeting, and I hope he and his wife are doing well. The odd thing about that interaction was that I had disclosed nothing personal to him. He was entrusting me with some very personal information that I hadn’t earned. What motivated that?

I have a rather underdeveloped theory that goes like this: Every enjoyable conversation feels a little like a conspiracy. A family telling inside jokes at dinner, office mates gossiping together after work, a couple huddled together in a restaurant booth… Each group is a distinct caucus in which each member is known, and each member belongs. Or, put another way, anyone who is not part of the conversation is an outsider. That feeling of belonging is one of the key pleasures of great conversation.

If that’s right—if being known is one of the pleasures of great conversation—it’s only natural that we would want to understand and be understood by the people around us. For those of us who have come of age in a time where therapy-speak is the common vernacular, being known may seem to begin and end with talking about mental health.  

I don’t begrudge anyone talking about their mental health. It could be exactly what they need and perhaps it will lead to closer friendships. Who am I to judge? But here’s why I take the risk of bringing it up: Conversation has the potential to go well beyond our individual emotional states. C.S. Lewis spoke of the “golden sessions” where “the whole world, and something beyond the world, opens itself to our minds as we talk.” Heinrich Wiegand Petzet, after attending a lecture by Martin Heidegger exclaimed, “The things of the world lay open and manifest in an almost aching brilliance…. for a brief moment I felt as if I had a glimpse into the ground and foundation of the world.” To engage in deep and meaningful conversations will require us to look beyond ourselves, to inquire of the mysteries of the universe, and (in Nietzsche’s phrasing) to launch the arrow of our longing beyond ourselves.

3. Assume that talking about great books is the same thing as having a great discussion.

“Philosophy begins in wonder. And, at the end, when philosophic thought has done its best, the wonder remains.” – Alfred North Whitehead

I recently participated in a discussion on the topic of beauty, hosted by Drink & Think. Attendees were invited to consider such questions as “What is beauty?” “Does beauty matter; and if so, why?” One person’s hand shot up early in the discussion. "Beauty is truth, truth beauty,” he said, quoting the line from Keats’ Ode to a Grecean Urn. “That is all ye know on earth and all ye need to know."

Maybe this guy arrived at the night’s discussion with the quote memorized–an arrow in his quiver that he was determined to use. I can’t blame him for that. I have certainly done the same. But it’s worth noting how a quote like this can substitute for thought rather than facilitate it. 

Great text’s have an earned reputation for being thoughtful and thought-provoking. Reading and discussing them, it follows, tends to be an intellectually productive exercise. So in a group discussion on a big idea, it tends to be helpful when someone references Hume or Plato or Shūsaku Endō. The challenge for the moderator is to make sure that talking about great books doesn’t become a way to evade great discussion. 

We should include the great thinkers of the past in our conversations and let them help us fulfill our purpose of talking about things that matter. We shouldn’t let their names or ideas become a substitution for humble curiosity. 

4. Allow your conversations to become sclerotic.

“What if we… really inhabit an era in which repetition is more the norm than invention; in which stalemate rather than revolution stamps our politics; in which sclerosis afflicts public institutions and private life alike; in which new developments in science, new exploratory projects, consistently underdeliver?” –

Ross Douthat

The quote above comes from Ross Douthat’s critique of our society as one that has fallen into decadence. In his telling, our culture has passed its glory days and we are more or less marking time as we wait for whatever comes next. The result is exhaustion, frustration and repetition at the societal level. The sclerosis he refers to can also occur, I think, at the level of a small group. 

You probably have some relationships that follow this pattern. There are individuals or groups with whom you’ve made a silent agreement. Three or four topics are open for repeated discussion. A half dozen stories or so will be retold and warmly received. There’s a movie quote or two that gets an automatic laugh. And really, this might be a fine way to faithfully maintain some friendships or familial relationships. The conversation may be predictable, but at least you’re still talking. The same is not true if you are ambitious for great conversation. 

Sherry Turkle made a provocative observation in her 2016 book Reclaiming Conversation: The Power of Talk in a Digital Age. She claimed that it takes seven minutes for a conversation to really get good. In those first seven minutes, participants are mostly giving standard answers to one another’s questions. However engagened and genuine they may be, their conversation is inevitably a kind of cut and paste from previous things they’ve said, thought, or read. But something else is possible beyond that seven minute threshold. Genuine discovery can take place. The participants can stop monologuing at each other and actually begin to explore. That exploration can be exciting and uncertain, and it can generate more questions than answers. But it also tends to be energizing for everyone involved.

One practical way to keep your group discussions from becoming sclerotic is to regularly involve new people. New participants won’t have your same assumptions or reactions, and so they can help you break out of conversational ruts. 

5. Focus on the form of your conversations to the neglect of the content.

“The self, that dear and brief acquaintance, we could entertain with a little of the ceremony it deserves.” – Marilynne Robinson

In the years that I worked with conference planners, I was regularly surprised by the degree to which the attendees cared about creature comforts. They invariably had strong opinions on the temperature of the rooms, the comfort of the chairs, and above all the quality of the food. Those conferences were planned for months, with careful consideration of session topics, schedule, room sizes, and every other detail. But when the evaluations came back at the end of the conference, those very physical aspects were mentioned more than anything.

As a discussion host, you are likely to put a lot of time and thought into being hospitable. You’ll work to make sure that your guests are comfortable and to eliminate distractions. After you’ve hosted a few gatherings, you might begin to feel that you have “the system down.” You know how to arrange the chairs, where to set out the drinks, and the perfect volume for the music.

In all of this hospitality, make sure you are setting aside enough time to think through the discussion topic and to contemplate it with the wonder and curiosity it deserves. It’s great to get the logistics and the format of your discussions figured out. But don’t suppose that a flawless conversation is the same thing as a successful one. Instead, develop a ambitious dissatisfaction in the level of discourse you are participating in.

Consider Margo Roth Spiegelman. If she were to join your discussion, what would she say? Would she have to amend her statement and admit that there is a group of people who seem to genuinely care about the things that matter?

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Brian Daskam is the Director of Communications at the Trinity Forum and lives in Denton, Texas.