102. On the Art of Conversation

Very often Montaigne’s titles tell us nothing about what we should expect in the essay, but in this case, the title is important. The essay isn’t about discourse, it’s about conversation or more precisely, agonistic conversation.

The conversation Montaigne has in mind is lively and interactive. He hints at this in his Sebond essay, where he describes supporters of Pyrrhonism enjoying the give and take of argumentation, not particularly concerned who comes out on top. 

This is a thornier matter to discuss than it may appear on the surface. We like to think of debate as a discreet activity that takes place in the form of direct competition, whether it’s an event staged for high school or college, or an encounter that is part of an election season. But the importance of debate goes beyond this. Having a debate mentality is critical to Pyrrhonism and any belief system that requires a rigorous examination of ideas and expressions.

As Maurice Merleau-Ponty observes, Montaigne’s exploration of self is always tied to his engagement with others. Debate, for Montaigne, is not about victory but about what Merleau-Ponty calls the “mixture” of internal and external realities. In challenging others’ ideas, we confront our own biases and assumptions, inhabiting a space where self-awareness and external critique intersect.

Why does Montaigne believe we need debate? In this essay, gives us a rich catalog of reasons, starting with the simple truth that we never stop learning in life and one of the best ways to test both our ideas and style of discourse is to keep testing it:

Every day I am warned and counseled by the stupid deportment of someone. What hits you affects you and wakes you up more than what pleases you. We can only improve ourselves in times such as these by walking backwards, by discord not by harmony, by being different not by being like. Having myself learned little from good examples I use the bad ones, the text of which is routine. I strove to be as agreeable as others were seen to be boring; as firm as others were flabby; as gentle as others were sharp. But I was setting myself unattainable standards.

I recently came across this wonderful essay written by Irish novelist Sally Rooney about her days in international competitive debate. It’s one of the best pieces I’ve ever read about debate and so much of what she describes resonates with my experience of it, even if I draw more positive conclusions about it than she does.

While I love competitive debate, Rooney makes a few points that are valuable to keep in mind while examining Montaigne’s less systematic examination of debate. Rooney’s description of competitive debate as a ritualized and hierarchical activity contrasts sharply with Montaigne’s ideal of free-flowing and exploratory conversation. For Rooney, debate operates within rigid constraints: topics are predetermined, positions are assigned, and points are awarded based on performance rather than genuine understanding. The game-like nature of competitive debate prioritizes form over substance, requiring participants to master rhetoric while suppressing emotional and relational dynamics. Montaigne, by contrast, advocates for a conversational model where ideas evolve organically, driven by curiosity and a mutual desire for growth. His vision of agonistic conversation values the unpredictability and serendipity that arise when participants are not bound by rules but by a shared commitment to exploring truth. Where Rooney’s debate is performative and competitive, Montaigne’s conversation is collaborative and open-ended.

Both Rooney and Montaigne recognize that intellectual engagement, whether through debate or conversation, serves as a medium for self-discovery. Rooney’s experience of “flow” while debating—the feeling of effortless immersion and connection between thought and expression—mirrors Montaigne’s emphasis on the transformative power of dialogue. For Montaigne, encountering opposition sharpens self-awareness: “When I am contradicted, it arouses my attention, not my wrath.” Similarly, Rooney acknowledges that the structure of debate forced her to examine ideas she might not have considered otherwise, even as it revealed her capacity for strategic aggression and rhetorical manipulation. However, while Montaigne celebrates contradiction as a path to wisdom, Rooney’s reflections highlight the limitations of debate’s competitive framework, which often prizes cleverness over authenticity and leaves little room for the vulnerability that genuine self-discovery requires.

But having pointed out those potential alignments, it’s also important not to soften Montaigne’s view of debate too much. For Montaigne, debate is a profoundly embodied experience, akin to sparring in a physical sport. As Merleau-Ponty notes, Montaigne’s philosophy resists the Cartesian separation of mind and body; instead, his debates are lived experiences where thoughts take form through interaction. This emphasis on the physicality of conversation underscores its role in shaping both the mind and the self.

Montaigne thought this physicality was vital, providing something that cannot be found in reading. We need lively conversation to test the ideas we’ve read and to integrate them into our other thoughts. Intellectual competition for Montaigne is akin to sports:

Studying books has a languid feeble motion, whereas conversation provides teaching and exercise all at once. If I am sparring with a strong and solid opponent he will attack me on the flanks, stick his lance in me right and left; his ideas send mine soaring. Rivalry, competitiveness and glory will drive me and raise me above my own level. In conversation the most painful quality is perfect harmony.

Montaigne is clear that he doesn’t enjoy debating just anyone — and debating the stupid can be an exhausting experience. There’s a level of respect we accord to anyone who we agree to debate, which is why heavily favored candidates rarely allow their opponents the honor. Attaining this kind of agreement, Montaigne would reject the contemporary custom of highly structured rules and would prefer a lively event:

Among gentlemen I like people to express themselves heartily, their words following wherever their thoughts lead. We ought to toughen and fortify our ears against being seduced by the sound of polite words. I like a strong, intimate, manly fellowship, the kind of friendship which rejoices in sharp vigorous exchanges just as love rejoices in bites and scratches which draw blood.

This raises one final important contrast between Montaigne’s thoughts on debate and Rooney’s contemporary reflections on competitive debate, which concerns their treatment of authenticity. Rooney critiques debate for demanding a kind of performative passion, especially from women, to mask ambition and appear relatable. This expectation distorts the sincerity of engagement, as participants perform conviction rather than embody it. Montaigne, as the quote above underscores, values authenticity as central to meaningful discourse, even though he doesn’t believe any human has a truly authentic nature..

In his view, conversation should be a space where participants feel free to express their thoughts without pretense or fear of judgment. Rooney’s acknowledgment that success in debate often involves projecting a persona contrasts with Montaigne’s aspiration for sincere dialogue. Yet, both agree that intellectual exchange—whether as debate or conversation—has the potential to transcend the boundaries of individual ego and connect people in profound ways, even if those connections are fleeting or imperfect.

As Merleau-Ponty suggests, Montaigne’s essays serve a similar purpose. They are less about providing answers than about engaging in a dialogue with himself. Debate, for Montaigne, is an extension of this dialogue—a means of testing his ideas against the world and, in doing so, deepening his understanding of himself. This humility, the willingness to admit one’s ignorance, is at the heart of Montaigne’s philosophy and his approach to conversation. He would undoubtedly not recognize the activity Rooney participated in and described so vividly.

Montaigne also had very little patience for logicians, a critique that echoes Merleau-Ponty’s rejection of purely abstract reasoning. Both recognize that formal logic, divorced from lived experience, fails to capture the richness of human understanding. For Montaigne, true debate requires passion and immediacy, qualities that Merleau-Ponty identifies as essential to our embodied, emotional engagement with the world.

There is the man who cannot see reason but holds you under siege within a hedge of dialectical conclusions and logical formulae. Who can avoid beginning to distrust our professional skills and doubt whether we can extract from them any solid profit of practical use in life when he reflects on the use we put them to? Such erudition as has no power to heal. Has anyone ever acquired intelligence through logic? Where are her beautiful promises? She teaches neither how to live a better life nor how to argue properly. Is there more of a hotchpotch in the cackle of fishwives than in the public disputations of men who profess logic? I would prefer a son of mine to learn to talk in the tavern rather than in our university yap-shops.

The “no power to heal” line is powerful — it’s misunderstanding between intellectuals and the polity that’s creating greater distance between experts and democratic citizens when greater understanding is necessary. Montaigne held such intellectuals with a special brand of contempt:

I like and honor erudition as much as those who have it. When used properly it is the most noble and powerful acquisition of Man. But in the kind of men (and their number is infinite) who make it the base and foundation of their worth and achievement, who quit their understanding for their memory, hiding behind other men’s shadows, and can do nothing except by book, I loathe (dare I say it?) little more than I loathe stupidity.

We end up debating — if ever — with tight communities of like-minded people. Montaigne senses an element of tyranny in this:

There is always an element of tyrannical bad temper in being unable to tolerate characters different from your own. Secondly, there is in truth no greater silliness, none more enduring, than to be provoked and enraged by the silliness of this world – and there is none more bizarre. For it makes you principally irritated with yourself: that philosopher of old would never have lacked occasion for his tears if he had concentrated on himself.

As mentioned previously, I’m far less concerned than Montaigne about the dangers of rhetorical style. With so many other forms of entertainment competing today, I find it a minor miracle that anyone would choose to listen to a speech anymore. But I agree with Montaigne that we make far too much of what is now called the “sound bite:”

In debates and discussions we should not immediately be impressed by what we take to be a man’s own bons mots. Most men are rich with other men’s abilities. It may well be that such-and-such a man makes a fine remark, a good reply or a pithy saying, advancing it without realizing its power. That we do not grasp everything we borrow can doubtless be proved from my own case. We should not always give way, no matter what beauty or truth it may have. We should either seriously attack it or else, under pretense of not understanding it, retreat a little so as to probe it thoroughly and to discover how it is lodged in its author.

Montaigne raises an important point of humility: debate is always about understanding and the primary subject is always yourself — what you know, feel and believe:

A man of straight and elevated mind who judges surely and soundly employs in all circumstances examples taken from himself as well as from others, and frankly cites himself as witness as well as third parties. We should jump over those plebeian rules of etiquette in favor of truth and freedom. I not only dare to talk about myself but to talk of nothing but myself. I am wandering off the point when I write of anything else, cheating my subject of me.

His examination of the art of conversation, as Merleau-Ponty observes, is a microcosm of his philosophy: an inquiry without discovery, a practice of living within the contradictions of self and world. Through debate, Montaigne exemplifies what Merleau-Ponty calls the “mixture” of soul and body, thought and action. In sparring with others, Montaigne sharpens his understanding, not to achieve definitive answers, but to inhabit more fully the complexity of being human.

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