Skepticism: A Socratic Dialogue

I want to thank one of my readers, Emily Hess, for her critique of a recent Socratic dialogue I wrote, describing it as “a little soulless.” I love writing both short stories and Socratic dialogues, but I suspect—though I’m not entirely sure—that she meant the interlocutors lacked personality.

In response, I’ve tried blending the two genres: a short story infused with Socratic dialogue. You can let me know if I failed miserably, or not so miserably in the comments below.

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Photo by Rod Long on Unsplash

In the bustling city of Port Athens, tucked between its library and a secondhand vinyl shop, there was a coffee house called The Gadfly. It wasn’t the sort of name you’d expect for a coffee shop, and that might’ve been part of the problem. For all its excellent coffee, warm lighting, and relaxed atmosphere, The Gadfly was often quieter than it should have been. Maybe it was because most people weren’t sure what a “gadfly” even was, or if they did, they weren’t sure they wanted to drink coffee named after it. The regulars, however, had no complaints. It was their little secret, their quiet corner of the world, away from the clamor of the town.

Inside, the café was a mix of cozy and eclectic. The walls were lined with bookshelves, half-filled with mismatched volumes donated over the years. A mural of Modest Mussorgsky, for some unknown reason, painted in earthy tones took up one wall, his wild hair and intense eyes giving the room a dramatic flair. The tables were sturdy, their surfaces worn smooth from years of mugs and conversation, and the air carried the inviting scent of freshly brewed coffee and just-baked muffins. The baristas worked with a casual rhythm, always ready with a smile or a suggestion for indecisive customers.

It was here, at The Gadfly, that Leo showed up like clockwork every morning. He’d been coming for years, longer than even the most seasoned barista could remember. Leo was a man in his thirties with a kind face, framed by dark, slightly unkempt hair that always looked like it was a few weeks overdue for a trim. His beard was short and scruffy, giving him an easy, approachable look. He was never one for dressing up—just a black t-shirt and jeans, every day without fail. Arriving just after the morning rush, a book tucked under one arm with its corners worn soft from years of use, he would make his way to his usual seat by the window, the spot where the light spilled in and offered a perfect view of the lively street outside. Over time, Leo became something of a fixture at The Gadfly, as integral as the tables and chairs themselves. The baristas knew his order by heart—a cappuccino, light on the foam—and they also knew, with absolute clarity, that he wanted cow’s milk. Not hemp milk, almond milk, or whatever freakish liquid someone somewhere had just decided could pass for milk. Leo’s loyalty to dairy was both clear and non-negotiable.

But Leo’s reputation extended beyond predictable order or familiar face. Word had spread about the cheerful man with the well-worn books, the one who could talk about faith, philosophy, or the meaning of life without ever sounding preachy. People said he had a way of answering questions that made you feel like he was learning right along with you. Occasionally, someone who had never even stepped foot in The Gadfly would show up, drawn by what they’d heard about Leo. They didn’t come for the coffee or the pastries—they came for him. Some came for a friendly chat, others for a spirited debate, curious to see if the man lived up to his reputation.

Today, it was Renny.

Renny was a self-declared skeptic, a man with sharp eyes and a thoughtful curiosity that often came across as bluntness. He had heard about Leo and decided to see for himself what all the talk was about. After placing his order—a simple black coffee—Renny approached Leo’s table, asked if he could join him, and sat down. Leo, used to this by now and almost expecting it, welcomed him with the calm demeanor of a man who had grown accustomed to being approached—like someone sitting at a chessboard in Central Park, ready for the next curious challenger.

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Renny: I don’t have much time.

Leo: That’s fine, take a seat.

Renny: Thanks. So they tell me you’re a Christian?

Leo: I am, are you?

Renny: No. I mean, don’t have anything against Christians; just disagree with them, is all.

Leo: Fair enough.

Renny: I don’t understand how people like yourself can be so sure about things. I used to be a Christian. Was raised Catholic. I now think that certainty is an illusion. That we can’t really know anything for sure.

Leo: That’s quite the claim. Do you really think that? That we can’t know anything at all?

Renny: Correct. I think that any belief we hold can be doubted. Including what Descartes said about thought needing a thinker. But, that might be getting too deep too fast. Look at history—people were once so certain about things we now know are wrong. They thought disease was caused by bad air, or that the stars controlled their destiny. How can we trust that we’re any better now?

Leo: That’s true; people have been wrong about a lot of things. It’s good to question and stay humble. But let me ask you this: are you certain that we can’t know anything?

Renny: I see what you’re trying to do.

Leo: What am I trying to do?

Renny: You’re trying to trap me in some logical paradox. Fine—I’ll admit it. I know that we can’t know anything.

Leo: You’re right. I was trying to trap you. Well spotted. And I’m glad you see the contradiction. If you know that we can’t know anything, doesn’t that mean you at least know that?

The barista walked over, balancing a steaming mug of black coffee. She placed it on the table in front of Renny, who nodded in thanks as she headed back to the counter. He picked up the mug, took a long sip, and leaned forward, his brow furrowing deeper.

Renny: That’s just semantics, Leo. What I mean is, any belief can be doubted. There’s no foundation—no rock-solid certainty we can stand on.

Leo: I see. But isn’t the act of doubting itself built on something you’re certain about? For example, when you doubt something, don’t you have to be certain that you’re doubting it?

Renny: Maybe. But even if I’m certain I’m doubting, that doesn’t mean I can trust anything beyond that. Our senses deceive us, our memories are unreliable, and our reasoning is biased. How can we trust anything?

Leo: That’s an interesting point. And forgive me if it feels like I’m trying to trap you again, but isn’t your skepticism itself based on a kind of certainty? You say your senses deceive you—how do you know that unless you’re certain they’ve misled you in the past?

Renny paused, the mug halfway to his lips. He seemed to consider this for a moment before setting it back down.

Renny: I suppose I’m certain that my senses have misled me before. But that doesn’t help your case. It only proves my point. My senses are unreliable, so I can’t trust them now.

Leo: True, but let’s think about what you just said. If you’re certain your senses misled you before, doesn’t that mean you’re relying on your memory of those past mistakes? You’re trusting your memory to say your senses failed you.

Renny: I guess so. But memory can fail too. Just because I think I remember something doesn’t mean it happened that way.

Leo: Granted—memory isn’t perfect. But let’s not go in circles. Your skepticism about memory and senses assumes something deeper, doesn’t it? You trust your reasoning to conclude that they’re unreliable.

Renny: Are you saying I should stop trusting my reasoning too? Because if that is what you’re suggesting, it sounds like you’re actually making my point for me—that we can’t trust anything, not even our own thought process.

Leo: Not at all! I’m saying that even when you doubt, you’re relying on your reasoning to make sense of your doubts. You trust your mind to follow logical steps, even if you question everything else.

The shop door jingled as another customer entered, shaking off rain from a dark coat. Leo glanced at the newcomer and smiled briefly before turning back to Renny, who was staring at his coffee as though it might answer for him.

Renny: So what? Just because I rely on reasoning doesn’t mean it’s reliable. It’s the best tool we have, but even that’s not foolproof.

Leo: Agreed, reasoning isn’t foolproof. But here’s the thing: If you throw out reasoning entirely, you can’t even make your argument for skepticism. Saying “we can’t know anything” depends on reasoning—it’s a conclusion you’ve come to through thought and logic.

Renny: Fine. I rely on reasoning. But that doesn’t mean I can know anything for sure. There’s always the possibility I’m wrong.

Leo: Fair enough. Absolute certainty about everything might not be possible. But does that mean we can’t know anything at all?

Renny: If I can always be wrong, then yes—it means I can’t truly know.

Leo: Let me ask you this, Renny. Do you know that you’re sitting here, in this coffee shop, talking to me?

Renny: I think I am, but I could be dreaming. Or hallucinating. Or in some simulation.

Leo: Maybe. But even if you’re dreaming, aren’t you at least experiencing something? Whether it’s a coffee shop or a dream of a coffee shop, there’s still an experience happening.

Renny: Possibly. That brings us to Descartes, and I don’t know if the self is as we’ve come to understand it. But okay, for the sake of argument, sure, I can know I’m experiencing something. But that’s not much to go on, is it? doesn’t get us very far.

Leo leaned back, sipping his cappuccino, a hint of amusement flickering in his eyes.

Leo: It’s a start, though, isn’t it? From there, we can build. If we can trust some experiences—even just a little—we can begin to test and refine our ideas. Like how scientists build models of the world. They don’t claim perfect certainty, but they make progress.

Renny: And yet, those models are always being overturned. What progress is that?

Leo: Well, I mean, progress isn’t perfection. Just because we refine our understanding doesn’t mean we’re lost. Would you say we know more about the universe now than we did a thousand years ago?

Renny: I suppose. I don’t know. But we’re still working with imperfect tools.

Leo: True. But imperfect tools can still reveal truth. A cracked mirror might distort the image, but it still shows you something real.

Renny stared at Leo for a moment, then glanced at the rain streaking down the window. The shop had grown quieter, with just a handful of customers scattered around, some tapping away at their keyboards, others speaking in low voices.

Renny: So, you’re saying we don’t need absolute certainty to know things?

Leo: Exactly. We don’t need to know everything perfectly to know something truly. Even your skepticism depends on knowing some things—like your certainty that your senses have failed you before.

Renny: Yeah, yeah, I get it.

Leo: Well, something to think about anyway.

Renny: I gotta run. Have work in 10 minutes.