Closing Time for Bourbon

And why it feels like closing time for everything else, too.

Recently I went to Louisville with a small group for a long weekend. The kind of trip that’s supposed to be about food and drinks and getting out of your normal rhythm for a few days. And it was all of that—great meals, unbelievable bourbon, cocktails that felt more like experiments than something you just order and move on from.

But the moment that stayed with me didn’t happen at a big dinner or during a tasting. It happened in a basement.

We were at Pursuit Spirits, down in their bar before a cocktail class. If you know their story, it makes sense. The brand grew out of the Pursuit podcast—guys sitting around talking bourbon, sharing opinions, going back and forth in a way that always felt more like being invited into a conversation than listening to one. Not polished. Not overly produced. Just knowledgeable, enthusiastic, and open in a way that makes you feel like you’re part of it.

The bar feels exactly like that.

Low ceilings, warm light, nothing overdesigned. The kind of place where the noise settles into a steady hum instead of competing for attention. Conversations overlap. People lean in instead of projecting. It doesn’t feel like a space where you perform. It feels like a space where you’re allowed to just be there.

Our group was sitting together, drinks in hand, somewhere between conversation and that comfortable silence you only get when no one feels the need to fill every gap. At one point, one of the women in our group got up to the bar to grab another round.

But while she was up there, a group of three guys started talking to her—not in a forced way, and not the kind of interaction where anyone was trying to figure the other person out before deciding how to engage. Just conversation. Where are you from. What have you had. What’s worth trying.

A few minutes later, a couple of us drifted up to the bar too. Not as a decision, not as a coordinated move—just naturally, like the conversation had somewhere else it wanted to go. And without anyone really acknowledging it, the line between the two groups disappeared.

We were just there together, leaning on the bar, half-turned toward each other, conversations overlapping in that messy but effortless way where no one needs the spotlight. Someone recommending a pour. Someone else disagreeing. Stories starting mid-sentence like they’d been in progress all along. Jokes landing without explanation. It felt less like meeting new people and more like rejoining something that had already been happening.

And what struck me wasn’t how unusual it was.

It was how familiar it felt.

Like the physical version of that podcast. The same loose, open, back-and-forth energy, just embodied instead of broadcast. No guard. No sense that anyone was managing an impression or trying to be interesting. No invisible calculus running in the background about what to say next or how to position yourself. People were just open in that casual, unforced way that only happens when no one is trying too hard.

At some point, I caught myself thinking—almost without realizing it—that this was how it’s supposed to be, not as some idealized version of life or a nostalgic throwback, but as a kind of baseline for how people naturally interact when nothing is getting in the way.

And what stayed with me wasn’t just how good it felt, but how rare it’s become to experience that kind of ease without needing a reason for it.

Because nothing about that night extended beyond the room. No one exchanged numbers, no one followed each other, no one tried to turn it into anything more than what it already was. It didn’t need to be.

And yet, standing there, part of something that formed and dissolved just as naturally, it was hard not to notice how unusual that has become in the rest of life, where interactions tend to be more guarded, more transactional, more defined by context than by curiosity.

In that basement, none of that seemed to apply. The barriers just weren’t there, and without them, everything else came easily in a way that felt both completely natural and strangely unfamiliar at the same time.

And maybe that’s the point.

Not that bourbon creates something new, but that it makes it easier for something very old to show up again—something simple, something human, something that doesn’t require effort or optimization or intention to justify its existence, just a shared space and a willingness to be in it together.

That’s what bourbon does.

Coming Home

I’ve been to Kentucky quite a few times now, and at some point I realized I wasn’t just going for the bourbon.

I was going because it felt like coming home.

That’s a strange thing to say about a place you don’t live, especially when, on paper, your actual life is stable. I have a house. I have a routine. I live in one of the most important cities in the country, surrounded by smart, ambitious people who are all doing something that matters, or at least feels like it should.

And yet, somewhere along the way—really since leaving Austin—I’ve had this quiet, persistent sense of not quite belonging to where I am.

Not in a way you can point to directly, just a persistent sense that the environment around you doesn’t quite match how you want to exist in it. Conversations feel more guarded. Interactions feel more transactional. There’s always a layer between people, like everyone is running a silent calculation about what something means before they decide how to engage.

You feel it enough times and you start to internalize it. You adjust. You become a little more measured, a little more aware of how things are being received. And over time, that just becomes your baseline, even if some part of you knows it’s not how you’re supposed to move through the world.

So when you drop into a place like that basement in Louisville, and all of that just… disappears, it hits differently.

Because it’s not just that people are friendly. It’s not even that the conversation is good. It’s that the constant calculation just… disappears. You’re not trying to figure out what the interaction is worth or where it might lead or how it fits into anything larger.

You’re just in it.

And when you’ve been living, even subtly, in the opposite of that, it doesn’t just feel enjoyable.

It feels like relief.

Like something in your body unclenches without you realizing it had been tight in the first place. Like you can exhale a little deeper, talk a little more freely, be a little less aware of yourself as you’re doing it—not because you’ve decided to, but because the environment makes it unnecessary to do anything else.

That’s the part you can’t manufacture.

You can’t schedule it. You can’t force it. You can’t recreate it by deciding you’re going to be more open or more social or more intentional about connection.

It either exists in the space, or it doesn’t.

And in a lot of modern life, it just… doesn’t.

Which is why I keep going back.

And it’s not just Louisville.

You see versions of this in other pockets, too, if you know where to look. One of the more surprising ones, at least on paper, is the points and miles community—people who, ostensibly, are there to talk about credit cards, airline programs, and optimization strategies. Not exactly the kind of environment you’d expect to produce anything resembling real connection.

And yet, time after time, those events end the same way.

Not with a formal closing, not with a structured networking session, but with a group of people drifting into a suite somewhere, bottles open, music low enough to talk over, and conversations that start small and then just… keep going.

I saw it again this year at the Chicago Seminars. On the surface, it’s just another gathering—people who mostly know each other from the internet, meeting in person for a few days. But as the night goes on, something shifts. The edges soften. Conversations that would have felt slightly forced earlier in the day start to flow without effort. People move between groups, stories overlap, introductions blur into familiarity.

And suddenly you’re talking to someone you’d never met before like you’ve known them for years.

Not because there’s some shared agenda, not because you’re trying to get something out of the interaction, but because the environment allows it. The alcohol isn’t the point, but it’s the social stimulant that lowers the barrier just enough for everything else to happen.

New friendships form almost accidentally. Not in a dramatic way, not in a way anyone announces or even fully registers in the moment, but in that quiet, unmistakable shift where a stranger becomes someone you recognize the next day, then someone you seek out, then someone who, without much effort, becomes part of your world.

It’s the same pattern.

Different setting, different people, same underlying dynamic.

Not because the bourbon is better—although it is. Not because the food is better—although it’s great. But because for a few days, in a way that feels both effortless and almost accidental, I get to exist in a version of the world where that layer between people isn’t there, where conversations happen without friction, and where being around other people feels energizing instead of something you have to navigate.

When you’ve felt even a quiet version of homelessness—not the physical kind, but the kind where where you are doesn’t quite fit—you start to recognize how valuable that is.

And once you recognize it, you don’t just enjoy it.

You start to need it.

The Table Effect

What happened in that basement isn’t actually mysterious, even if it feels rare.

It’s a dynamic that used to be common enough that no one bothered to name it, because it didn’t need a name. It was just part of how people interacted when they found themselves in the same place at the same time, with nothing particularly forcing the interaction but nothing really preventing it either.

The easiest way to describe it is what I think of as the Table Effect.

Put a group of people in a shared space, give them something to gather around—a table, a bar, a round of drinks—and remove just enough friction that people stop managing themselves.

And once that happens, everything else becomes easier in ways that are hard to fake.

Conversation doesn’t need an entry point. It doesn’t need a reason. It doesn’t need to justify itself. People start talking because they’re there, because something is said, because the moment allows it. You don’t have to earn your way into the interaction or signal that you belong in it.

You just join.

That’s what I felt in Louisville, standing at that bar. Not that people were unusually friendly, but that the environment itself had removed the invisible barriers that usually make interactions feel like something you have to navigate instead of something you can just step into.

And once you start to notice that, you start to see how many of those barriers have quietly become the default everywhere else.

Take coffee shops.

When I was in high school, I used to go to one all the time. It wasn’t anything special on paper—just a local place with mismatched chairs and tables that had seen better days—but it functioned like a living room that happened to serve coffee. People didn’t go there to be alone. They went there to be there. You’d show up and immediately start talking to whoever was around. Conversations bled across tables. Someone would pull out a board game and suddenly five people were playing. You might go with a couple of friends and leave having spent half the night talking to people you didn’t know when you walked in.

It wasn’t remarkable. That was just what it was.

And if you dropped into that same kind of place now—or at least what’s replaced it—the energy is completely different.

People are there, but they’re not there.

Every table is occupied, but every table is its own closed system. Laptops open. Headphones in. Eyes down. The shared space exists physically, but socially it might as well not. The unspoken rule isn’t “join in,” it’s “don’t interrupt.” Even when people are sitting three feet apart, there’s an understanding that you’re not supposed to cross that boundary unless there’s a very specific reason to do it.

The friction isn’t just back.

It’s the entire structure.

And after a while, you stop questioning it. You just assume that’s how it’s supposed to be.

Which is why places like that basement in Louisville feel so different.

Because for a few hours, all of that disappears. The invisible rules loosen just enough that you don’t have to think about them anymore, and once you stop thinking about them, you stop behaving like they exist.

It’s not about the drink.

It’s about what stops getting in the way once people have one.

Not perfectly. Not always. But often enough that it feels like stepping into a different version of reality when you’re in it—and stepping out of one when you leave.

And when that friction disappears, even a little bit, something else comes through that feels both simple and increasingly rare:

People being themselves in the presence of other people without needing a reason to justify it.

That’s the Table Effect.

And once you’ve experienced it—really experienced it, not just as a passing moment—you start to notice how absent it is almost everywhere else, and how much of modern life seems to be structured, intentionally or not, in ways that prevent it from happening at all.

Bourbon Is America

The more I’ve thought about that night—and the feeling underneath it—the harder it is to separate it from something bigger than just a good bar or a well-made drink.

Because bourbon isn’t just something Americans make well.

It’s something Americans are.

Not in a symbolic, flag-waving way, but in the way it developed alongside the country itself, shaped by the same forces, the same tensions, the same push and pull between independence and control that runs through almost every part of our history.

Long before it became a curated experience or a weekend trip, whiskey was a practical necessity. Farmers, especially on the frontier, needed a way to preserve and transport surplus grain. Turning it into whiskey wasn’t just efficient—it was essential. It concentrated value, made it easier to move, easier to trade, easier to store.

It was currency.

But it was also social infrastructure.

Taverns weren’t just places to drink. They were where people gathered, where information spread, where deals were made, where communities—loose and imperfect as they were—actually took shape. In a country that didn’t yet have strong institutions, these were the spaces where interaction happened by default.

You can see that tension show up early, and clearly, in moments like the Whiskey Rebellion, when the federal government tried to tax distilled spirits and frontier farmers pushed back, violently, against what they saw as an overreach. On the surface, it was about taxation. Underneath it, it was about control—who gets to define how people live, how they gather, how they trade.

And that tension never really goes away.

Even at the highest levels, whiskey shows up not just as a drink, but as part of how Americans relate to each other. When George Washington left office, his farewell wasn’t some restrained, ceremonial affair. It was a party. A small group, by modern standards, but the bar tab was legendary—wine, porter, cider, and whiskey flowing freely. Not because it was indulgent for its own sake, but because that was how people marked the moment.

Together. In a shared space. With something that lowered the distance between them.

And that pattern doesn’t stop at the founding.

You see it again in the middle of the 20th century, in a very different version of American life. Offices, restaurants, hotel bars—places where business and social life blurred together, where deals were made over drinks, where relationships formed in the space between meetings rather than inside them. The world captured in Mad Men wasn’t just aesthetic—it reflected a reality where alcohol was embedded in how people interacted, not separated from it.

At the same time, that same dynamic was playing out in a quieter way across the country, in suburban living rooms instead of city bars. The postwar cocktail culture—neighbors dropping by, drinks being poured without much ceremony, evenings that stretched without much structure—was another version of the same thing. Different setting, different tone, but the same underlying function: creating a shared space where people could gather without needing much of a reason.

It wasn’t always healthy. It wasn’t always balanced.

But it was social.

And across all of these eras, the pattern holds.

Alcohol—especially whiskey—has sat comfortably inside American life, woven into how people gather and interact, rarely questioned, rarely separated from the act of being together.

Until, periodically, it is.

The Puritan Cycle + Decline of Drinking

There’s a pattern in American life that tends to reveal itself only when you step back far enough to see more than a single moment.

We don’t really change direction so much as we swing.

Back and forth, over and over again, between expansion and restraint, between letting things exist as they are and deciding that they’ve gone too far and need to be corrected. It’s a rhythm that shows up across politics, culture, economics—almost every domain where human behavior resists clean optimization—and alcohol has always lived directly in the middle of that tension.

Because alcohol is never just about alcohol.

It’s about what people do when they’re together, what they allow themselves to say, how much of themselves they’re willing to show, and how much of that needs to be managed or controlled in order for society to function the way we think it should. Which is why, at regular intervals, it becomes the target of a very familiar argument—that it’s not just a contributor to problems, but the source of them.

And to a certain extent, that argument holds.

There are real costs to excess. There always have been. The instinct to correct for that—to pull back, to impose some level of control, to shape behavior toward something safer and more predictable—is not only understandable, it’s often necessary.

But in the United States, that instinct rarely shows up alone.

It rarely shows up as moderation.

It shows up as moral certainty.

You saw that clearly in the lead-up to Prohibition in the United States, where a coalition of reformers, populist movements, and radical Christian activism didn’t just argue that alcohol caused harm, but that it represented a broader moral failure that needed to be corrected. It wasn’t framed as a tradeoff. It was framed as a solution—one that would restore order, discipline, and virtue to a society that had drifted too far.

And for a moment, they won.

Alcohol disappeared from legal public life. Consumption dropped. Certain harms declined. On paper, it looked like the problem had been solved.

But the underlying behaviors didn’t disappear. The need for gathering, for loosening, for connection in shared space didn’t go away.

It just moved.

Underground. Into speakeasies and back rooms and private spaces where the same dynamics played out, only now without the visibility or structure that had once kept them anchored.

We solved for one set of problems and, in the process, altered the conditions that made something else possible.

What’s striking is how familiar parts of that moment feel now—not in form, but in tone.

What’s different is that the push toward control isn’t coming from one direction.

It’s coming from everywhere.

From the right, you see it framed in moral terms—discipline, restraint, a return to order. From the left, you see it framed in the language of health, safety, and harm reduction. Different vocabulary, same instinct: reduce risk, eliminate uncertainty, make life more controlled.

And this time, they’re not banning alcohol.

They don’t have to.

You can see the outcome in the data. Younger generations are drinking less—meaningfully less. Over the past two decades, the share of young adults who drink has dropped by roughly ten percentage points, and Gen Z now consumes about twenty percent less alcohol than the generations before them. A growing number don’t drink at all.

On paper, it looks like progress.

But every time this country has moved in this direction—every time a coalition of reform, populism, and moral certainty has tried to sand down the messier edges of how people actually live—something else has quietly eroded at the same time.

Because alcohol, particularly in the kinds of settings we’ve been talking about, doesn’t just introduce risk into the system.

It removes friction.

Not all of it, not in a way that eliminates consequence, but just enough that interaction becomes easier, more fluid, less encumbered by the constant self-monitoring that defines so much of modern life.

It creates a kind of ambient permission.

Not to behave recklessly, but to engage without overthinking it. To start a conversation without needing a justification. To stay in it without needing to define what it is or where it’s going.

And when that permission is present, even in small doses, something else tends to follow.

People talk more freely. They linger longer. They become, if only temporarily, less guarded versions of themselves.

The interaction isn’t optimized.

It just happens.

Take that away—or even reduce it enough that it stops being a reliable feature of shared spaces—and the system doesn’t collapse, but it does change.

The spaces remain. The people remain.

But the burden of interaction shifts back onto the individual.

And with it comes a different set of calculations—quieter, more constant, and ultimately more limiting than we tend to acknowledge.

And over time, those small shifts accumulate.

Until something that used to feel natural starts to feel rare.

And something that used to be rare—distance, hesitation, isolation—starts to feel like the baseline.

Dating, Sex, and the Disappearance of Collision

Once you start looking at it this way, a lot of things that seem unrelated begin to line up in ways that are hard to ignore.

One of the most talked-about trends over the past decade is the steady decline in dating, relationships, and sex—especially among younger generations. There are entire industries now built around analyzing it, explaining it, trying to diagnose what’s gone wrong. Is it technology? Is it anxiety? Is it changing norms, shifting expectations, economic pressure, overwork, too many options, not enough options?

All of those explanations carry some weight.

But they all tend to start in the middle of the story.

Because before any of that—before apps, expectations, or compatibility—people have to meet.

Not through a system. Not through a profile. Not through something pre-structured that already defines what the interaction is supposed to be. They have to collide—unexpectedly, casually, in a way that allows for the kind of low-stakes interaction that can either go somewhere or not, without needing to be defined in advance.

That used to happen all the time.

Not because people were better at dating, or more confident, or less complicated, but because the environments they moved through made those collisions inevitable. Bars, parties, shared social spaces where interaction wasn’t just allowed, it was assumed. You didn’t need a reason to start talking to someone.

The setting was the reason.

And when you combine that with what we’ve been talking about—the removal of friction, the lowering of the guard, the ambient permission to engage without overthinking it—you get something that’s incredibly difficult to manufacture intentionally.

You get chemistry.

Not guaranteed. Not universal. But possible in a way that doesn’t require planning or optimization or a clear outcome in mind. It emerges from the interaction itself, from the unpredictability of it, from the fact that neither person is fully in control of how it unfolds.

Take that away—or even just make it less common—and everything downstream starts to shift.

The first conversation becomes harder. The stakes feel higher. The interaction becomes more deliberate, more aware of itself. Instead of something that unfolds naturally, it becomes something you initiate, manage, and evaluate in real time.

Which is exactly what modern dating feels like.

Not because people want it to, but because the environments that once made it easier no longer exist in the same way. So we replace them with systems—apps, profiles, structured interactions that attempt to replicate the outcome without replicating the conditions that made the outcome possible in the first place.

And sometimes they work.

But they don’t feel the same.

Because they can’t.

There’s no shared space. No ambient energy. No sense of being part of something slightly bigger than the two people involved. Just two individuals placed into a conversation that both know has a defined purpose from the start.

It’s efficient.

It’s intentional.

And it’s missing something.

Which is why the decline in sex and relationships shouldn’t feel like a mystery.

It’s not that people suddenly stopped wanting connection.

It’s that we removed so many of the environments where connection begins—and replaced them with ones that are better at filtering than they are at generating anything new.

We didn’t just make dating harder.

We made it harder to run into each other.

Alcohol didn’t create those connections.

But it made them easier.

It created the conditions where people could approach each other without overthinking it, where conversation could start without needing to justify itself, where attraction could build in the space between two people who hadn’t planned to meet but found themselves in the same place anyway.

And without that kind of collision—unstructured, imperfect, a little messy by design—everything else starts to feel harder, more forced, more fragile.

Not because people have changed all that much.

But because the way they come into contact with each other has.

The Tradeoff + Return to Louisville

None of this is an argument for excess.

It’s not hard to see the downsides of alcohol, both at the individual level and at scale. Anyone who’s spent enough time around it has seen where it can go wrong—how quickly something social can turn into something destructive, how easily moderation can slip into something else entirely. The push toward healthier habits, toward more awareness, toward a more intentional relationship with what we consume is, in many ways, a necessary correction.

There are problems worth solving.

The question is whether we’ve been precise about which problems we’re actually solving—and which ones we’re creating in the process.

Because what’s striking about the current shift isn’t just that people are drinking less. It’s that we’ve quietly started to reorganize social life around the assumption that the best version of ourselves is the one that minimizes risk as much as possible, that reduces friction wherever we can find it, that replaces unstructured interaction with something more controlled, more predictable, more efficient.

And in doing that, we’ve solved for a certain kind of clarity.

Cleaner habits. Fewer unknowns. More control over how we spend our time and energy. A version of life that is, on paper, easier to manage and easier to defend.

But the tradeoff doesn’t show up as a problem.

It shows up as an absence.

The absence of moments where interaction doesn’t need a reason. Where you don’t have to decide to be social, or intentional, or open, because the environment itself makes those things the default. The absence of spaces where people collide without planning to, where conversation emerges instead of being initiated, where connection happens without needing to be optimized.

And when those moments become less common, something else shifts with them.

Being around other people starts to feel more like something you manage than something you experience. Conversations carry more weight. Interactions feel more deliberate. The ease that once sat underneath it all—the sense that you could step into a room and simply be with people without thinking too much about how or why—starts to feel less like a baseline and more like something you occasionally get back, if you’re lucky.

Which is why that basement in Louisville stayed with me.

Not because it was exceptional, but because it wasn’t.

Because for a few hours, nothing needed to be managed. No one was optimizing anything. No one was performing. No one was trying to turn the interaction into something else or extend it beyond what it was. People talked, drifted in and out of conversations, shared space in a way that felt easy and unforced and, more than anything else, familiar.

It felt like something I recognized, even if I hadn’t experienced it that cleanly in a long time.

And that’s the part that’s hard to ignore once you notice it.

Not that bourbon creates something special, or even that it’s necessary, but that it still—at least in certain places, under the right conditions—makes it easier for something very basic to happen.

Just people, in the same place, at the same time, with enough space between them to let something unfold.

And maybe that’s the real tradeoff.

The tradeoff isn’t drinking versus not drinking.

It’s friction versus control.

Messiness versus optimization.

A life where connection happens because the conditions allow it, versus one where it only happens when you decide, in advance, to make it happen.

For a few hours in a basement in Louisville, that decision wasn’t necessary.

And standing there, part of something that formed and dissolved just as naturally, it was hard not to feel like I had stepped, briefly, back into something that used to be more common—something that still exists, but only in pockets, only under the right conditions, only when enough of the barriers fall away at the same time.

Not a different world.

Just a different version of this one.

And for me, at least, one that still feels like home.

—David