Deep Chats with Strangers in Airport Bars

Issue #38 · A front-row seat to the comedic chaos of humanity in transit. Pull up a chair!

Sep 06, 2024

Hi there, I’m Emily! 🙋🏼‍♀️ For those who are new, here’s a quick catch-up:

Five years ago, I packed my life into a suitcase and hit the road, moving to a new city every few months. Now, I write stories about the quirks, chaos and realities of living abroad, intertwined with my attempt to design a happy, meaningful life.

If you enjoy this post, stick around — something big is coming later in 2025!

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September 6, 2024: Hello from the Big Apple! It’s been nearly a year since I’ve been back in the States and the reverse culture shock is hitting hard as expected.

Even though New York is listed as “place of birth” on my passport, it’s never been a city I see myself living long-term — but I love doing short stints here to soak up the electric energy while feeling like a local and a tourist at the same time.

Today I’m publishing a post that I began writing a few weeks ago while I was still in Spain, and I used yesterday’s long travel day as inspiration to get it over the finish line. It’s long, but it’s a fun one. Thanks for reading along!

Deep Chats with Strangers in Airport Bars

Humans are fascinatingly bizarre. When you break it down, we’re really just squishy bundles of nerve endings, former orangutans who now own smartphones, and reality show contestants fueled by existential dread. We act both impulsively and with logical reasoning; we’re habitual yet curious, communal yet territorial. Some of us are good-natured souls full of empathy, while others are downright evil. And at the end of the day, we’re all just acting out in the hopes of receiving a hug.

That’s why people-watching is my favorite sport. And it’s more than just something I enjoy passively — I consider perching myself upon a bench in a high-traffic zone my life’s mission and one true calling. In fact, as we speak, I’m sitting out front of a cute coffeeshop on a busy street corner in Madrid as a nonstop stream of entertainment in the form of raw human behavior passes by.

Most days, I can’t help but wonder: What drives some people to commit random acts of kindness while others act like complete selfish dicks? Why are some people okay with PDA while others cringe at the idea of a public peck on the cheek? Why do some people put on airs in an attempt to seek approval from strangers, while others shamelessly broadcast their domestic spats to a public jury? This woman has passed by five times in both directions, what could she possibly be up to? And why did this man choose to sit on the same bench as me when there are two other perfectly good, wide open benches just a few yards away?! Oh no… oh god… he’s going to strike up a conversation with me, isn’t he?

Now, while observing humans from the safety of the sidelines is my forte, chit-chatting with these same strangers is an entirely different story. I’m happy to extend a routine “buenos días” to a barista or a universal head-nod to a fellow jogger, but beyond micro-pleasantries, I find small talk with strangers hollow and uncomfortable. Admittedly, this is mostly just me projecting as I can be a bit socially awkward when put on the spot, one on one.

Yet there’s one major exception to my anti-small talk stance: As a nervous flier, I usually seek out a pre-flight, nerves-calming, chilled glass of red wine — and without fail, every time I plop down on a barstool at a Vino Volo or a Chili’s Too, I always end up lost in deep conversation with the unfamiliar face sitting next to me.

Quick backstory: I’ve spent the last four years traveling full-time, which means I’ve spent a ton of time in airports, often alone. I’ve come to the conclusion that between the jetlag, the melting pot crowd and the socially acceptable custom of eating Sbarro’s for breakfast, airports are the crown-jewel, Olympic stage, and undisputed Mecca of people-watching. It’s really just one big petri dish of anxiety, as even the newest, most state-of-the-art, calmest terminal food courts with vibey ambient lighting only exist to distract us from thinking about terrorist attacks or that we’re about to be smushed into an aluminum tube next to someone with walking pneumonia for the next six hours. How could people not lose their minds?

Plenty of times, I myself have been the chaotic main character, unintentionally delivering top-notch entertainment in the form of vocally cursing out flight delays or sprawling myself out on the terminal floor for a good night’s sleep. But no shame, because there’s always somebody worse: The guy who hasn’t exercised in a decade but is currently attempting the 200m dash with three suitcases in tow; the disorganized mess in the recombobulation zone hastily stuffing embarrassing toiletries back into a bag that just won’t zip; or my favorite, that one dude who, as he unbuckles his belt at the security checkpoint, habitually pulls down the fly of his jeans next — “hey so uhhh, we have x-ray machines and whatever, so you can actually keep your pants on…”

Can you even imagine mixing a bit of booze into this already wild, wild west of human behavior?

Perhaps that’s why I can’t help myself from diving into conversation with my fellow traveling barflies — the potential for quality content is just too good. Though, it’s not just the alcohol that gets people loose-lipped. In airport bars, there’s an entire concoction of psychological factors at play that cause people to confide in strangers and divulge the juicy stuff (some of these are proven theories, others highly scientific hunches):

Subconscious Safety: Once you’ve finished getting felt up by your assigned TSA agent, a subliminal sense of peace of mind will instead take hold. Yes, we’ve already established that people act bat shit crazy in airports, but still, they are some of the safest public spaces we’ve got. Perhaps this is a uniquely gun-related American phenomenon, or simply a factor of the sheer number of surveillance cameras per square inch. Either way, as a frequent solo female traveler, it's refreshing to be able to let my guard down knowing that the beady-eyed dude across the bar probably isn’t going to follow me out the door with a crowbar.

Incognito Mode: Okay, so there was that one time when a sweet old lady, after two glasses of chardonnay, asked me if I was single and then for my email in order to put me in touch with her grandson (we LOVE a wing-granny) — but generally, the transient nature of airport bar patrons means that there is zero opportunity or expectation to continue the conversation thereafter. One small dash of perceived anonymity, and suddenly the fella next to you is confessing to tax fraud.

FOMA: Not to be confused with fear of missing out, FOMA — or, the fear of masticating alone — is a disorder in which self-conscious humans cannot bear the thought of admitting to the restaurant hostess that they would like a table for one. The good news: Airports offer temporary respite from this chronic condition, as society has deemed it perfectly acceptable to split a family-style-sized fajita platter with your suitcase. The bad news: There’s the unsettling side effect of suddenly being alone with your thoughts that leads these anxious lone wolves to start swapping stories with a random bar mate.

The Tommy Bahama Theory: Think back — have you ever seen a 55-year-old white male in a Hawaiian-print shirt in Logan Airport in the middle of February not blabbering away? Not a chance! Much of the time, people in airports are kicking off their vacations and just in a good ass mood, ready to talk your ear off. And I hate to break it to you, but that first $18 margarita that got him to overshare about his recent trip to the gastroenterologist is only the tip of the iceberg.

Now, while all of the above elements play a part in generating relaxed, free-flowing chit-chat, when it comes to clearing a path towards vulnerability and deep, candid discussion, there’s one ingredient that stands out from the rest:

The Easy Layup Opener: As you pull up a chair in the liminal twilight zone of an airport bar, there’s one clear and obvious conversation starter just begging to be asked by the friendly face seated next to you — “so, where are you headed?”

It’s important to note that as humans, we are wildly unrealistic when envisioning future versions of ourselves. That’s why a future-facing question like “where are you headed” will often elicit a response packed with inflated expectations and romanticized narration. Every un-lived day ahead is still full of possibility, so who wouldn’t fantasize about the best-case scenario? Funnily enough, it’s these same idealistic replies that end up inadvertently revealing our innermost wishes, genuine hopes and unfiltered aspirations — no deep-cutting questions or probing interrogation necessary.

This is why just ten minutes after I ordered a glass of pinot at SFO one time, the woman next to me revealed that she and her new boob job were on their way to Austin to win back her ex. It’s why a gentleman in a suit once confided in me that he was miserable at work and, even though he still hadn’t told his wife, he was planning to quit after this one last business trip. It’s why that single dad I chatted with on a layover at O’Hare told me that he just knew this would be the family vacation that finally ironed out all of the hiccups with his kids.

Call it wishful thinking, but daydreaming about our untapped future potential is much more enjoyable than rehashing the blunt reality of the past — it’s human nature. Let me put it this way: When a coworker asks how your weekend was, sometimes the honest answer is embarrassing! “Well, Deborah, my La-Z-Boy and I morphed into one lifeform, I ordered Domino’s twice and I attempted to disassociate from this hell hole of a job” is not exactly the version of ourselves that we want to put out there for discussion. But talking about our dreams and visions of what one day could be? That’s the good stuff.

So if you’re like me, and have long yearned for a magic solution for what to do when you find yourself yanked from the safety of your people-watching bench and thrown into the uncomfortable cross-fire of small talk, keep this in mind. Rather than mentioning the weather, the score of last night’s Orioles game or asking my biggest pet peeve of a question, “so, where are you from?” instead, consider swapping that out for “so, where are you headed?” Because no matter how the other person chooses to interpret it, by making use of future-facing questions, you’ll bypass any superficial, awkward small talk and instead propel yourself into deeper, more compelling, meatier conversation — no boarding pass required.

Recommended related posts:

The Best Things in My Life are Free — A perfect encapsulation of why I feel such insane culture shock when I come back to the States.
Follow Me to Weird Places — Encouragement to step off the beaten tourist path and get lost in unpronounceable places.