This story has three players: Ernest Hemingway, St. Petersburg, and an American in Russia for the first time. We’ll call him Chad. This story doesn’t end well for Chad.

Hemingway Bar is located on Ulitsa Lomonsova, a dark and eerily silent street in the lively city center. The bar in question is surrounded by abandoned buildings and telling foreclosures slapped with bulletins in intimidating Cyrillic lettering. But the place lights up at night. It lights up and its emanating glow attracts all those moths looking for a drink.

Sadly, it’s not quite the place Hemingway would frequent; the neon lights and bad music tell me so. My favorite bars are the ones where I can picture the man himself in the corner enveloped by a haze of cigar smoke, drinking scotch, neat, and staring at a pretty girl across the way with squinted eyes and his head to the sky.

Hemingway was the man who taught me to read between the lines, to imagine what the rest of the iceberg looks like even though its majority is hidden, unstated, not there. I step into the bar and Hemingway’s shortest story comes to mind: “For sale: baby shoes. Never worn.” Those seeking drama, impact, or realism are surely quick to assume the baby is dead and the parents are looking to relieve themselves of a useless item that is reminiscent of untimely tragedy (these thinkers are a boring, depressing lot, no?). But I prefer to think that the shoes simply don’t fit. Or they’re an ugly baby shower present. And with a twist, apparent heartbreak transforms into an innocuously erroneous gift or purchase. Hemingway had that gift; the gift of setting your mind off only with kernels of ideas, seeds of minimalism and simplicity that always amount to something much greater and profound. Unnecessary complexity and detail is where strong writing dies (happily, my other modern literary heroes (Orwell, Vonnegut, Bryson) would all toast to this notion).

 * * * *

Hemingway would be able to help the contemporary antihero of this tale, Chad the American. Chad is a lanky insurance salesman from St. Louis, Missouri, a city that he seldom leaves. He works hard and honestly. His credit score is tiptop. He enjoys Italian food and spending time with Herb, his pet turtle. For a rush, Chad occasionally partakes in the lotto. Chad is content, but not happy. Chad is comfortable, but his most insightful thought goes no further than seeing that there is little to gain from incessant comfort.

Because deep down, Chad the American has Romantic ambitions of travel, namely around Western Europe. He wants to dance the night away with Spanish women donning flowers in their hair. He wants to try snails in Paris and have baguette-sword fights on the Champ de Mars with good-looking Parisians. He wants to drink beer in Munich. Chad doesn’t drink too much at home, you see. Herb wouldn’t approve.

To assist the realization of these dreams in the most miniscule way possible, Chad signs himself up for Expedia updates. These emails provide him with optimistic travel tips and flight info so that his trip doesn’t dig too much into the retirement fund. Chad is twenty-six years old.

During work one day, Chad sees an email from Expedia entitled: “Discover Venice of the North: 1-Week All Inclusive Stay in St. Petersburg, Russia” The pricing is reasonable given the luxurious hotel, meals, and excursions. Overall much cheaper than France or Spain, Chad calculates. He is intrigued and immediately bookmarks the email.

Eventually, and due to events that aren’t relevant, Chad decides to set off for St. Petersburg, Russia, Venice of the North, formally known as Leningrad, formally formally known as Petrograd. It will be his first international experience. Chad is nervous, but relieved to be doing something beyond eating Italian food and watching an attractive woman announce the lotto numbers. He promptly arranges accommodation for Herb, much to Herb’s dismay.

Chad does some light research. He is delighted to ascertain that Petersburg is Russia’s cultural capital and Peter the Great’s honest attempt at modernity, style, and the wonders of Western civilization. He respects the Russians for trying to better themselves. He is enlightened by Lonely Planet’s dramatic and memorable description: “Petersburg may be in Russia, but it is not Russian.” What a relief! Chad the American had heard nasty things about the Russian people and culture, things that are not so nice to democracy-loving American ears. And here, it seems, Chad can have it all: a touch of Eastern exoticism but with all the loveliness and ease of Western Europe. St. Petersburg is not really Russia, after all. If Lonely Planet says so, it must be true.

The time comes for Chad to set off, and so he leaves St. Louis and Herb for seven full days in Russia’s Window to the West.

While in St. Petersburg, Chad quickly becomes miserable. He misses his content-but-not–happy equilibrium. It was so familiar, that feeling, and now everything is so unfamiliar. He despises everything about the city. He feels unsafe during the day and night. He is swindled out of his money. People know by his fanny pack that he is American and he is constantly begged and bothered and targeted. Chad doesn’t understand Russian people and their culture and he has no desire to understand them. They’re rude and abrasive. They’re simply wrong. Backwards. Fucked up. Everyone is a thief, an alcoholic, or a prostitute (that’d be a fun Venn diagram). No shred of decency to be found. Chad wants to go home. Herb was right. He never should have left St. Louis. On a lonely walk around the city center, Chad the American sullenly looks to the Neva. He shivers in the wind and turns back.

On his last night, Chad sits at the hotel bar. Another American, an expat, initiates a conversation, and somehow they end up discussing Hemingway’s shortest story ever.

“It goes like this: ‘for sale: baby shoes, never worn.’” Says the American while cradling his whiskey. The ice clinks together.

“It’s terrible that Hemingway killed a baby,” Chad despondently replies.

The next morning, Chad the American leaves the country feeling more alone than ever, all the while unaware that he is not the first American to leave Russia feeling rotten.

He never leaves the States again. Herb is okay with this.

* * * *

Hemingway would have liked Peter because he understands icebergs. To comfortably exist in Russia, you have to abandon all perceived notions of ‘correctness’ and facades and realize what you see and experience isn’t necessarily true. Foreigners are enamored by the shiny perception of it all. Cultural capital! Venice of the North! Window to the West! I would agree with the “window” description. Because while you’re looking at the West, you’re looking at the pretty buildings and canals, you’re actually standing somewhere else far away, like Rapunzel in her tower waiting for her freedom and her prince. Because the Russian mind is not a Western mind. And wherever you are in the world, you’re subject to the whims of a collective cultural mentality, and not the way a place seems to be, ought to be, or is nominally so.

Its essence underneath the brick, Petersburg is more dangerous than Moscow. In Moscow, any person of reasonable intellect is immediately hit with an unease known as “This is Russia”, and they act accordingly. It’s in the air; you simply breathe it and you’re acutely aware of your surroundings. Petersburg is a sneak, a liar, and a trap. It’s a city veiled by European architecture and Venetian canals – don’t be fooled! Don’t mistake this city for Paris and float along the waterways listless and in love with the beauty and White Nights and whatever the place seems to be. Don’t make it what you want it to be. Because while Petersburg may not be Russian, it is still in Russia, and to forget this would be a serious mistake. “Watch your pockets, watch your mouth, and watch yourself”, someone once told me, “or you’ll be brutally reminded that you’re not in a place that makes any kind of sense.”

Spend enough time here, and St. Petersburg will reveal itself to be beautiful and complex in mentality and atmosphere. But I suppose disregarding facades and superficialities goes beyond Russia and extends to every other topic and thing and person and country in existence. There’s value in digging deep, pondering, analyzing, wondering, even though there’s always the possibility you won’t be closer to any kind of truth. To examine is to live. To be content with shells is death long before you’ve died.

Chad has a lot to learn from Hemingway, Petersburg, and even the ice in the Neva. Wouldn’t it be pretty to think that he can one day change? I personally have no hope for him. Because Chad doesn’t travel, which makes him simply, tragically, flawed, of course.