Goodbye Chicago: What It's Like To Live In A City You Tried To But Couldn't Love

I stare down at my gut. I’ve gotten fat. A 40-pound marker of the time that has passed since I first moved to Chicago.

It’s one of many ways my body has felt ravaged by this city. There’s the time I nearly died but instead just broke my jaw and lost 2 ½ teeth. Or the time I nearly died but instead just glided off my bike down the S-Curve’s black ice, immersed in the waves of Lake Michigan. Or the time I nearly died when the driver of a Jeep gunned it out of a stop sign on Milwaukee and t-boned me into the air.

It didn’t start off this way. I first moved to Chicago from San Francisco in January 2014, during the height of the Polar Vortex. Chicago seemed like a place so full of hope and promise, and a welcome change from the dissolving free-spirit of San Francisco.

But three some odd years later, my own spirit, just like my body, have come to feel beaten, defeated.

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And now, as I ascend through the air, on a one-way ticket to New York, I can’t help but reflect back on my time in Chicago and wonder: did I do Chicago wrong?

It’s 14 degrees out. I can feel the inside of my nose freeze as one boot clunks in front of the other, snow crunching beneath it. I like the weather. I’ve never lived in snow, and I’m enamored by it. Seasons represent change and progress, and the ever-present 58 degree fog-laden days of San Francisco always felt like being stuck in the limbo of a better day. As cold as this Chicago day was, it meant warmer ones ahead.

I push open the door to the bar, the heat stinging as it meets the cold of my face. I’ve been in Chicago two weeks, and have made a habit of going out to bars in the hopes of meeting other bar-goers, something that was a cornerstone of socializing in San Francisco.

I ask the bartender for a Lagunitas. I’m impressed that the quirky, indie-leaning Bay Area beer has made it this far across the country. Seven dollars. They were four back home, but maybe this was a fluke. Maybe all the promise of exceptionally cheap Chicago living would prove itself true in another bar.

A table of four women sit to my right. Beer in hand, I approach them.

“Hi, so sorry if I’m interrupting. I just moved here from San Franci—”

As the woman nearest me turns her back, she looks up and sees me, then throws up the “peace sign” in my face and turns away, as if to say “talk to the hand.”

A greeting that became all too familiar to me when I tried to meet people at bars.
A greeting that became all too familiar to me when I tried to meet people at bars.

Her friend seated across from her steps in. “You moved from San Francisco? In the dead of winter? WHY?”

It would become obvious in the coming months that moving from San Francisco to Chicago was a huge point of intrigue.

We continue chatting about work and other mundanities that can be fit into a minute of conversation, but her friend to the right has become visibly agitated. She leans over to my new best friend.

“Why are you still talking to him?” she asks, clearly within my earshot.

“I’m being friendly,” she responds. Just then her friend turns to me.

“Just so you know: we’re all TAKEN.”

What did that even mean? We had hardly been talking for 60 seconds, and suddenly our relationship status had become central to my attempt to meet people. It felt like in that instant I was being told that solidified gender dynamics were alive and well in Chicago, and I wondered if Steve Harvey and Men Are From Mars were still things here.

I could’ve walked away. I would indeed later learn that meeting people in bars was not done the same way it was back home. But I like using my words.

“Just so you know, I don’t want to fuck ANY OF YOU,” I snapped back.

She looked aghast. This was not the crestfallen and deferent response she anticipated.

“What??!! Are you saying that you don’t think me and my friends are attractive?” Suddenly her words and assumptions were reflected back at her, and it was no longer acceptable.

I downed my beer and left my glass on their table. Truth is, I would’ve fucked all of them. But that wasn’t the point.

In Chicago, Chicago is at the center of everything. It’s overflowing with pride. Every little detail is grand, and celebrated, as though it’s “only in Chicago.” On one hand the city keeps shouting about its world-class stature, and on the other it can feel feel like you’re stuck in a small town’s local evening news broadcast.

Residents will tell you Chicago’s public transit is amazing. They won’t mention an entirely non-existent east-west L line on the north side, or lack of bus transfers, or lines that don’t run at night, or that if they don’t own a car, the person they’re dating most certainly does. They will tell you no one parties like a Chicagoan. They won’t mention that they constantly refer to themselves as “being a grandma,” who’s early-to-bed most nights of the week.

The disparity of being told one thing and experiencing another wears on you. It’s a bit like hearing about a friend’s significant other and how she’s the most wonderful, and intelligent, and funny, and beautiful, and progressive woman your friend’s ever dated. And you can’t help but wonder where in god’s name your friend is meeting women.

I know I’m being harsh. I also remember last year, when the news screen in my work’s elevator promoted a new “study” conducted by Chicago-based marketing company, Third Coast Digital, that touted that the best beach city in the entire U.S. was, you guessed it: Chicago.

It feels like Chicago is always trying to prove itself in the pantheon of “important” cities. Third Coast? Oy.

And by proxy, it is to be sure. It’s the liberal beacon of the Midwest, and the biggest city in it. And that seems to be the crux of it: compared to everything else around it, it’s big and it’s liberal. But when you’ve lived in a major city outside the Midwest, cities like New York, Los Angeles, San Francisco, Boston, Seattle, Austin, Portland, and New Orleans, Chicago stops seeming all that impressive or “far along.” Politically, it starts to look like a city where government officials align themselves as Democratic by brand association more than policy. It’s a city where being progressive is approached like most things: with Midwestern reserve.

This isn’t a hate letter to Chicago. It’s a “Hey!” letter. A “hey!” to others out there who may be feeling the same discord and isolation I did, where it seems there is no alternative narrative to the Chicago experience.

So to those who are struggling: do know that Chicago is an incredible city in the Midwest. It has arguably the best improv in the country (New York and L.A. being the contenders to argue) and the heartiest standup scene outside those two cities.

But being new to the midwest and making friends here can be a struggle. It’s a big city, and more importantly a very spread out one. Its population density is low for a major city. You can’t always walk to your grocery store. You can’t always walk to a busy strip of bars. And whatever friends you do make, you most probably cannot walk to them. That distance, be it between residential streets and bars, or the actual seating between tables at bars, means meeting people can be hard.

And that comfortable distance can make those who challenge it feel threatening. Being friendly to strangers more often than not means being polite, but not warm and inviting. Most residents were either born in Illinois or one of its neighboring states. For Chicagoans, the familiar is comfortable; siblings and high school classmates become roommates, and Thanksgiving is always a two-hour drive away.

Chicago is family-oriented. There’s a wholesome undercurrent running beneath it, Mike & Molly billboards and all. I want a wife and kids some day, but I also want to do extraordinary things first. Buying a home and getting married are much more in the sights of Chicagoans. And that makes dating hard. It seems like Chicago is a city of serial monogamy, which means any culture centered around being single can feel lacking.

Things take a long time here: be it grocery stores, or public transit, or competent politicians, this city is fighting a war of attrition on its residents, and change can seem to take so long that you’re just beaten into an attitude of “well, that’s the way it’s always been.”

There is incredible food here. But you have to pay for it. Your run-of-the-mill, baseline food can feel like it lacks any nuance. The overriding sentiment around food culture seems to be “the more, the better.” Putting cheese, and bacon, and an egg, and poutine, and fries, and onion rings, and BBQ sauce on everything is considered a culinary feat. Sometimes the terms “foodie cuisine” and “glorified carnival fare” seem interchangeable. Putting corn chips into burger meat is a real thing.

I came to Chicago seeking a better life. And in many respects, I found that. I desperately needed a job, and I found those opportunities extended to me here in ways San Francisco never did. For that, I cannot thank Chicago enough. I built a comfortable life in my time here. And Chicago is an incredible city to do just that: find a way of life that’s comfortable (provided you’re white, of course).

But I've come to realize that there's a difference between being comfortable and being happy, and right now, I am not happy. And I can't think of a bigger risk than not making the necessary changes to pursue that happiness.

As I leave work for the last time, I decide to stop by the Bean. I take a picture with it. This will be good for the article, I think to myself.

I think about how one conveys grievance and struggle without being met with pride and defensiveness. It’s not easy.

Tears start to fill my eyes as I make that last walk towards the L, and I decide to message my ex.

It's like breaking up with a bad girlfriend... but seeing the shit you went through, just the naïveté you entered into it all with almost 4 years ago. It's all overwhelming. I came to this city alone and hopeful, and I'm leaving alone and something much different.

You can’t help but feel a little stupid.

Did I do Chicago wrong? I don’t know. But I know, like an unhealthy relationship, sometimes two people just aren’t meant to be. And so it’s time to go.

I look out the window. We’re making our descent. It’s a gorgeous city. Its skyline and park and river almost seem unreal, images you grew up with only knowing through the confines of a box.

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And as I look from borough to borough, it hits me that this is a city that truly has it all. A city where anything can happen. It’s terrifying. And exhilarating. And it feels right.

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