In honor of my fifth year anniversary in Chicago, I’m taking time to reflect on all of the things I’ve learned in my years here. The first part of the series is here. 

Every new restaurant cannot be the best restaurant ever

Chicago is a food city. It’s also a sports city, the Windy City, and the City of Big Shoulders, but first and foremost, it is a food city. As such, there are new restaurants opening constantly, and anyone with an investor or a trust fund can try their hand at haute cuisine, food trucks, or even open a pretentious little vault that sells doughnuts for the price of ribeyes to people crazy enough to wait in absurd lines for fried dough. Most people in Chicago become foodies by proxy, and if the restaurant name is trendy enough or if it’s situated on a rough corner in a slowly gentrifying neighborhood, it might be billed as “the best restaurant ever” by the people who go there.

Perhaps the City of Big Shoulders is also the City of Gross Hyperbole, but I’ve heard the phrase “best ever” uttered so many times that it doesn’t even register. The true Chicago boulevardier knows he or she has to supply a more thoughtful portrait. If you’re the first person in your group to eat at a new restaurant, it’s your job to be an apostle, spreading the gospel of truffle fries and Scotch eggs to anyone who will listen. When among your peers, you should be armed with strong opinions about the food, and how the food ranks from best restaurant to (former) best restaurant. You also have to know the lineage—Kuma’s had the best burger ever, but then they branched into Lakeview which made it prosaic, and thereby were dethroned by Au Cheval or Three Aces. They too will be ousted by something that opens in the next six months.

Then there are all of the novelty food shops that pop up that you have to feign interest in—shops that make poutine, bars that specialize in brown liquor, hot dog shops, craft tacos, and places that put bacon in everything. Sure enough, as soon as someone says that BlackWoodBushHouse has the BEST biscuits and gravy in the city, your next brunch invitation will take you there. And, of course, if the food is disappointing your host will always take refuge in the bandwagon-jumpers favorite excuse, “Oh, it was much better the first time we came.”

There are good restaurants everywhere in this city. There are restaurants where you can spend your entire paycheck to literally eat the menu because the molecular gastronomy movement allows for it (and it tastes, as you’d expect, terrible) and there are taquerias with $2 tacos better than the ones you’d spend twice as much for at Big Star.  The secret is that a restaurant’s trendiness is seldom synonymous with its level of quality. The wise diner can ignore the hype in favor of those establishments whose qualities suit their individual temperaments. You don’t have to wait in line two hours of a hot dog, unless of course you want to. For me, the lists of bests include anywhere that you a) don’t have to wait in line b) don’t have to listen to the people next to you discuss the litany of problems with their vintage fixed gear and c) allow you to bring your own beer.

Don’t let anyone convince you that you’re less of a Chicagoan for not having tried every new restaurant in the week that it opens. Perhaps in certain circles there are points to be won for knowing someone who can snag you tickets to NEXT or a mixologist who gives you an exclusively heavy pour. What’s really unfortunate are the times that I’ve been surrounded by people simultaneously declaring something “the best” and being nonplussed that you’ve never heard of it, like we’re at Pitchfork talking about indie bands we love.

At best, you’re gullible. At worst, you’re broke.

Find Your Bar, Immediately.

I found my bar after being in the city for less than a month.  On that night, I headed back to the high-rise where my old boots had taken on water, this time in new heels and a suit for grad school orientation. I hated wearing suits, especially the jacket, but the invitation implored us to “dress to impress” which was synonymous for me with “dress in something excruciatingly uncomfortable, lest you be judged.” Even though I started overdressed, I felt the illusion of sophistication ripping away like I had lost a hand of strip poker every time I met a classmate who had roman numerals at the end of their name.

I still had more of a Kentucky twang at that point, which was at times a point of pride, but in rooms of young aristocrats, a point of insecurity. I sat alone in the corner, sipping the juice that I was handed when I walked in, and tapped my pencil on my notebook. I didn’t plan to take any notes, but it at least kept my hands busy, and if anyone made eye contact, I could fly open the cover and bury my nose in it.

The Dean of the University gave a speech, and while she spoke I looked through the “Welcome to Grad School, Don’t Fuck Up” pamphlet we were handed at the same time as the squeezed mystery berries in a Dixie cup. On the inside of the front cover was a letter from the Dean which seemed redundant since she was speaking from behind a podium inches in front of me, but it contained a biography that told me we did our undergrad at the same university. I hadn’t met anyone from Kentucky since relocating, but more importantly, it gave me a talking point with which to introduce myself. It would also prevent me from saying something stupidly awkward like “I EXCITED I AM SCHOOL GRADUATE EDUCATION” which is always the risk when you ask a wallflower to speak to a powerhouse.

When she approached, I shook her hand and said that we attended the same university. While that reference alone would have sufficed, my nerves forced me to throw in a “Go Cards” with the little L hand gesture afterwards (which is an event I’ve often replayed in my head as one of the most embarrassing things I’ve willingly done). Trent Thomas Edwards Rubenstein the Fourth, or whatever his name was, waited with growing jealousy as the dean and I talked about Louisville the city and Louisville the University. She then told me that she was leaving to go to a bar on the Northside and that if I hurried I could meet her and the alumni group to watch the remainder of the basketball game. With the Dean’s blessing, I blew off the rest of orientation and took the train to the bar, limping blocks in my boxy suit and itchy pantyhose. It was the first and only time I’ve chosen to watch a sporting event in stilettos. I was too shy to do much beyond say hello to the dean and her group, but I took a seat at the bar, which was tended by the owner. He’s no mixologist, but generous in pours and conversations.

In the months that followed, I wandered in there frequently enough that they learned my name, my drink, and even which sporting event I’d want to watch even before I could ask. It’s important to have a relationship with a bar as they seem to last longer than ones with people in this city. It’s nice to know there’s a place that can make you dinner, pour you a drink, and provide friendly conversation when being new can make you sometimes struggle to find it elsewhere.