06/12/2012 09:36 pm ET Updated Aug 12, 2012

How to Fall in Love With Chicago

Foreword: On my last post on "Reasons I Love Being a Chicagoan," I noticed that not everyone shared my love of the Windy City. For these people (and those who love the land of Oprah and Ebert every day), I thought I would give you a guide to how to love Chicago. Remember: Loving stubbornly and foolishly is what makes us Chicagoans.

You will move here and not know anyone. Everything will look big to you, even the vomit on the sidewalk will look bigger than any vomit you've ever seen. You will be overeager and talk to almost everyone you see and that might not ever stop. It will one day get to the point where you know the names, middle names and life stories of almost everyone you see every day. You will give at least three of your baristas semi-daily relationship advice and will convince one to break up with the long-term boyfriend she was still with -- because you both knew, deep down, he wasn't the one. Like your barista, you will fall in love with almost everyone and everything you see, even the bad stuff and the stuff that hurts. You will even love the Bulls, no matter how many times Derrick Rose gets hurt, because that's what love is.

You will make a bunch of friends almost instantly when you first move here, and you will eventually not talk to almost any of those friends anymore. You will actively avoid at least one of them and recently hid behind a garbage can when you saw that friend walking with her boyfriend down Clark and you weren't dressed for that interaction. You will make new friends that will adorably pester you with their life problems at three in the morning in text messages composed in all capital letters. You will tell them that, yes, they should give their number to that guy at Bangers and Lace, it's OK that they are drunk and, no, they didn't wake you up. You will get drunk with those friends at the Long Room, Late Bar, the Blue Agave, the bathroom of Chipotle or at a Korean karaoke bar and, while drunk, plan to start a metal band so Kuma's Corner can name a burger after it. You will get more drunk when things don't work out like you all thought they would, knowing that life will someday work out better than the life you had planned on.

You will get at least one haircut at Barbara and Barbara you will not understand when you are old, change majors or universities at least twice, dye your hair at least three awful colors in your bathroom sink and date an incalculable number of people who weren't right for you. You will later run into those people everywhere, especially if you are in Boystown. You will stay up way past your bedtime at the Pick Me Up Café, Heartland Café, Nookie's or Taco Burrito Palace with these incorrect people, talking about the future. You will then break up with them somewhere in Evanston, at Ipsento or at the Athenian Room -- because you were already planning on getting Greek food anyway. You will split a side of Spanakopita, some chicken and fries and mutually agree that it's best to see other people. You will see those other people on Plenty of Fish, Grindr or Scruff at least once, and you will probably decide that is not for you. You will definitely decide that is not for you.

You will go home with at least one bartender and flirt with many more. You will not even care that maybe they aren't that into you because it's their job to flirt -- because like Fun. said: we are young. Many of these bartenders will work at the Empty Bottle, Berlin, The Whistler and Big Chicks. If one of them works at John Barleycorn, your friends will never let you hear the end of it. You will make a lot of stupid decisions with a lot of stupid people, especially if you are in your twenties. You make many of these decisions at house parties in Logan Square, Bridgeport or Bronzeville and at downtown bars you didn't know existed. Many of these decisions also will end up tagged on Facebook. You will eat a whole lot of great hangover food in Pilsen, Greektown and at the Lincoln-themed restaurant in North Center that has little to do with Lincoln. You will throw up at least once in Chinatown. You will work in a lot of places you hate, and many of those will be in Lincoln Park or Roscoe Village. They will serve brunch, which will make you slightly resent brunch -- but only slightly.

You will lament the closing of all the good coffee shops and thrift stores in your area and will wear black that time that Earwax closes. You will disregard all pernicious rumors that Wormhole is closing. You will not recognize the fact that Land of the Lost or the Buffalo Exchange in your neighborhood closed, because if a thrift store closes and you don't hear it, that means you can still get discount Marc Jacobs, right? You will not be right. Instead, you will go to Unique or the Brown Elephant and really, really try to find something -- because your friends swear by them -- but will just go to Top Shop and lie that you got it vintage or on sale. You will come to live at Top Shop and will be much poorer because of it. You will also live at Trader Joe's and Stanley's, because Stanley's has the best chips, although you will unfortunately never meet Stanley. You will never have enough money to live at Whole Foods.

You will get at least one terrible apartment and if you are the author, this apartment will be sandwiched between a halfway house and a gay meth den or at the butt of Wrigley Field. You will fantasize about the old apartment you used to have but couldn't really afford and will forget about the ways that apartment made you miserable, too. You will move at least three times and all of those apartments will be within a five-block radius of each other. You will swear that you are a North Sider, West Sider or South Sider for life -- at least until you find cheaper rent elsewhere or your up-and-coming neighborhood gets a Wal-Mart Express, Urban Outfitters or twenty million Starbucks. You will never know what the correct plural of Starbucks is. You will then claim to disavow all knowledge of this neighborhood and contribute to the gentrification of another neighborhood. Some of your friends will take this opportunity move to Hyde Park, West Rogers Park or Naperville. You will never see these friends again.

You will always make plans to go to Wilmette, just to see what happens there. You want to go see the Ba'hai Temple and the Home Alone house, so you can reminisce about your childhood in the comfort of your own car or your friend's car. You will never end up going to Wilmette. You will also live here for a great chunk of your life or all of your life and weirdly have never been to many important Chicago landmarks and cultural attractions -- like the Shedd Aquarium, the Frank Lloyd Wright House, the Oriental Museum or that place where Al Capone ate that one time. You will never get used to the creepy fountain in Millenium Park or look up Marilyn Monroe's skirt, no matter how tempting it seems.

You will see Rahm Emanuel everywhere, so often that you feel like Rahm might be stalking you or Black Swan-ing you. You will then see him at a screening of Black Swan and know he is Black Swan-ing you. You will hope that you see Roger Ebert somewhere, just hanging out and being Roger Ebert. You will never see Roger Ebert, even though he doesn't live that far away from you. You will instead stalk Roger Ebert on Twitter and read him complaining about noise in the neighborhood. You will realize that might be about you. You will not feel that badly about it, because now he at least knows you exist, and your life is a little more complete.

You will spend at least 30 minutes every day waiting on CTA transportation to arrive when it said it was supposed to or waiting for your train not to be on fire anymore. You will spend this time playing Words With Friends, hate reading 50 Shades of Grey or listening to random strangers talk at you. Yes, those strangers will be drunk. No, you will not understand a word of what they are telling you. You will start biking everywhere -- because your hipster friends are right and it really is quicker -- and you will close your eyes for just a second while biking down Lake Michigan on a late summer night and everything will be perfect.

You will tell people you could never imagine living anywhere else, but then it's June and Rib Fest happens and shuts down your bus line for a weekend. And then you will go to Midsommerfest when the weather feels like Africa mixed with a wet nap and you will tell everyone around you will gladly move anywhere else. You will go home and look at apartments in other cities for a bit but then you will go back outside and walk around. The sun will be setting and it will already be 30 degrees cooler. You will run into at least five people you know. You will always be running into at least five people you know, because everyone weirdly knows each other in Chicago. And you will look at them and at the city around you. Everything will still look big to you. Everything will not be perfect, but that's what love is.