1. That first brutal day of winter, the one where you contemplate quitting your job or quitting school just so you don’t have to go outside. But your moment of weakness passes. So you grab all your winter gear and put on a brave face as the bone-chilling wind hits you mercilessly.
2. Your first real spring or fall run or bike along the lakefront. Especially in the early morning before the sun comes up or in the evening when the sun is about to go down. And it makes you feel like you have no worries left in the world.
3. That first true day of summer where you know the winter and “still winter” (what other places call “spring”) has finally gone and the sun beats down on you, and the air is warm, and you know this might actually last for a while.
4. Playing volleyball on Fullerton, North Avenue, or Montrose beach after drinking a little too much the night before. But then you think, “Wait, college me is still here?” No, college you is long gone but you did have a veteran night.
5. The feeling of wanting to die inside on Michigan Avenue where tourists take up the entire sidewalk, and can never seem to walk at an appropriate pace.
6. The constant anticipation for the health and well-being of D. Rose. (Even if the Bulls are not your #1.)
7. Feeling underwhelmed by every visitor’s desire to go and see The Bean. And the panic that ensues that they might also want to go to Navy Pier.
8. The anxiety of taking the Red Line when there is a sports game and you’re completely surrounded by intoxicated fans. Add extra anxiety points if it’s on a Cubs game day.
9. The intense hatred you’ll have for college students (even if you are college student) when you’re riding the Red line, especially between Fullerton and Jackson.
10. Getting irrationally mad at someone for how little their rent is compared to yours. And genuinely starting to re-evaluate all your life choices for cheaper rent.
11. Bringing friends to Lou Malnati’s for the first time and watching their entire experience of eating pizza change completely. Same goes for Piece Pizza as far as thin crust goes.
12. The shame of being in Belmont after dark whether it’s for Big City Tap, Berlin, or Cheesie’s. Because really, you should have just gone home.
13. The feelings of both judgment and nostalgia every time you see a couple making out on Clark Street’s Northside at 4 a.m.
14. Visiting a friend in a different neighborhood and feeling like you don’t belong. Never mind the fact it might only be 15 minutes away from your neighborhood.
15. Being exasperated at the slowness of the Brown Line whenever you have to ride it. SERIOUSLY WHY IS THE BROWN LINE SO SLOW?
16. Realizing at some point that you’ve got used to the smell of all the L trains. Especially when you’re coming back from out of town and then you think to yourself, “Red line piss smell…I am home.”
17. The cringeworthy feelings that come with being around the New Yorker transplant who finds every reason on earth to compare Chicago to New York. (And and rolling your eyes every time they do.)
18. When you watch someone from the burbs try to claim they are from the city of Chicago. So you just side-eye and let them be.
19. Being in Wrigleyville during a Cubs game, a holiday celebration, or really just being in Wrigleyville in general. It makes you think bad thoughts about people.
20. St. Patrick’s Day. No explanation needed. You really just have to be here.
21. Getting defensive about the city when people try to talk about the South Side and West Side. Like yeah, we’ve got a lot of work to do but please don’t act like you know anything about those parts of the city unless you do.
22. Negotiating how much you really love this city every March when the winter just won’t go away. And your mental health and emotional stability have become questionable.
23. The fuzzy feelings you get when you witness an act of kindness on the L or having the conductor be humorous throughout your ride, or the random strangers that will say hi to you ever so often. And you’re reminded that however tough the city can be, Chicago is undoubtedly one of the friendliest big cities. Period.