19 Awkward Situations Every Chicagoan Has Found Themselves in

Published On 06/09/2015 Published On 06/09/2015

Awkward situations are a part of life and much like a passed-out sunburned fan in the Wrigley bleachers, they can’t be avoided. So instead of shying away from them and pretending they don’t exist, here we present 19 of them in all their glory. Thank you, Chicago, for keeping it weird.

Flickr/David Clow

1. Taking your buddy who’s a Sox fan to a Cubs game

And not the cool, laid-back one. The one who delights in heckling Cubs fans and leaves you no choice but to pretend not to know him.

2.  When the UPS guy clearly sees you but you still pretend you’re not home

Just leave the package downstairs sir, thank you very much.

3. Running out of excuses to visit your friends in the suburbs

“Uh, my car got stolen... again.”

4. Trying not to make it obvious that you’re avoiding clipboard people

Of course you always look down at your phone when you walk. It’s not just when people with clipboards enter your peripheral vision. Honest.

5. Running into a friend’s little sister at a music festival

Yes, she’s all grown up and you’re now officially, officially old.

Flickr/gezelle rivera

6. Weiner’s Circle

Every. Single. Time.

7. Running into ANYONE you know at the Admiral

Come here often? Me neither!

8. Saying “Have a great weekend!” to a coworker and then seeing them on the train

Uh, is this part of that great weekend we were just uncomfortably talking about?

9. Being a woman in the Playpen on Lake Michigan

You thought that viral video on catcalling was bad? Clearly, these dudes have never seen real live women before.

Flickr/(vincent desjardins)

10. Pretending not to speak English when tourists ask you to take their photo by the Bean

What is that rectangular device you are holding and pointing at? I’m not familiar with this technology.

11. Being caught in a lie by a Facebook post

Had to miss your friend’s wedding shower because you were out of town? Then why did they just see you in a Facebook post at Do Division?

12. Putting stuff on the seat next to you at O’Hare & pretending someone is sitting there

No one can give you the evil eye as long as you don’t look up. This book just got really interesting.

13. Running into people at Burton Place who seem to know you, but not knowing their names

Ned Ryerson? Is that you?

14. When a buddy's kicked out for sneaking into a venue's VIP area & he wants you to leave too

Excuse me sir, do I know you?

Flickr/cta web

15. Running after the bus and finding out it’s not in service

What, me? I’m just out here for a jog.

16. The post-Halloween/St. Patrick’s/TBOX/most Saturday nights walk of shame

Seeing people on their way to church can’t be a good omen.

17. When the doors on the El shut just as you are about to get on

And everyone inside is staring at you. Bye bye!

18. Most any human contact on the El

Whether it be hand-on-hand,  knee-on-knee, or butt-to-butt, it’s never a good thing.

19. Day drinking for hours then meeting up with people who WEREN’T day drinking for hours

Everyone seems way less fun now. And why are they staring?

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Jay Gentile is a Thrillist contributor and proud day drinker regardless of awkwardness. Follow him @innerviewmag.



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