Dating in Chicago can be fraught with error, trials and tribulations. Regardless of how hard you try, you can’t help but run into a few characters along the way before you find one good one. It can get tiring to go through the weekly ringer of cocktails and companionship-seeking. At least Chicago has some pretty nice cocktails you can sip along the way. And on that journey, you'll probably find one of these Chicagoans at the opposite end of a table from you, or sitting, smiling right beside you at the bar.
They just got here.
Why else are they on OkCupid? They don’t know anyone or anything about Chicago and are looking for someone to hold their hand, literally. You have to suggest where to go, what to do and what to drink. Every. Single. Time.
This person just never has time because they’re getting some advanced degree that will earn them more money and more debt than you could possibly dream. And because of it, they’re taking their studies more seriously than they’ll ever take you.
Trendy cat lady.
She's got Netflix. She's got a couch. She does lots of cross-stitching. And she owns a cat she’s creepily too in love with and talks to in an itty-bitty baby voice that makes you cringe. She mostly stays home with her cat or (*shudder*) cats, cooking the cat homemade meals, lying with it in bed, going out only when you text. Creepily, she replies seconds after you hit send.
This guy’s first message was so out of left field you just had to respond. Then he actually managed to charm you with some good conversation, and you met up only to learn he’s a professional drinker. He knows the bartender's first name. He tells you the bar is right across the street from his place.
The person who came all the way from the suburbs.
When you ask what neighborhood they live in, their response is “far LOL.” OK. So, you meet up anyway. Then they arrive much later than planned because they got lost. You know, we really hate to beat a dead horse here, but suburbanites co-opting Chicago as their home needs to stop. It's embarrassing for everyone involved.
The person who wants to do more tourist-y shit than you can handle.
The Bean, sure. Yes, yes, the Lincoln Park Zoo has giraffes. The Adler Planetarium is amazing for a date. Once. *sigh* Chicago has some of the world’s best museums, but staring at art and dead stuff can get a little tiresome after the second and third and fourth times.
The person who doesn’t like their food.
They don’t like the food they got and are too Midwest-nice to send it back or order something different, so they just sit across from you watching you slowly fork a delicious meal that you’re too nice to totally wolf down like you really want to and would be able to if they would just…UGH. What's worse: They suggested the place.
The one who only bikes everywhere during every season.
They show up sweaty and smelling like the wind. Which is kind of nice. But then you want to go somewhere after drinks, like, to their place, and they insist on biking because their ride is too dear to leave locked up overnight. Alternatively, you walk home with them too far and their fixed gear pedals routinely, painfully swing into your calves as they walk their beloved steed between the two of you.
The one with the insanely long, elaborate bus commute to your place.
You both live in areas of the city that demand bus transfers…and a train…and another bus. It’s extremely inconvenient, but they are so cute and they make your heart flutter just so, until they don't anymore and the commute becomes too much to bear.
The one who’s so Midwestern it hurts.
They are from Ohio. They work in Indiana. They live just on the edge of a cool neighborhood. Their point of reference is Cleveland. Wherever you take them they do not fail to name-drop said spot’s corollary (best barbecue, best ice cream) in their quaint hometown that you would never go to even if you were paid.
Angry dibs guy.
It snows and the first thing he does is grab a shovel, a large plank of wood and the chairs from the patio. He guards his parking spot as if it contained the crown jewels of Chicago, and he walks past it several times a day to see if the chairs and plank are still safely askew in the snow. Then, one day, they’re gone. And you're scared, very scared.