Sex + Dating

Things You Need to Know Before Dating a Chicagoan

Chicago Cubs fan
Scott Olson/Getty Images News/Getty Images

Dating in Chicago can be intimidating, to say the least -- particularly if you’re not accustomed to the nuances of the Midwestern bachelor/bachelorette. Aside from all of the baggage that comes along with dating in any big city, Chicagoans themselves are a unique breed. Before you start swiping right out of sheer frustration, there’s a few common quirks you should know about us.

Chicago Cubs stadium
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We’re loyal... probably to a fault

Chicagoans tend to be fiercely loyal -- I mean, you're either a Cubs or Sox fan right? While this will generally work in the favor of anyone we date, it can also create some problems. Amy Schumer, who’s dating a Chicagoan, recently discovered this the hard way.

You better like sports -- or at least be good at faking it

First step: pick your baseball team. Many Chicagoans have a hard time trusting anyone that hasn’t claimed a side.

University of Michigan
<a href=";pl=edit-00">Susan Montgomery</a> / <a href=";pl=edit-00"></a>

You’ll probably end up dating someone with an alma mater obsession

Don’t worry, we’ve also questioned why the heck everyone we meet graduated from either University of Michigan or Ohio State.

Get used to our family -- you’ll probably be seeing a lot of them

Although Chicago is a massive city, there’s still a Midwestern streak deep down inside every Chicagoan. No matter how independent our everyday lives are from our family, we’ll still be paying them a visit quite often.

couple in bed on laptop watching movie
El Nariz/Shutterstock

Winter is “Netflix and Chill” season

By the time spring rolls around, we’re so sick of staying indoors that you’ll get MAJOR bonus points for thinking up fun outdoor dates. But seriously, whatever you do, don’t ask us to spend a beautiful summer day indoors.

The worst thing you can do on a first date is put up a front

Chicagoans tend to be no-bullshit, and this attitude carries over into our dating lives. Gentlemen, a 30-minute monologue about your financial success may be appealing to girls in other cities, but it’ll cause our eyes to roll so hard they may actually get caught in the back of our head. Thankfully, since you’re so rich and successful, you’ll be able to pay for our subsequent visit to an ophthalmologist, riiiiight?

We’re still Jenny (or Joe) from the block

Unlike some of the coastal cities, people don’t come to Chicago to reinvent themselves. No matter how much our lives change, most Chicagoans still remain pretty tied to the places (and people) from their past. Ladies, if you’re dating a Chicago-born man, this means that you’ll probably have to accept the fact that his neighborhood friends will call him some weird nickname like “Joey the Schmuck” for the rest of his life. Yes, even at his funeral.

Getting ready for a date? Come as you are.

Unless you’re heading out to a fancy venue, it’s totally acceptable to wear jeans on a date in Chicago. Let’s face it: we’ll never be the fashion capital of the world, but at least we’re comfortable, damn it.

Like it or not, you’ll eventually meet at least one of our exes

Six degrees of separation? NOPE. More like two. You would think in a city of nearly three million people this would be mathematically impossible. Further proof that math is evil.

We’ll never be a size zero, no matter how many yoga classes we attend

And neither will you. Anyway, whatever... we need the extra padding for winter. Having a little junk in the trunk certainly comes in handy when you inevitably slip on one of the city’s many unsalted sidewalks.

We’re secretly kind of traditional when it comes to dating

While most Chicagoans have had their fair share of dating app mishaps, one-night-stands, and ghosting incidents, deep down inside, most of us are still pretty traditional and would love nothing more to meet the wo/man of their dreams outside of Tinder. But maybe in, like, a year or two. OK, five. I mean, definitely sometime after thirty. We’re still having too much fun being single.

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Lisa Chatroop is so bad at being single that she had to Google the difference between swiping right and left on Tinder to complete this post. Read more on or say hi on Twitter: @Chicagoista.