12 Ways Dating in Chicago Is Different Than Any Other City

People date in every city (wait, they do, right?), this much we know (RIGHT??). But when it comes to dating in Chicago, it’s a whole other ballgame (Cubs or Sox, but it can’t be both, ya hear?). From two degrees of separation to three months of festivals and constant drinking -- crap, we do that all year long -- finding love in the Windy City is just, well, different. Here's how...


1. "Chiberia" can -- and will -- massively affect your dating life. But not always in a bad way.

Let’s be real: between the months of December and March, removing your Snuggie and breaking away from Netflix takes a lot of effort (s/he better be worth it!). Thing is, that sheer and utter laziness also makes this time of year basically a nonstop hookup fest, mostly because everyone would rather, um, "keep each other warm" than go outside and freeze their asses off on a traditional date.


2. No one enters into a relationship during "Summertime Chi"

By the time Memorial Day rolls around, Chicagoans are ready to go hard. Weekends (and hell, even weekdays) are a blur of street festivals, endless parties, day drinking in beer gardens, and partying on Lake Michigan. Needless to say, commitment levels tend to take a nosedive during this time of year.

lake michigan
flickr/Josh Friedman

3. We'll hook up with you for your boat

Scoring someone with a boat so you can go on boating outings is basically everyone’s summer goal.


4. Our fancy Michelin-starred restaurant dates don't cost infinity dollars

Thanks to places like Longman & Eagle, you can get Michelin-starred fare and a $3 Pabst at the same time without pulling out a Benjamin.


5. You kind of have to be from the Midwest to date someone here

If you didn’t go to a Big 10 school or aren’t from somewhere in the Midwest, you’ll probably have a hard time relating to 75% of your Tinder matches.

6. Even with nearly three million residents, there're still only two degrees of separation

You are bound to run into an ex, friend of an ex, relative of the ex... or wife of an ex. You’ll come across them in the most inconvenient places: Tinder, the doctor’s office... or while you’re viewing an apartment. No joke. It happens. A lot.

bag toss
flickr/Greg Walters

7. You can wear yoga pants and a tank top and still be considered "hot"

Despite being a major city, Chicago is still part of the down-to-earth Midwest, which means you might have a better chance in Chicago of meeting your future spouse while playing bags on the sidewalk and drinking wine out of a red plastic Solo cup. While New York is about status and LA is about who you know, Chicago is all about the party.

8. Sports affiliations can make or break a relationship

Cubs or Sox will always come up in conversation, and the wrong answer could basically ruin everything. And if you’re not a sports fan? Well, let’s just say that you may find yourself pretending to care about your significant other’s team every weekend. Or day, depending on how hardcore a fan s/he is.

Kailley Lindman

9. A dive bar is a totally acceptable date venue

That's because we have totally great dive bars in this town.

Flickr/Kevin Zolkiewicz

10. Your date probably won't be picking you up

In Chicago, doing the old-school "guy picks girl up for date" thing doesn’t make any sense. "Hey girl, let me swing by on the 22 bus and scoop you up" totally does.

for rent
flickr/john kannenberg

11. We can actually afford to stay single

Rent in Chicago is pretty darn affordable in comparison to places like New York, DC, and San Francisco. As a result, we're in no rush to shack up with a significant other in the name of saving money.


12. You don't date beyond your neighborhood

"Oh, you live in Lakeview? Huh... I’m in Wicker Park... please don't call me again.” Also: the city/suburb line is not a dating line you cross. Nope.

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Brandy, Gina, Laura, and Lisa are the founders of Chicago-based lifestyle blog Daily Urbanista. Say hi to them on Facebook or Twitter @DailyUrbanista.