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.