I’m totally pulling a Carrie Bradshaw, minus the cigarette and downtown Manhattan apartment that she was able to afford alongside an expensive shoe addiction. I get it though. We are basically the same, me with my dinky studio in Lincoln Park and my expensive GrubHub addiction.


…where did you get all that money?

As you can glean from the title, what I want to talk about today is inevitably partly autobiographical, but also informed by some wonderful friends.

What does the landscape look like for a single person in Chicago? What are your options to meet people? What will the future hold? I can answer none of these definitively, but will certainly ramble about them here.

Chicago is a wonderful city. It took moving to another city to realize I had taken it for granted. In 2016, Chicago boasted a population of 2.7 million people. 51% of people are women, so you’d think that 49% would make it easy to meet men, right? Wrong!

Even in the last few years, I’ve found it increasingly more difficult to meet men, in real time, online or on the plethora of dating apps that offer their spin on more or less the same concept.

I’m no Bella Hadid, but I consider myself a healthy, modestly attractive, smart person with something to offer. I am baffled by people I know to be fantastic catches that have also struggled to meet people or make any meaningful, romantic connections. Why is it that in a city practically made for dating, given all of the fabulous food, music, art, night life, sports, parks and lake, people are getting frustrated with the dating scene here?

First, I think the means of meeting people has become largely digital. You don’t see people actively trying to chat someone up at the bar or the grocery store anymore, partly because they’re buried in their phone, often in the effort to meet up with someone from online! The problem with this is that it is extremely easy to be flaky, vapid and distant when you can’t see, hear or experience a person.

Let me be clear; I have been of these types of behaviors, most notably “ghosting”. This essentially means that you decided to drop off of the face of the earth and willfully out of someone’s existence without any explanation. This is awful. How do I know? Because it’s happened to me, too. These apps enable rude behavior and don’t exactly encourage serious intent.

So what do you do when you’re sick of the apps and when you go out (rarely, in my case), you don’t find people that seem open to meeting? The truth is that I don’t know.

Is everyone hiding in their house because of the cold weather or the confusing political and social climate? What is happening, Chicago?

From my own reflection on the subject, I’ve come to the conclusion that really the only thing you can do about it is handle your own self. Unless one of the Kardashians create a solution to this problem, one person can’t just alter this dating landscape. So if you’re frustrated, here’s what I think make the most sense for you to do:

  • Do the activities that you like. Whether it’s going to the gym, sitting on a patio with friends, brunching, or doing an art class, do it and enjoy it, but limit the interaction with your phone. Give off positive energy and open body language signals. Again, looking down into your phone will not welcome any person, let alone a potentially interested and cute suitor, to talk to you.


  • Try getting out of your comfort zone. If you normally have people approach you, maybe you try striking up a conversation. Or, maybe you go to a venue like a concert or the beach, where you normally don’t go. The worst thing that can happen is they reject you and you can laugh about it with your friends later, and then cry into your Michael Fassbender body pillow about it when you’re alone.


  • If you feel like trying the dating apps for the first time, or again after furiously deleting them, just remember to keep your expectations to a minimum and to try to hold yourself to the golden rule.


Please remember, I’m not an expert. This is just me sharing some insight with you from the last few years. Hopefully it encourages you to be an engaged, friendly and openminded person that will allow you to enjoy the bounty that Chicago has to offer, get out of your comfort zone and get off your phone for even a minute! And somewhere, my mom is yelling at the screen saying, “You need to work on all of this.”

Thanks, Mom.

One thought on “Single in the Windy City

  1. Mom says:

    You need to work on all of this!!!!!


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