Why We Keep Looking for Something Better
Chicago is a city full of options. Windy City Singles often confuse possibility with fulfillment.
I’ve lost track of how many times I’ve heard someone say:
“The dating scene in Chicago is terrible.”
Usually they’re sitting across from me with a look of complete certainty.
My single clients and friends are often individuals whom I consider to be successful, thoughtful, attractive, and at least emotionally available enough to know they’d like to be in a relationship with someone special.
And yet, somewhere between the first date, the dating apps, the situationships, the ghosting, and the people who “aren’t looking for anything serious right now,” they’ve arrived at the same conclusion:
“The dating scene in Chicago sucks.”
What’s interesting is that I hear this from everyone.
Men say it.
Women say it.
People in their twenties.
People in their forties.
Heterosexual, gay, or bisexual.
The person who has gone on two dates this year.
And the person who has had 52 first dates before cuffing season begins.
Everyone seems convinced that the problem is everyone else.
And maybe that’s why I’m not entirely convinced that Chicago is the problem.
Because Chicago should be an incredible city for dating.
It’s walkable.
Social.
Filled with interesting people who have such a variety of lived experiences that you are bound to find someone who can relate to you here.
On any given Wednesday summer night, you can take a first date to stroll along the lakefront for a free firework show via Navy Pier. Friday nights across the city is when you will see thousands of people sitting in highly renowned restaurants, packed into bars, or wandering neighborhood street festivals. We have running clubs, tea shops that host karaoke, street art classes, and about any city league sport you can imagine.
Yet many people still describe feeling profoundly alone.
Why?
Over time, I’ve begun to wonder if the problem isn’t a shortage of good people.
Maybe it’s that Chicago singles have become expert modern daters.
We’ve become remarkably skilled at evaluating one another.
A first date ends and the internal review begins.
Did I feel chemistry?
Was the conversation interesting enough?
Am I attracted to them?
Could I do better?
Did they give off the ‘right energy’?
In my sessions with single clients, I often hear some version of:
“He’s really nice. I just don’t feel the spark.”
Or:
“She’s cool, but another woman messaged me on the app and I want to see where that goes.”
Or:
“There wasn’t anything wrong with him. I just wasn’t excited.”
What fascinates me is how quickly these decisions are often made.
More often than not, it’s after a single date!
Occasionally before the appetizer arrives.
Chicagoans have become so efficient at evaluating people that we rarely stop to ask a different question:
What if intimacy develops more slowly than our judgments do?
What if genuine attraction to someone is not just based on how they present themselves during a happy hour drink in the West Loop?
Fifty years ago, many people married someone they met through work, friends, family, or church.
Today, a Chicago single can sit on their couch in Logan Square and evaluate more potential partners in twenty minutes than previous generations met in a year.
That’s an extraordinary amount of choice.
But choice changes the way we relate to people.
It encourages us to look for certainty before we’ve gathered enough information to find it.
Research around providing choices to humans has demonstrated that given too many choices, and we become overwhelmed with decision paralysis.
Speaking with a single colleague yesterday, I learned that he had created a laundry list of requirements for a potential partner: Over 5’10, college degree, makes at least $80K, sarcastic, athletic because I love playing volleyball and going out, uses public transportation because I value the environment, he laughs at my jokes, he compliments my outfits…
As his list continued, my head began to spin.
Single Chicagoans have become so good at assessing compatibility that we've forgotten how to discover another human being.
If this sounds familiar, I’d encourage you to try two experiments.
Experiment A: For the next three dates, stop asking yourself whether you’ve found your person or “enough” attraction to “see where it goes.”
Instead, ask yourself three different questions:
What surprised me about them?
What became more interesting as the conversation unfolded?
What would I want to know if I saw them again?
Notice what’s missing from those questions.
I’m not asking whether they’re your soulmate.
I’m not asking if the chemistry was electric, because 9 times out of 10 chemistry is misleading.
I’m asking whether you remained curious about getting to know them.
Because curiosity and compatibility are not the same thing.
Most people know how to assess compatibility.
Far fewer know how to cultivate curiosity.
Experiment B: Remain open to a 2nd date, even if you didn’t “feel a spark.”
In Modern Dating, first dates are just a snapshot. It’s rare to have a first date over a lengthy dinner. It’s usually a quick coffee or drink or an appetizer after work. First dates are quite literally just a highlight to who that person is. And most people are not truly authentic upon first meeting a stranger.
As a sex therapist, I’ve noticed that the healthiest relationships often don’t begin with certainty. They begin with interest or nervousness around being liked or two individuals who just want to try and have fun together. The only score card to a first date should be two people who want to discover other details about the stranger across from them. So, they agree to plan a 2nd round of discovery.
The goal of a first date isn’t to determine whether you’ve found someone “on your level.”
The goal is to determine whether there’s enough there to learn something new.
And in a city full of people who have become exceptionally skilled at evaluating one another, the most radical thing you can do might be to stop asking whether someone is good enough for a second date and start asking whether you’ve become curious enough to have one.
Intimacy develops slowly. Try not to make up your mind before it even has a chance to arrive.
— Jess
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