The internet handed me a meme a couple of years ago…My response was immediate: Pretty sure the price is your peace and mental health.
That was two years ago. There’s been inflation. The price now includes your peace, your mental health, and several unpaid hours of forensic analysis trying to determine how “let’s see where this goes” can coexist with “I want intimacy”and “I don’t want a label.”
Dating has never been especially consistent for me. I’ve had a man discuss combining finances on the first date while my body was actively rejecting him with hives. Sir, we haven’t even ordered enough drinks for me to entertain this conversation. I’ve had men tell me they loved me before they had even learned my middle name. I once gave a man my phone number and within five messages he had gone from nice to meet you to Fifty Shades of Grey.
But somehow the truly confusing ones are the men who come in interested, make plans, create all kinds of momentum—and then suddenly decide they’d rather “keep things casual.” Somehow, I’m then accused of wanting more than they do.
Sir. Don’t write checks you can’t cash.
I didn’t hallucinate the first half of this interaction. You were participating. I have receipts.
Are all men handed the same playbook at the onset of puberty? Because there seem to be only two chapters. Chapter One: I know we’ve been on one date, but I’ve never felt this way before. Chapter Two: I really like you, but let’s not put pressure on this.
Is there no chapter called: I like you. Let’s keep dating and get to know each other like normal people. No declaration of eternal love before the appetizer. No six-month waiting room where we’re doing everything associated with dating while pretending nobody knows what’s happening.
Just… dating. I think that edition is out of print.
And before this starts to sound like I believe I’m the only reasonable participant in modern dating, I once declined a second date with a perfectly nice man because I couldn’t get past his driving loafers. Nothing was wrong with him. The shoes were just… no.
Meanwhile, I have also dated a man who peed on my floor, so apparently my standards are not always arranged in a logical hierarchy. At this point, I would like to clarify that the bar is not high. It’s dry. No peeing on my floors.
So no one here is claiming moral superiority.
The thing is, men ARE attractive. I’m not blind. I’m just not sure I can afford them.
Dating can require an exhausting amount of interpretation for something involving two adults who theoretically possess language. What did he mean? Why did he say that? Why didn’t he say this? Does “I had a great time” mean I had a great time, or thank you for your participation in this evening’s program?
There is an exhausting amount of literary analysis involved in modern dating.
Meanwhile, something else has been happening.
I’m falling for Chicago.
And Chicago is doing this very differently. Chicago has not tried to convince me that we are soulmates. It has not asked me to define the relationship. Nor has it accused me of moving too fast, or of not being on the same page. It has not made promises about where we’ll be in five years.
It just keeps showing up.
A skyline in my rearview mirror. A train rattling overhead. A neighborhood that makes me immediately want to know who built it, who lived there, and what it looked like a hundred years ago. Something beautiful. Something ridiculous. Something that makes me stop and think: Okay. I really like you.
Men can feel vague. Chicago feels intentional.
Men have stood me up. Chicago never has. It may change the plans, throw me a curveball, send the whole day completely off script.
But it always shows up.
And maybe that’s part of why this city feels so romantic to me. It keeps meeting me with something—a new street, a strange story, a view I wasn’t expecting, a place that makes me curious enough to stop and look twice.
I never feel like I have to audition for Chicago’s attention. I just show up as myself, and somehow the city keeps giving me more to love.
Today, I rode the flying train downtown to find a spot to write about my new love affair. Which, when I think about it, may be one of the more romantic things that has happened to me lately.
Dating sometimes feels like people are trying to skip the part where they actually get curious about each other. They either decide too quickly who you are or spend months avoiding deciding anything at all.
Chicago keeps rewarding my curiosity. I ask one question and somehow end up with five more. I notice something strange and the city hands me something stranger. I leave the house expecting an ordinary day and come home thinking, You are not going to believe what happened.
Chicago has never once made me feel like I’m too much for noticing all of it. If anything, it seems to lean in, almost like it’s amused.
Oh, you liked that? Here. Look at this.
And I do.
That may be what I’m falling for most. Chicago doesn’t seem interested in interviewing me for a role. It isn’t asking whether I’m easy enough, spontaneous enough, low-maintenance enough, or whatever other adjective we’re apparently supposed to advertise on dating profiles.
It just gives me room to be curious, enthusiastic, ridiculous, completely myself. And then it hands me something else to notice.
Men like to keep things ambiguous, leave the door cracked, keep their options open.
Chicago has never once said: “Let’s keep this casual. I’m seeing Milwaukee too.”
Chicago isn’t asking me to define anything. It just keeps showing up and giving me reasons to fall for it.
Maybe that’s the middle ground I’ve been looking for. Not instant certainty. Not indefinite ambiguity. Just interest, curiosity, consistency. Showing up again because there’s still something worth discovering.
I think I fell for Chicago pretty quickly, and I’m still getting to know it. One neighborhood at a time. One train ride at a time. One strange little story at a time.
Men are attractive. Again, I’m not blind.
But lately, Chicago has been making the stronger case.
So for now, I’m dating my new city.
As for men?
Eh. We’ll see.