Chicago, You’re Gorgeous—But Where’s the Mingle?

I came to Chicago for a girls “treat yourself” weekend—two dear friends, one single me, and a mutual mission: find a kind human who can keep up with my banter and my bike. After a blissful reset at the St. Regis Spa (12,000 square feet of ooh-la-la with skyline views and, yes, a champagne moment if you’re inclined), we slipped into dresses, lipstick, and a little main-character energy. 

And then…we hit the bars.

Here’s the thing no one tells you when you pack heels and hope: so many places now feel like restaurants with a louder soundtrack. Host stands. Assigned seats. “Your server will take it from here.” At one spot, I actually got up to order—flirt-adjacent, conversation-possible, classic city move—and was redirected right back to my table like a naughty schoolgirl with a Negroni habit. Chicago, you have range and beauty for days, but where did the wandering go? The shoulder-bump “oh sorry” that turns into “where are you from?” The bar line that doubles as fate’s waiting room?

In the early 2000s—cue the Carrie Bradshaw voiceover—I remember nights that were basically scavenger hunts for serendipity. You went out not for a reservation, but for a story. Now, I can’t help wondering: when we seated everything, did we also seat our chances? (Somewhere, Carrie is polishing an opening sentence while Gen Z rolls their eyes—and I love them for it.)

Before Chicago cancels me, let me say this: we still had a blast. There were sparks—quick smiles, a few good chats, a bartender who snuck us a tip about a livelier room down the block. But my takeaway was less “wrong city” and more “different game.” If the tables are bolted down, then the move is to pick venues built for flow—standing-room cocktail bars, live-music floors, places where the path to your drink isn’t a straight line; it’s an obstacle course with meet-cute potential. (Salt Shed, I’m looking at your GA nights.)

And because I’m me, the epiphany naturally circled back to IRL Singles Club. I didn’t build this thing because I hate romance; I built it because I love people. Real people. Real life. Real love. The app is free, and the whole point is to get you out doing the things you already adore—in rooms that actually let you roam, laugh, and bump into possibility.

Did I meet The One last night? TBD. Did I feel like the best version of myself with two wing-women in a city that glitters? Absolutely. And just like that, I remembered: sometimes the story is the warm-up. The next chapter starts where the chairs aren’t nailed down.

The only app that gets you off your phone & back to reality.