Making same-day plans with people in Chicago?
I moved to Chicago a few months ago and have been trying to meet people / build a social life (mix of Bumble BFF, random events, etc).
Something I started noticing is that the best hangouts I’ve had here were completely unplanned. Like same-day, “what are you doing right now” type of plans.
So I started paying attention and kind of unintentionally ran a little experiment across a few different groups:
Group 1 (met at a park cleanup event):
We barely knew each other, but after the event we made spontaneous plans to grab coffee + walk around. Since then we’ve hung out 4+ times, mostly same-day plans or quick “anyone free?” texts. Super easy, very low friction.
Group 2 (met at brunch):
We all got along really well, made a group chat, etc. But every time I tried to do something spontaneous (happy hour, aquarium day, etc), it just… didn’t happen. People were busy, timing didn’t work, responses came hours later. No one’s fault, just never materialized.
Group 3 (just one person I met in my building):
We planned one thing in advance, but everything after that was super last-minute. He texted me about a farmers market, I said yes, plans changed, we pivoted to coffee + the beach. Ended up being one of the better days I’ve had here.
What I’m noticing:
It feels like people want to hang out and be social, but the more planning involved, the less likely it actually happens.
The “we should hang soon” energy vs “I’m outside, come down” energy are completely different outcomes.
Curious if other people in Chicago feel this too?
Do you actually hang out more when things are spontaneous, or do you prefer planning everything out?