The Best and Worst of Dating in Chicago
What’s the worst date you’ve ever been on? The question might trigger battlefield flashbacks, but on today’s podcast, we’re getting into it. Producer Michelle Navarro hit the streets to see what locals have to say about Chicago’s dating scene — and what advice they have for getting out there ahead of Valentine’s Day. Host Jacoby Cochran and newsletter editor Emmi Mack help break it all down.
Good News: “Jewels of Spring” and “Showers of Flowers”
Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter.
Follow us @citycastchicago
You can also text us or leave a voicemail at: 773 780-0246
Learn more about the sponsors of this Feb. 12 episode:
- Chicago Board of Election Commissioners
- Access Contemporary Music — use promo code PIANO for 20% off
- Window Nation
Become a member of City Cast Chicago.
Interested in advertising with City Cast? Find more info HERE
Subscribe To Our Newsletter

Stay connected to City Cast Chicago and get ready to join the local conversation.
Latest Episodes
Will CPD Ever Actually Investigate ICE? Plus, The Other Washingtons
Earlier this week, a coalition of Chicagoans who allege they were victims of misconduct and violence during Operation Midway Blitz filed...

Why Did Bally’s Pause Hotel Construction? Plus, 24 Hours in Chicago
Over the weekend, Bally’s Casino hit the brakes on all non-gaming construction in protest of Chicago’s forthcoming expansion of video gam...

Let’s Play Chicago Scattergories! Plus, Moving Tips
Back in June, we played a Chicago-themed game of Scattergories during our live taping at Switchyards Chicago. Host Jacoby Cochran compete...

Will Local Grocers Survive SNAP Cuts? Does Chicago Have A City Council Problem?
Today we’re talking about the impact SNAP cuts are having on grocers across Chicago, the relationship between the mayor and alders headin...

‘Your City Could Be Better’: Naked Neighbors, Unwelcome Pets, and Other City Life Dilemmas — Presented By City Cast Chicago
As much as you love Chicago, city living inherently means sharing space and resources with your neighbors, and y’all certainly have compl...

Why Are More Young People Moving to Chicago? Plus, How To Recycle Your Electronics
While cleanup at Grant Park is ongoing following a massive, rain-soaked Lollapalooza, Mayor Johnson called this year’s festival “the prel...

Cook County Ups Healthcare Relief. Plus, Ariana Grande Supports ALMA Chicago
Over 200,000 Cook County residents are at risk of losing their healthcare coverage by 2028. In response, Cook County is planning to spend...

Why It’s Totally Worth Visiting Every Chicago Neighborhood
Today we’re talking with Chicagoans who have made it their mini-mission to visit every community area. And they have all taken very diffe...

School Board Passes Amended Budget. Plus, Vote on Park Improvements
Last week, Chicago’s school board voted 11-7 to pass an amended $10 billion budget. To avoid hundreds of layoffs, the board budgeted for...

New Mayoral Candidates, More Grocery Closures, and Chicago’s Rainy Summer
On Tuesday, candidates hoping to get on February’s ballot were able to start gathering nominating petitions. That includes folks who want...

