The Best and Worst of Dating in Chicago
12 February 2026

The Best and Worst of Dating in Chicago

City Cast Chicago

About
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. 

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