23. Meeting at the Michael Jordan statue
Everyone tries this, now you're stuck in a sea of people and you missed introductions. And that's the best part!
24. Letting your Uber driver stray from GPS
You’re going into the nearest congested six-way intersection.
25. Forgetting gloves
Mom raised you better.
26. Accidentally getting on the Skyway
Time for an impromptu visit to Indiana.
27. Never exploring the city
If you were going to stay within a three-mile radius of your apartment, you should have stayed on your Big-Ten campus.
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Sean Cooley is Thrillist's Chicago Editor and if you break up in his mailroom he might live Tweet it. Follow him @SeanCooley.