Getting to know people behind the scenes. At most venues, managers, bouncers, servers, and bartenders went out of their way to help me. It was fun to walk into a place with an “in.” Not paying cover and sometimes getting free drinks was nice too!
As a lifelong Chicagoan, I expected Billy Goat Tavern to be a tourist trap. Yes, there were tourists there, but I absolutely loved it. It’s subterranean and gritty, hasn’t been redecorated since mid-century, and was full of cigarette-voiced reporters from the nearby papers and TV stations. So many media legends have used it for their clubhouse, and I felt like I was standing on the shoulders of writing giants. Also, the bartender was from Morocco, which I had just visited, so I had a great time just hanging out at the bar talking to him about it.
The perfect morning would involve a run along the lake or time in the park with my dog, followed by brunch at M. Henry with my best friends. I would love to spend the day exploring a new neighborhood, ducking into stores and cafés. In the evening, drinks at a sunny beer garden with my gang, dinner at one of our favorite BYOB joints, and a nightcap at a wine bar.