Brinda Gupta

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.

Definitely Emma. I can hang with the yuppies, the hipsters, the hippies, the jocks, the nerds, and the rich kids. Emma and I are both kind of like Ferris Bueller in that way.

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.