Solo in Chicago: A People Watching Tale

Traveling solo is a funny thing. 

If you make friends, it’s cool. If you don’t, that’s still cool too. 

My actual meal from the Girl and the Goat. Sorry, I was so hungry by this point and it looked so good that I started eating the crab rangoon before I remembered to take a picture of it…

I’m writing this while sitting on a curb in a new pedestrian friendly outdoor eating zone made possible by Covid in between bites of deliciously spicy shrimp salad and sumptuous crab rangoon stuffed in squash blossoms that I picked up from the Girl and the Goat (a dope restaurant by celebrity chef Stephanie Izard if you happen to find yourself in Chicago). 

Not far from where I’m perched is an outdoor impromptu bar area (again: Covid) with groups and couples, friends and families, just hanging out having a good (masked-up) time. To reiterate: I’m here, by myself, eating dinner, watching loads of people maybe 50 feet away from me having a great Saturday night out.

But honestly, the being alone bit doesn’t bother me in the slightest right now because the people watching here is absolutely nothing short of amazing. 

There’s a woman who looks to be about mid-50 dressed up like she’s 25, huffing and puffing and complaining that she can’t order wine to go and must only pick from two delicious cocktails or craft beers (again, by the infamous Stephanie Izard, but this time from the Little Goat Snack Bar). Mind you, there are not one, not two or three, but LOTS of other outdoor bar options to choose from if she really hates it here that much. Funny thing is, it looks like her date chose this place and from the looks of it he is perfectly content with his decision. I’m sure this relationship will go far. 

People watching, for those of you new at the sport, is also a great way to make up crazy outlandish stories about people you don’t even know just based on how they look or what they are doing in front of you at that particular moment. Sounds super judgy? Oh, most definitely. But it’s also for sure a ton of fun.

Then there’s this maybe 30-something guy walking by who looks absolutely miserable. He had a dog leash in one hand with his giant fluff ball (sorry, I’m shitty with dog breeds) and he’s dragging a kid’s tricycle along the pavement in the other. I realize he’s not there alone (just only in his mind…). He’s walking about five paces behind an uptight looking woman pushing a toddler in a baby stroller. She looks like she could absolutely give a fuck that he’s there at all. Another positive relationship sighting in Chicago checked off the list. (Maybe there should be a people watching scavenger hunt game…)

Then there are the Kardashian-wannabe-lookalikes who both confuse and impress me. They are three 40-something women walking around fully done up with fake eyelashes, smoky eyeshadow, and too-dark brown lipstick for the early evening, wearing bandage dresses over voluptuous curves in the sweltering heat. I have literally no idea how they are not melting from wearing all that spandex and how their faces are not perpetually in a state of breaking out from caking on layers and layers of makeup in this humidity. 

There are definitely more people in this area right now that I could be writing out, but these are the ones that I have admittedly been creepily paying the most attention to just out of sheer fascination.