Yes, we’re talking about blind dates here. But thanks to the internet, going on a date with someone you’ve never met before isn’t a novelty. It’s just called dating. Still, it requires some planning. You need a place that’s quiet enough for a conversation, but also interesting enough that you can smile and say “cool place” whenever there’s an awkward silence. It should be easy to bail after half a glass of wine if necessary, but equally easy to share some food and hang out for a few hours when you discover that you both write Harry Potter fan fiction and have a closet full of Slytherin robes. These 12 bars and restaurants will get the job done.
You can’t go wrong with The Delta in Wicker Park, especially when you get a seat on their awesome back patio. It’s a casual, laid-back place with good cocktails - some of which even come in larger-format “vases,” in case you find out you have a mutual interest in drinks made with mezcal and clarified watermelon juice. Plus, the short menu of Southern small plates won’t trap you into a long dinner if you discover that’s the only thing you have in common.
This West Town brewpub is in a remodeled old theater, which will give you something to talk about for at least three minutes before trailing off and staring at the beer menu in silence. It doesn’t have a very bar-y atmosphere - there are steampunk light fixtures, and hidden TVs that only come out when a Chicago sports team is in a playoff (so, not often). The food and beer are both solid (there are bar snacks like fried giardiniera and chili popcorn, and the burger is fantastic), and if you truly run out of things to say, you can always ask someone to give you a quick tour of the brewery in the back.
This Andersonville bar used to be very small, so if it was full when you arrived, there wasn’t anywhere to stand while you waited for a table. But they’ve expanded, and the space is much more comfortable now. There’s indie music playing at just the right volume, it’s busy but not unpleasantly so, and you can eat one of our favorite cheeseburgers in Chicago, along with other things like tacos and bao. On top of all that, it’s generally pretty dark inside, so if you haven’t updated your profile picture in a few years, you should be fine.
You agreed to meet after work in River North, but then realized that most of your options are either expensive steakhouses or loud bars full of people who recently auditioned for reality shows. Luckily there’s also Centennial, a low-key spot with a great craft beer selection and interesting bar food. Many of the dishes have an Indian twist, and the space - which looks like the hull of an old ship - is quiet enough that you can finally get to the bottom of all the plot holes in Titanic.
Cafe Marie-Jeanne is a casual place in Humboldt Park that serves rustic French food. The most important thing to know is that said food is really, really good - so if the date goes awry and ends early, just plan to circle the block for 20 minutes, then come back and finish eating by yourself.
OK, so you exaggerated your interest in fitness a little bit (you forgot to clarify that the 5k you mentioned was during cross country in high school). This can go unnoticed at Park And Field, which is designed to look like a turn-of-the-century gymnasium. In addition to having a “sporty” atmosphere without requiring any actual physical effort on your part, the space is just fun - there’s a giant patio with a retro camper that functions as a bar, some fire pits you can sit near well into the fall, and even a bocce court.
The West Loop is a busy neighborhood, and most bars there will have you yelling in each other’s faces to find out how long you’ve each lived in the city, and whether or not you’ve broken down and bought a car yet. The Press Room isn’t like this. It’s a wine bar in the basement of a building on a secluded side street, and it’s rarely crowded. They have a great selection of wines, really good cocktails, and a short small plates menu (with things like chicken liver mousse) that goes well with both. So it’s an easy place to hang all night.
Arbella is the cocktail bar right next to Tanta, and it’s owned by the same people. This place has a map-like drink menu that you can use to show each other the places you’ve gone backpacking and/or want to backpack in. All of the cocktails are inspired by various countries on the map, like the “PB&J” (peanut butter infused vodka and jelly ice) for the US, or a “snow cone” with sake, pisco, and Red Bull syrup for Antarctica (where you really shouldn’t go backpacking, unless you pack very carefully). After bonding over that, stay and share bar snacks like shawarma empanadas and small dishes like tacos, bao, and Korean fried chicken.
You haven’t officially met, but you’ve been texting each other, and you have a pretty good feeling about this person. Take them to Passerotto. Everything about this Korean restaurant in Andersonville is great, from the likeable small space to the friendly service and the excellent food. The menu is short, with some small plates, raw seafood, and a few noodle and rice dishes. If things go as well as you’re hoping, share something from the large-format section, too (like the kalbi).
Billy Sunday in Logan Square is designed for people who are serious about cocktails, and appreciate their usefulness in calming first-date nerves. This low-key spot looks like an old tavern, has a great menu of classic and creative drinks, and even does classes on the “history of spirits.” Which you can come back and take on your first anniversary, since clearly this date was a home run.
If you like the idea of hanging out in someone’s home, but not with a stranger (because that’s a bad idea), go to Scofflaw in Logan Square. This space feels like the drawing room of a Victorian house - it’s dimly lit and quiet, with old-timey chairs around a fireplace. The drink menu focuses on gin cocktails, and they also serve food, including fresh-baked cookies that only become available after midnight. Which makes this a good place to find out if your date might actually be a Gremlin.
Lone Wolf is in the West Loop, and it’s best known as the holding pen for people waiting for Au Cheval. But it happens to be a great place to hang out in its own right, with a large bar, plenty of comfortable booths, and tasty snacks. If you decide things are going really well, head next door and put your name in for a table. It might be ready by your second date.