Whether you’re hanging out one-on-one with a friend you usually only see in group settings or an ex who recently liked six of your pictures on Instagram, you’re not completely certain whether this get-together is a date. But before you’re able to figure that out for sure, you’ll need to choose a place to meet.
You don’t want a wine bar full of couples looking longingly into each other’s eyes, and you also don’t want a bright, quiet cafe that feels like your college library. It shouldn’t be expensive or very crowded, but you still want it to feel impressive, and you should be able to either leave after half a beer or order some food and hang out for a while.
Whether or not you want this to be a date, two things are for sure: first, you hope this person feels the same way you do. And second, you should go to one of the 13 spots on this guide.
It’s hard to tell what this person thinks of you - it takes them a day and a half to respond to your texts, but when they do it’s with a blushing emoji and extra vowels. Go to Saint Lou’s, a restaurant in the West Loop that serves things like patty melts and mac and cheese. It’s not romantic at all, but the dimly-lit attached bar, Moneygun, is. So if it turns out their phone just has terrible service (to go along with their terrible taste in emojis), follow up with some cocktails next door.
A former coworker who always complimented your taste in music wants help picking out some vinyl for their new record player. Since the internet exists (and you haven’t talked to them in three months), this seems like a flimsy excuse to see you. Take them to Dorian’s in Wicker Park, a speakeasy bar with a small record shop in front. After choosing the perfect Otis Redding album, see if they want to stay for drinks. If not, tell them about Reckless Records around the corner, then grab a seat at the bar by yourself.
After you made dinner plans they said “it’s a date,” but you can’t tell if they meant it, or were casually saying it like “it’s a plan." Spacca Napoli is good for this situation - it’s a cute spot in Ravenswood with a nice streetside patio and excellent Neapolitan pizza. There will definitely be groups of friends and a couple of families with kids glued to their iPads here, so you’ll have plausible deniability in case it’s not actually a date. Just make sure to tell the violinist to wait for your signal.
You’ve already been on a few maybe-dates with this person, and still can’t tell if it’s going anywhere. If things ever get real between you two, you might go on an actual date at Mott Street - one with reservations and servers. But until then, head to its counter-service spin-off Mini Mott in Logan Square. It’s a great burger place that also has things like chicken katsu sandos and sambal wings. Afterward, you can platonically enjoy soft-serve taiyaki cones together.
Your parents set you up with a family friend who “loves TV, just like you." You only agreed to go to be polite, and assume they did too. Plan on grabbing a quick bite at Kimski, a casual spot in Bridgeport with great Korean-Polish food and a nice patio. Then if it turns out you have other things in common besides just enjoying television, you can keep the night going at the attached bar, Maria’s.
If your ex reaches out to see if you’d be open to drinks, head to Best Intentions in Logan Square. It’s a little divey, but since it’s nicer than the actual dives you used to take them to, you can show that you’ve grown up since then. The cocktails are excellent and their burger is great - it’s a little messy to eat, but they’ve seen you in much worse shape. Like the week you went without showering because you lost a bet.
Your college crush just moved to the city and asked if you want to grab dinner and catch up. Tell them to meet you at Superkhana, a fun Indian restaurant in Logan Square. With dishes like a “psychedelic” grilled cheese and bathrooms that play TLC’s Waterfalls on repeat, this place doesn’t take itself too seriously. And neither should you when it turns out dinner is just a “thank you” for introducing them to their husband.
After running into someone from high school at Mariano’s, you’re meeting up for drinks. For the first time, you almost regret deleting your Facebook because now you have no idea if they’re in a relationship. Go to Sleeping Village, a bar and music venue in Avondale that has plenty of big booths that are great for catching up. After they mention that it’s exactly the type of place their boyfriend’s band should play at, you can just smile and be glad you didn’t reactivate your Facebook account after all.
If you’ve resorted to using a Magic 8-Ball to help you decide between a sit-down restaurant or a bar, go to Pub Royale in Wicker Park. It’s a bar serving great Indian food that’s way better than the defrosted buffalo wings you’ll find at some of the other spots in the neighborhood. This way you’ll only need help deciding whether to leave after a few drinks or stay and split an order of lamb vindaloo.
After three months of messaging @craftcutie73 on beer forums, the two of you finally decide to meet up in real life. You should do this at Beermiscuous, a bar in Lakeview with hard-to-find beers. The space feels like a cafe - you’ll probably see some people working on laptops - but there are also comfortable chairs and a cozy fireplace. Even if there’s no wedding in the future for @craftcutie73 and @mikelikespilsners, at least you’ll both enjoy yourselves here.
You’re both adults, and you need to go someplace where you can be clear about what you want - even if what you want is to bake cookies and find someone to split a gym membership with. Head to Eleven Eleven, a quiet wine bar in the West Loop, and be direct about how you feel. That way you’ll know for sure whether it’s a date, and you can throw away the “do you like me: check yes/no” note you wrote.
Cafe Marie-Jeanne is a casual all-day French spot in Humboldt Park, and coming here doesn’t scream “I’m trying to date you” like an 8pm dinner reservation at Maude’s would. Servers wear t-shirts and jeans, and there'll probably be somebody at the bar getting work done over a glass of wine and some fries. But the food is excellent, so even if this person doesn’t immediately fall in love with you, at least they’ll appreciate your taste in restaurants.
Since you’re not exactly sure what situation you're walking into, you need to stay flexible, and Marz makes that easy. It’s a brewpub in Bridgeport with all types of beer and non-alcoholic drinks, has food like cheese boards and Chicago-style fried bologna sandwiches, and feels like a mix between an art gallery (classy) and a warehouse (less classy). It even has its own little arcade that you can hang out in after dinner if it turns out they wanted to meet up for more than just real estate advice.