At some point, one person in your life will need to meet another person in your life. Maybe you’re introducing your significant other to your friends, your friends to your co-workers, or your accountant to your parole officer. Or maybe you’re the person being introduced to someone for the first time, and you want to minimize the awkwardness as much as possible. Whatever the situation, you need someplace with great food and drinks, and an environment where everyone feels comfortable. Here are 13 great options when you need to arrange a playdate for adults.
It’s time to introduce your new girlfriend to your (very) judgmental sister. Go to Giant in Logan Square. The new American food here is always creative and well-prepared, and even the most critical person is bound to enjoy their meal. Start out with fried uni shooters, and make sure one of the pastas (like the crab tagliatelle) is on the table. We can’t guarantee your younger sibling won’t find something wrong with your girlfriend, but at least she won’t be able to complain about the food.
Yes, you’re an adult and extremely mature. But that doesn’t mean it’s not awkward that your mom is remarrying, and you’re suddenly going to have 28-year-old step-sibling. Meet this person you’ll (hopefully) never have to share a bunk bed with at Soule in West Town. The soul food is excellent, and the friendly atmosphere will ease any potential tension. Make sure to pick up some beer or wine beforehand (it’s BYOB), and if you two get along and/or there’s a wait for a table, bond over complaining about your parents over drinks at Cleo’s next door.
You have everything planned for your buddy’s bachelor party this weekend, but some guys decided to fly in a day early. Take these people who don’t know each other to Funkenhausen. It’s a German-inspired restaurant that’s fun without being obnoxious, so everyone can have a good time without getting too exhausted before the weekend really starts. The menu is pork-heavy, and changes often - but you’ll typically find delicious things like housemade weisswurst, a twist on spaetzle, and (if you’re lucky) schnitzel.
The exchange student who stayed with you during your regrettable high school goth phase is in Chicago for the weekend. She’s probably changed as much as you have, so you want her to meet your friends someplace that will work whether she’s still fire dancing in Berlin or she’s taken up beekeeping (or possibly both). Summer House Santa Monica has a well-rounded new American menu with a lot of options - including plenty that are kind-of-healthy - and the bright, summery space is nice to spend time in, even during the winter when it’s dark out. Like your tortured 11th grade soul.
Double dates can be tricky if two of the significant others involved haven’t met yet. But Middle Brown in Logan Square can help. It’s a cute brewpub that’s decorated like a DIY wedding (with tea lights, reclaimed wooden picnic tables, and decorative plants in birdcages), and perfect for small groups. Get anything that involves the housemade bread (like the toasts and spreads), plus the pepperoni pizza, and order plenty of their light and hoppy beers. If everyone gets along, consider solving mysteries together, or starting a band.
Your parents and your fiancé’s parents are meeting for the first time. You need someplace that’s nice but not too expensive, and quiet enough to navigate delicate topics like money, politics, and whether you’re planning to raise your children “Lou Malnati’s” or “Pequod’s.” La Storia in the Gold Coast meets all the above requirements, and also has great Italian food - in particular the housemade pastas, and entrees like chicken Milanese. But no matter how well things seem to be going, don’t bring up the fact you’ve been researching Pizzeria Bebu-style parenting on the side.
You keep hearing about how nice your roommate’s best friend from high school is, and she’s going to be staying with you guys for a few days. You want to make a good impression. Head to Passerotto in Andersonville. It’s a charming restaurant (for example, it has cute drawings of French bulldogs on the wall), and it has fantastic Korean food, along with an extensive wine list and extremely nice servers and bartenders. In other words, hopefully this spot will make up for the fact that you swore at three other drivers on the way to the restaurant.
When you need a casual place to introduce two people (like a subletter to your roommate who just found out you’re spending six months in Costa Rica), this all-day market and cafe in West Town is ideal. It’s a great spot to have breakfast or lunch (they have things like pastries, toasts, and sandwiches), or to have roast chicken for dinner while you discuss the fact that someone will have to take care of your cat.
If this is the type of situation where a larger, disparate group of people need to come together for the first time (i.e. a wedding weekend), go to Ema. It’s a very good Mediterranean restaurant in River North, with dishes that are meant to be shared (like baked halloumi, hummus, and spreads). As a bonus, there are plenty of round tables that make it easy for people to talk and get to know each other. A good topic of conversation: reasons everyone thinks the marriage is doomed.
If you grew up outside of the city, at some point your suburban friends will have to meet your city friends. Two worlds are colliding, and you need a place that works for both of them. Siena Tavern is good for this. It’s a big, sceney River North restaurant that will give your non-city friends the fun downtown Chicago atmosphere they want - and the Italian food (like fantastic pastas and pizzas) is also delicious enough to keep your jaded fellow Chicagoans happy.
Congratulations, the person you’ve been dating has finally leveled to the stage of meeting your friends. Get everyone together at The Delta in Wicker Park. It’s a small bar and Southern restaurant, and it has a casual atmosphere and laid-back service. It’s a great spot to talk, drink cocktails, and eat food like tamales, very spicy fried chicken, or an excellent burger.
You’ve been talking to your friends nonstop about the guy you fell in love with when you were in Prague, and he’s finally visiting. But this is Chicago and it’s O’Hare, and his delayed flight is ruining all your well-organized plans. Luckily, Owen and Engine is open until 12am, and the English pub-style atmosphere is relaxed, with comfy leather chairs upstairs that will feel nice after 10 hours of being crammed on a plane. The fish and chips or burger will also appeal to anyone who’s starving after spending an hour on the tarmac.
After you drop your luggage off at The Real World house, you and the six other strangers in the cast should grab dinner before the camera crew shows up. Head to Qing Xiang in Chinatown, which is perfect for a group dinner. Their broth-filled dumplings are all available steamed, boiled, and fried, and you can choose fillings like pork and pickled cabbage, shrimp and leek, or egg and pepper. Then decide this season you’re going to be the “shy housemate who avoids conflict.”