Where To Introduce People When You Want Them To Get Along

15 places with great food and minimal awkwardness.

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 15 great options when you need to arrange a playdate for adults.


photo credit: Kim Kovacik



$$$$Perfect For:Casual Weeknight DinnerDate NightLunch

This Vietnamese restaurant is perfect for minimizing any chance of conflict. Sochi has garage-style windows that brighten up the large dining room, and the space is nice—but won’t make anyone feel underdressed. Plus, the busy dining room and close tables will encourage polite conversations you’re willing to have a stranger overhear. As you all get to know each other (hopefully without having to use the word “homewrecker”), you can eat crispy egg rolls and dishes like the slap mama fried rice. If you make it to dessert without someone storming out of the restaurant in tears, order the fluffy cheesecake topped with housemade jam.

Obelix will distract everyone with impressive food versus giving them time to prod your friend about why you were detained in Switzerland. On the surface, This River North spot looks like a typical, white-tablecloth French restaurant. It’s not. Obelix expertly walks the tightrope of feeling formal without being stuffy. And that same balance is present in its menu, which is filled with a mixture of classic dishes like escargot and playful, fusion-y ones like the foie gras-filled taco.

Congratulations, the person you’ve been dating has finally leveled to the stage of meeting your friends. So get everyone together at Daisy’s in Hyde Park. This large Southern restaurant has a casual atmosphere, and laid-back service. It’s a great spot to talk, drink cocktails, and eat po’boys and fried chicken while listening to jazz or New Orleans bounce.

Yes, you’re an extremely mature adult. But that doesn’t mean it’s not awkward that you’re suddenly going to have a 28-year-old step-sibling. Meet this person you’ll (hopefully) never have to share a bunk bed with at Gretel in Logan Square. The bar food is excellent (especially the burger) and the friendly atmosphere will ease any potential tension. They don’t take reservations, but if there’s a wait for a table, you can bond while complaining about your parents over drinks atthe speakeasy in the basement.

photo credit: Kim Kovacik

There are a lot of just-fine Italian restaurants in Chicago that are inoffensive enough to be on this guide. But if you want to inject a teensy bit of fun into the long-awaited meeting of your undergrad roommate and your postgrad roommate, go to Segnatore in Humboldt Park. The food at this relaxed spot stands out because every dish has some kind of unexpected twist. The meatballs are filled with melted scamorza, offering the benefits of a Juicy Lucy without the risk of third-degree burns. The deconstructed lasagna is a pile of garlic mafaldine, whipped ricotta, and a mushroom bolognese that would win in a steel cage match against any meat version. And Segnatore has the kind of a relaxed vibe of a European cafe we want to sit in all day.

photo credit: Kim Kovacik



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If you’re looking for a leisurely spot where your future in-laws and parents can commiserate about your wedding photographer and flower costs, book a table at Dear Margaret in Lincoln Park. This charming French-Canadian restaurant has tasty dishes like foie gras terrine with fluffy milk bread, duck breast with lentils, and a friendly staff who will leave you alone while the parents get to the bottom of “why everything is so dang expensive.” It’s exactly the kind of place where you’ll endure another 20 minutes of parent-talk to order some dessert.

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. Alla Vita is good for this. It’s a big, sceney West Loop restaurant that will give your non-city friends the fun Chicago atmosphere they want—and the Italian food (like the ricotta dumplings and pizzas) is also delicious enough to keep your jaded fellow Chicagoans happy.

Apolonia, a mostly Mediterranean restaurant in the South Loop, is from the same team as S.K.Y. in Pilsen. But while its sister restaurant feels like a sexy basement, Apolonia is bright and airy, with tall windows and high ceilings. There are dishes like mussels on toast, a buttery truffle puff bread, and fiorentini topped with a rich pork sugo. There aren’t a lot of upscale restaurants near the McCormick center, but this understated spot is nice enough that your Chicago team can meet up with visiting colleagues who are at the Morningstar Investment Conference.

It’s time to introduce your new girlfriend to your (very) judgmental sibling. 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 crab salad, and make sure one of the pastas (like the tagliatelle) is on the table. We can’t guarantee your sibling won’t find something wrong with your girlfriend, but at least they won’t be able to complain about the food.

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.

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.

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