Maybe you enjoy double dates. Maybe you hate them. Either way, you’ll probably find yourself on one at some point. If you’re lucky, you’ll like both halves of the other couple. But the truth is, there’s a good chance one of them is the type of person who complains like it’s an Olympic sport - and eats all the bread.
No matter the circumstances, you need a certain kind of restaurant. Someplace where you won’t have to awkwardly stand around waiting for a table, or split a two-bite small plate between four people. Someplace where the food is good enough to make up for potentially boring conversation. Who knows? Maybe you’ll end up having a really good time.
If you’re looking for a leisurely spot where you can discuss important topics like whether Nagy should have started Justin Fields, book a table at Dear Margaret in Lincoln Park. This charming BYOB French-Canadian restaurant has tasty dishes like foie gras terrine with fluffy milk bread, duck breast with lentils, and a friendly team who will leave you alone while the four of you get to the bottom of why the O line is so terrible. In other words, it’s exactly the kind of place where you will want to take extra time to finish off that wine you brought.
It would be easy to drive right by Osito’s Tap - this small bar is hidden on a side street along the busiest stretch of Little Village. But that also means this quiet little bar never gets too busy. It has shareable bar bites like tlayudas or wings tossed in a tasty mole, a great side patio, and is a perfect spot for drinking and laughing with the only other couple you’d consider going on vacation with.
For someplace that’s popular and busy but not full of chaotic energy, check out Andros Taverna. This Greek restaurant in Logan Square is spacious, has good food, and you can usually get same-week reservations. Plus, that busy-ness means that the entire restaurant won’t hear the other couple when they start to argue about their dog. In terms of food, you’ll find appetizers like the must-order kataifi cheese pie (shredded filo layered with cheese, baked, then topped with honey and pistachios), mezze spreads, entrees like prawn saganaki in a rich tomato sauce, and the best spanakopita we’ve ever had.
En Passant is a cute, casual restaurant in Logan Square that’s full of delicious things. The escolar topped with black garlic honey made us realize how much we love black garlic honey, the chicken liver mousse is delightfully airy, and there’s an incredible smash burger topped with marie rose sauce and balsamic onions. The restaurant itself is small and dimly lit, with vintage touches (like chandeliers and candles) decorating the space. Just don’t get carried away by the charm and accidentally agree to go antiquing with them next weekend.
You’re out of excuses and backed into a corner - you’re finally going on a double date with that couple from the dog park. And you’ve just realized you don’t know anything about these people except that they have a Labradoodle. Go to La Storia, a Gold Coast spot with reliably good Italian food. While most places in the neighborhood are either high-end or ultra-casual, this place is nice but still relaxed, and best of all, you won’t be forced to share a bunch of small plates. (Still, get a pasta or two for the table.) If it turns out these people aren’t much fun, leave early and say you need to take the dog out. They’ll understand.
El Che Steakhouse & Bar
This Argentinian spot is a good place go with your friends who like to host parties, and always get too drunk before the guests arrive. It’s fun and a little loud, with an open kitchen and a live fire grill. Everything that grill touches is worth ordering - the steak is good, and you shouldn’t overlook the grilled oysters or the vegetables, either. Plus, you won’t have to rely on any wasted friends to be in charge of your food.
Mi Tocaya is the definition of a feel-good neighborhood spot, and it’s a good option if one half of the couple you’ve made plans with is a downer. The friendly service, lively environment, and great Mexican food make it pretty hard to be negative while you’re here. Try to come during the summer when the patio is open - even if it doesn’t turn this person’s mood around, it will probably make it more bearable for you to listen to the details of their three-hour phone call with Comcast.
Recess in the West Loop is a theme bar, and the theme is basically “City Hall,” which means menus are made to look like municipal forms and cocktails have names like the “Alderman’s Choice.” And while government buildings and red tape aren’t what we’d normally consider a good time, we promise this place is fun. The outdoor space is huge (14,500 square feet), and includes tables situated inside repurposed shipping containers, giant games of things like Connect Four, and it even has an outpost of Bob’s Pizza. In conclusion, come here, play games, get drinks, order pizza, and be glad you decided not to cancel.
S.K.Y. in Pilsen is a good place to go when you like both of the people you’re on a double date with, because it’s the kind of place you’ll want to keep hanging out in after you’re done eating. The ambience feels a bit like a low-key house party in someone’s cool basement. And while it’s hard to definitively classify the food here - it’s inspired by a lot of different traditions, from Korean to French - everything is really good. You can expect things like cornbread madeleines, lobster dumplings in a buttery lemongrass broth, and fried chicken with a fermented hot sauce. If you do feel like a change of scenery after the plates have cleared, head across the street to Dusek’s for drinks at the Punch House.
Sushi-san in River North has wooden tables, loud rap music, and a mix of traditional and contemporary Japanese dishes. The upbeat atmosphere and reasonable prices go a long way toward making sure everyone will have a good time, even if all four of you would rather be at home watching that new documentary about medieval siege engines. We recommend focusing on the nigiri and sashimi (their “San-sets” come with an assortment of pieces meant for sharing). And make sure you get the Japanese pancakes for dessert - you’ll be glad you left the house for those alone.
This small cocktail bar in Albany Park has a lot going on There’s a long drink menu of classic cocktails, fancy bar snacks like chicken liver pate, and live DJs on the weekend. But, it all works well together, and makes for a great double date spot, especially because you can all either stay for drinks, or stick around for food if you’re actually having fun.
Sharing-focused restaurants can be tricky when you’re on a double date - splitting three oysters between four people gets awkward fast. But the large portions at the Publican make this a non-issue. Plus, the well-rounded American menu will have something for everyone, and the food is consistently good. If sharing food is already a lot for you, know that you don’t also need to sit at the giant, U-shaped communal table while you do it - opt to sit at one of their closed-in booths instead.
Your roommate’s long-distance boyfriend is visiting from the West Coast, and you want to go someplace that will help encourage him to move here. After all, your friend’s constant third wheeling is getting old. Go to Giant in Logan Square, where they make a Midwestern dish like broccoli and cheese a must-order, and their pastas, like the tagliatelle with crab and uni butter, are fantastic. In other words, we’ve yet to eat something here we didn’t like. Plus, the casual space has lots of upbeat energy. Make sure the West Coaster visits during the summer, not when it’s 5 degrees outside, and it should all work out.