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.
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.
On double dates, you typically don’t want to go anywhere that seems too romantic, and Maude’s Liquor Bar fits that bill, if you sit downstairs. Unlike the upstairs area, which is dark and quiet, the ground floor has a casual French bistro environment that’s perfect for a small group. A lot of the dishes here (like the moules frites) are good for sharing, but there are plenty of options you won’t have to share, too - so you can still have a cheeseburger all to yourself.
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.
Don’t attempt to eat here if you’re making plans with people who always cancel at the last minute. You need to buy tickets ahead of time (the cost is applied to your dinner), and this doesn’t work with flakey couples. Do reward your considerate friends with dinner here. Roister is from the people behind Alinea, but far more casual (keep in mind that “casual” in relation to Alinea is not casual in the grand scheme of things), and the food is fantastic. Make sure to order the fried chicken platter (which is large enough for four to share) and at least four foie gras candy bars, since each person will probably want their own.
Arranging to go to Girl & The Goat for a double date is a bad idea. It books far out, so you run the risk of at least one person not being in the picture anymore by the time the date arrives. Duck Duck Goat is Girl & The Goat’s sister restaurant, and it’s much easier to get into. The food is Chinese with some interesting twists - for example, wonton soup with a blueberry base. You can usually get same-week reservations, so you won’t have to worry about explaining Sammy’s ex’s whereabouts to your host.
This place doesn’t take reservations, but we’re putting it on here anyway. Not only because it has very good pizza, but also because it’s close to Second City - a popular double date destination for people trying to use the theater tickets their companies might have given them over the holidays. There’s a mixture of creative pies (the littleneck clam is a standout) and classics, like a soppressata pizza made more interesting by the addition of Calabrian chili honey. There are quality salads, too - like one with roasted beet and tahini - and you can get your pizzas half and half, so there’s no need for an argument over what to order. Unless you’re with Janice and Dave, who argue about everything.
Go to Bar Biscay with that couple you actually like enough to travel with, since this West Town brasserie will make you feel like you’re eating on the coast of Spain. There are good seafood options, like whole prawns, plenty of things with anchovies, and pintxos of brandade on toast. The space is casual, with neon lights that somehow don’t come off as corny, and there’s a busy, crowded atmosphere. It’s the perfect spot for the four of you to plot your next trip.
Most of the Italian restaurants on Taylor Street are fine, but for a double date, our pick is Davanti Enoteca. It’s a kind of small, always crowded place. There are some dishes that work well as share plates (like the polenta with the ragu of the day), plus great pasta you won’t want to share with anyone (the cacio e pepe, for example). You could easily eat here without realizing that it’s technically part of a small chain (the other locations are in San Diego). Then again, if your friend’s new boyfriend originally suggested The Cheesecake Factory, maybe you should let him know.
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.
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.
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.
Chicago has a lot of creative burger places, and many of them are really good. But Bad Apple is our go-to for a double date. It has interesting burgers (among them one with peanut butter and bacon), plus a chill neighborhood atmosphere. It’s busy without feeling slammed, so it’s perfect if you want to be able to have an actual conversation.
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.