CHIGuide
Where To Go On A Low-Stakes Date
photo credit: Kim Kovacik
Going on a date with someone you barely know is like playing poker. You don’t want to go all in at an intimate restaurant full of couples staring into each other’s eyes, or spend money at a hotspot that’s so crowded you’ll wait an hour for your food and have to yell “so what kind of movies do you like?” at someone you might never see again. You need a place where you can get to know each other, without looking like you’re trying too hard. Somewhere with good food, that’s easy-ish to get into, and not too expensive. You need one of the places on this list.
THE SPOTS
A study from GrubHub and Match found that sushi on a first date increases the odds of having a second date by 170 percent. Assuming that’s your goal, Sushi-san in River North is a great option. This laid-back spot has wooden tables, loud rap music, and a mix of Japanese dishes. Share one of their San-sets (an assortment of sushi) for $100 or less, get the Japanese pancakes for dessert, and laugh over their use of the poop emoji as a bathroom sign. And if your date doesn’t think that’s kind of funny, maybe reconsider the second dinner.
photo credit: Kim Kovacik
Not only does this New Orleans-inspired Hyde Park spot have the best po’boys we’ve encountered in Chicago, but Daisy's isn't too expensive and is also a blast. The spacious counter-service restaurant has a full bar, occasionally has live music, and makes boozy hurricanes that aren’t overly sweet. And if your date turns out to be the kind of person who just kinda talks at you the whole time you’re together, the large dining room has strategically placed screens for your eyes to wander to. It’s kind of like being with a TV, so you might as well go somewhere casual with actual TVs to entertain you.
photo credit: Daniel Kelleghan
Esmé in Lincoln Park is fantastic, but a $235, 15-course dinner might make them think that there’s a ring hidden in the dessert. Plus, you don’t want to commit to three hours of being together. For a more casual experience, check out Bar Esmé, their a la carte restaurant next door. The menu is full of delicious dishes like a playful bouquet of giant Flamin’ Hot Cheetos or pork loin with spaetzle and a fragrant burnt onion jus. They also have a great wine and spirits list, and though there isn’t a cocktail menu, the bartenders make fantastic off-the-cuff drinks. The bright space has a handful of tables for two and some bar seats, so it’s nice and cozy, but not so cozy that you feel obligated to start brainstorming couple names.
photo credit: Sandy Noto
This Logan Square restaurant’s colorful space is always fun, buzzing with chatter and playing music that's loud enough to fill awkward silences. And if your date ends up having the conversational skills of a Madame Tussaud’s wax figure, at least Mi Tocaya Antojeria’s fantastic Mexican food can entertain you. Though the menu rotates, you can expect great dishes like tender lengua with a spicy peanut butter sauce, and order anything with their soft corn or flour handmade tortillas—like a bubbling bowl of birria or a crispy chorizo taco.
photo credit: Reilly Drew
Pompette is an all-day wine bar in Bucktown, and it’s one of those cute little restaurants that’ll make you say “what a cute little restaurant” when you sit down. The narrow space is sparsely decorated with a couple of plants and hanging globe lights, and just bright enough that you won’t want to linger. The menu is mainly small plates from a team of chefs who worked at tasting menu spots like Alinea, Elske, and Moody Tongue. They have tasty things like crab croquettes sitting on saffron aioli, grilled shrimp with butternut squash, and spaghetti in a mushroom cream sauce. It’s the kind of useful place you go to on a low-stakes date, where you can convincingly lie to each other afterward and say “let's do this again.”
Sochi’s bustling, bright dining room and close tables will discourage oversharing. And while this Lakeview Vietnamese spot is casual, it’s still sleek enough to feel like you made some effort. As you get to know each other (hopefully without having to hear the reason they're banned from Jewel) you can snack on crispy egg rolls and split a refreshing seared duck salad. For larger plates, you can’t go wrong with any of their fried rice options, like garlicky slap mama fried rice. If you make it to dessert without wanting to bail, definitely split the light and fluffy cheesecake topped with housemade jam.
Unless you've been doing some social media stalking (or actually thought to ask) you might not know what your date likes to eat. That’s where Lula Cafe comes in: This casual restaurant in Logan Square has plenty of options. The farm-to-table menu has a variety of pasta, meat, and seafood to choose from, plus a strong selection of vegetable-based dishes. Service here is friendly, but not intrusive—so you won't have to dodge questions like “so, when are you two getting married?” The cozy dining room manages to fit a lot of tables (each with its own little candle) in a small, semi-dark space. But you’ll also have families and kids around to act as a buffer in case your date turns out to be a self-employed venture capitalist.
photo credit: Kim Kovacik
Little Victories is the kind of casual place where you can drop by to meet someone that you’ve only spoken to over DM. It’s a great bar for an early-in-the-game date because it’s got the necessities (dart boards, pool table, jukebox) but is nicer than the dive bar you were considering. It feels a bit like a 70s rec room, with wood paneling and lots of plants. Plus, it has great bar food like burgers and spinach dip, and plenty of outdoor and indoor seating.
