CHIGuide
Where To Go For A Dinner You’re Dreading
When you have a dinner planned, and you really wish you didn’t, use this list.
Unless you’re in the habit of eating while watching the first two minutes of Up, you probably don’t have a lot of emotionally draining meals. But occasionally you just have to make plans with someone difficult, whose company depletes you like a video game power meter. When you’ve got an upcoming dinner that you’re dreading more than anticipating, use this guide to find a restaurant that balances out any unpleasantness, or at the very least will be a nice distraction until you can escape.
THE SPOTS
Perfect For: Your Visiting Almond Mom Who Wants To Meet Your Significant Other
Your mom—a Snackwell devotee in the ‘90s and a Goop subscriber now—is making her annual trip. Despite your best efforts, she wants to go to an actual restaurant where she can “get a little dressed up” and meet your significant other. Make reservations at Oakville in The West Loop. She can order the “nice green salad” (that’s literally what it’s called) and you can get whatever the hell you want from their all-over-the-place menu, whether it’s fried chicken, steak, or a pizza. She’ll still narrate what everyone is eating, but the sooner your partner learns to tune her out, the better.
Perfect For: Your Uncle Who Hates Chicago And Doesn’t Live Here
Your uncle, despite never living here, has a hatred of Chicago that makes you switch seats every Thanksgiving. Unfortunately his beloved team is playing the Cubs, and he decided to “deal with the traffic and whatnot” and force you into an obligatory dinner. You need someplace loud where you (and hopefully no one else) can hear what’s coming out of his mouth. So take that human megaphone to Joe’s Stone Crab in River North. You won’t be able to tell if he’s asking you to order another slice of key lime pie, or giving another anecdote about Chicago’s taxes. (Pretend it’s the pie.)
Sign up for our newsletter.
Be the first to get expert restaurant recommendations for every situation right in your inbox.
Perfect For: Your Visiting Parents Who Are Too Interested In Your Life
They love you very much, but dinner with your parents can be a battery of questions—how your dating life is going, the last time you got your teeth cleaned, and how exactly you manage to afford that fancy gym membership while paying off your student loans. Try taking them to Indienne, a nice River North Indian spot with delicious fusion dishes. It won’t stop the interrogation (nothing will), but you can answer personal questions in a restaurant that’s quiet enough that you won’t have to repeat yourself, but not so quiet that the tables on either side of you will be able to hear you admit that you haven’t been to the dentist in three years.
Perfect For: A Night Out With Your Friend Who’s Always Complaining
Too much time with a constant complainer will give you an exhausting emotional hangover the next day. Minimize the effects of all that negativity by suggesting dinner at Etta in Wicker Park. The space has two floors, two big, comfortable bars, and a rooftop patio to head off any gripes about having nowhere to sit, and the menu is wide-ranging enough that your friend should find something they like. Even if you spend the whole meal hearing about their sister’s overly expensive destination wedding, the food is excellent enough to buffer the experience.
Perfect For: The Friend Who Always Brings Their Kids
Children are a treasure, each one is a precious gift, and they’re usually nightmares to eat with. If your friend shuns iPads and insists on distracting Topher with wooden toys that all children hate, go to Coda Di Volpe, an Italian restaurant in Lakeview. It’s a child-friendly spot where Jesse can start screaming and no one (except you) will mind. The best things here are the Neapolitan pies that you cut at the table yourself, so just keep the scissors away from Abigail.
Perfect For: When The Sibling You Don’t Get Along With Is In Town
Just thinking about your high-strung sister stresses you out, let alone spending time with her one-on-one. But she’s here now, so take her (and all the family baggage) to Jeong in West Town. This Korean restaurant is decorated in neutral tones and has a soothing atmosphere that feels a little like the therapist’s office the two of you should probably be sitting in. They serve an eight-course tasting menu with an optional $67 wine pairing that's always a good idea. But be prepared for your sister to do the opposite of what you suggest, because that’s how she is.
Perfect For: A Double Date Where One Person Is Incredibly Boring
The law of averages says that on any given double date, one of the four people is likely to be a dud—and spending an evening listening to anecdotes about drywall installation is like breathing in carbon monoxide. The best move is to head somewhere fun and upbeat, where it’s not only acceptable, but encouraged, to get kind of drunk during dinner. Somewhere like Beatnik. It’s a small plates restaurant that looks like a Wes Anderson movie set, has a party atmosphere, and serves flavorful food (dishes like beef cheek arepas and sweetbread kebabs), all of which provides an antidote to being gradually poisoned by the slow drone of the voice across the table.
Aba
POWERED BY
Perfect For: Dinner With Your Friend Who Belongs On The Real Housewives Of The Southport Corridor
Your most dramatic friend can be entertaining, even if after 10 minutes you wish you could mute them. But they are who they are, and they’re not going to change, so it’s a good opportunity for a trip to Aba. It’s a sceney, crowded restaurant in the West Loop serving very good Mediterranean food. It has everything your friend might need for their own drama to blend in: a bouncer with an earpiece, two crowded bars, and plenty of attractive people crying in the bathroom. This is a spot where theatrics can be safely released like an electrical pulse so you can focus on what’s important—the hummus.
Perfect For: Your Colleague Who Was Recently Passed Over For The Promotion You Got And Has Suspiciously Invited You To Dinner On A Random Thursday
An evening with an agenda-driven person is like a scrolling level in Super Mario Bros. where you’re continuously leaping from platform to platform: it’s precarious and requires a lot of concentration. It’s not the time for a restaurant that calls for sharing and/or small-plates negotiations—you need an uncomplicated classic like Gibsons. Everyone can order their own thing, and there are plenty of round tables so there won’t be any seating hierarchy. This leaves your mind free to craft the perfect response to their out-of-the-blue question about your Myers-Briggs results.
Perfect For: That Person You Can’t Put Off Getting Together With Anymore
Eventually, you run out of excuses and have to schedule a meal with someone who needs to “pick your brain” or an old roommate who wants to rope you into their designer protein powder pyramid scheme. You want someplace relatively fast (but not insultingly so) that has good food and an enjoyable atmosphere. Enter Middle Brow Bungalow, a cute brewpub in Logan Square with a short menu of pizza and toasts. You won’t need much time deciding what to order (pizza...or toast) and it’s open during the day, so you don’t have to give up one of your precious free evenings being polite.
Perfect For: Catching Up With Your Friend Who Always Uses Your Shoulder To Cry On
It’s important to show up for friends going through a rough time, even the friend who is going through a “rough time” 100% of the time. Take them for a pick-me-up at Boonies. This Filipino restaurant has an excellent menu (make sure to get the sisig), along with the Feel Good Factor™, meaning it will help put your friend in a better mood even if they just found out their ex is taking sole custody of Mr. Buttons.
Perfect For: The Person Who Makes It Obvious That They’re Just Waiting For Their Turn To Talk The Entire Time
Whether it’s a coworker or a particularly self-involved friend, some people will just talk at you the whole time you’re together. It’s kind of like being with a TV, so you might as well go somewhere with actual TVs to entertain you while your dinner companion goes on about their last performance review or new workout routine and never asks about yours. Daisy's has excellent po' boys and hurricanes, and a large bar area with strategically placed screens for your eyes to wander to.
Perfect For: Dinner With A Constantly Bickering Couple
Maybe it’s a part of their courtship, or maybe they’ve had too much exposure to reruns of Everybody Loves Raymond, but these two are constantly snipping at each other, and you can’t avoid them forever—so book a small group dinner at MingHin in Chinatown. The casual atmosphere at this fantastic dim sum restaurant is relaxed and fun, and the staff is laid back and friendly. Plus, the endless arguments will be interrupted every time an order of pork buns or soup dumplings is dropped off at the table. Drag this peaceful moment out as long as possible.
Perfect For: A Friend Date With Someone Who’s Aggressively Cheerful
Someone who pathologically points out silver linings in everything can be just as annoying as a constant complainer. You’ll never get them to acknowledge that some people need to stay off social media, and they even have some spiel about how, actually, mosquitoes are good for the ecosystem. Have a little fun with it—choose a place that challenges their ability to put a positive spin on every little thing. Take them to Le Select and watch as they struggle to see the bright side of the loud, expensive, confusing dining experience they’re having. Yeah, you’re stuck eating that meal too, but it’s worth it if they’re suffering with you.
