The Awkward Dinner Guide

Where to go to make awkward dinners a little less awkward.

Hopefully, most dinners in your life are about enjoyment. But some dinners are just an hour of your life you have to get through. Some dinners are awkward.

Whether you're entertaining distant relatives, or you're out with your boss hoping they don't fire you, or you're eating with people you haven't seen from high school, awkward dinners don't have to be terrible. Here's where to go in several different awkward situations and still get out alive.

The Spots

Roberta’s review image


Pizza in Brooklyn


Get Directions  |   718-417-1118  |  Website

Hours: THURSDAY11:00AM to 12:00AM
    Perfect for
  • Birthdays
  • Brunch
  • Day Drinking
  • Kids
  • Lunch
  • Outdoor/Patio Situation
  • Walk-Ins

Suitable For: Dinner With Hip Distant Relatives From Overseas Who Are Coming To NYC For The First Time And Messaged You On Facebook

Someone you're related to in ways you don't totally understand (something about a grandmother's cousin) is here from Oslo or Sao Paulo, and because you're a good person, you're going to show them the city for a night. These people are probably staying at an AirBnB in Bushwick already, but even if they're not, give them the Brooklyn they've heard so much about and take them to Roberta's.

Tsushima review image


Japanese in Midtown

    Perfect for
  • Casual Weeknight Dinner

Suitable For: Lunch With A Boss You Have An Awkward Relationship With

You've done everything you can to try and forge a relationship with this person - asked about their kids, tried watching the same TV shows they do, even maybe learned to play golf or feigned interest in a high intensity fitness class just to get in some quality time. But no matter how hard you try, this relationship remains awkward. When your boss mysteriously mentions that you should put a lunch for the two of you on the calendar for next week, don't panic - no one gets fired over lunch. Go for sushi and keep it straightforward at Tsushima - this isn't the time to get a meal at Yasuda. Tsushima is good quality, but not fussy or expensive. That's why we listed it in on our Midtown Sushi Guide as the place you go for a simple meal out with your boss.

Aria Wine Bar review image

Aria Wine Bar

Wine Bar in West Village


Get Directions  |   212-242-4233  |  Website

Hours: THURSDAY11:00AM to 10:00PM
    Perfect for
  • Drinking Good Wine
  • Drinks & A Light Bite
  • First/Early in the Game Dates
  • Private Dining
  • Small Plates

Suitable For: Confronting A Cheating Partner

Sure, you could do this like a mature adult on the couch in your apartment, or on a park bench or something. But how are you going to get this a**hole to a park bench? Right. So you're going to need a restaurant with a few elements to do this correctly. First, it should be dark and loud, so staring from others will be minimal. Aria in the West Village is both of those things, plus the waiters are very nice, and if you end up at the bar alone here, it won't be so bad. That said, you also want a place where you won't really be that upset if you can never come back here again, and Aria can also fit that bill.

Jack's Wife Freda review image

Jack's Wife Freda

Diner in SoHo


Get Directions  |   212-510-8550  |  Website

Hours: THURSDAY8:30AM to 12:00AM
    Perfect for
  • Brunch
  • Casual Weeknight Dinner
  • Coffee & A Light Bite
  • Lunch
  • Vegetarians

Suitable For: A Meeting With Your Friend's Sister Who Wants "Career Advice"

Your friend's 23-year-old sister Jessica graduated from Emory last year, and is already looking to change careers. Consulting just isn't that fulfilling, you know? As resident person-with-a-job-that-sounds-interesting, you've been called upon to offer up some direction. You feel a little flattered that people look up to you, but you also don't want to make this last too long. You want to keep this meal short and sweet and fairly affordable, and you can do that at Jack's Wife Freda. Plus, Jessica's probably been really wanting to come here anyway.

The Marshal review image

The Marshal

American in Hell's Kitchen


Get Directions  |   212-582-6300  |  Website

Hours: THURSDAY4:00PM to 12:30AM
    Perfect for
  • Breakfast
  • Date Night
  • Dinner with the Parents
  • Lunch
  • Pre-Theater Eats

Suitable For: Dinner With Someone Who Won't Stop Talking About How They Hate New York

This person is most likely staying in Midtown - remember, they're here because they have to be, not because they want to be. As much as you may be tempted to show this person the West Village or Chinatown and let them see the city isn't all people in Times Square trying to give you tickets to a free comedy show, save yourself the work and just ease their misery slightly by taking them to somewhere easygoing nearby. Everyone at The Marshal in Hell's Kitchen is super friendly, and the food is straightforward but excellent - think roast chicken and fancy mac and cheese. Just don't tell your dining mate that they charge for bread.

Cocoron review image


Japanese in Nolita


Get Directions  |   212-966-0800  |  Website

Hours: THURSDAY5:30PM to 11:00PM
    Perfect for
  • Casual Weeknight Dinner
  • Dining Solo
  • Impressing Out of Towners

Suitable For: Dinner With Ex Who Wants To Catch Up

You ran into an ex at a mutual friend's birthday party, had a nice conversation, and the next morning there's an email with the subject line "Hey" in your inbox. "We should catch up, for real some time. Dinner?" The key to surviving this? Don't make a BIG DEAL out of it. Grab some soba at Cocoron - it's warm and friendly, but not at all romantic. The interactive dipping soba will give you something to talk about other than, "How's work going" and they don't serve hard liquor, which is probably for the best. Also, it's very affordable and cash-only - you can probably both leave a $20, rather than fiddling with one of you trying to pay on a card. These are the things we think of so you don't have to.

Turntable Chicken Jazz review image

Turntable Chicken Jazz

Korean in Koreatown

Hours: THURSDAY12:00PM to 3:00AM
    Perfect for
  • Big Groups
  • Birthdays
  • Day Drinking

Suitable For: Going Out With High School Friends You Haven't Seen In Years

To make this dinner a success, the key is spending minimal time asking everyone where they're living now, and getting straight to reminiscing about the time Jeff threw up on the carpet in Allison's parents' living room. In other words, you need a place that has light-up beer towers. This fun Koreatown restaurant has those, as well as great fried chicken and other stuff to share.

Ippudo review image


Ramen in East Village


Get Directions  |   212-388-0088  |  Website

Hours: THURSDAY5:00PM to 11:30PM
    Perfect for
  • Dining Solo
  • Eating At The Bar
  • Impressing Out of Towners

Suitable For: A Good Cry

First of all, the city's best ramen shop is way easier to get into when you're alone. And you're probably alone right now. It's dark in here, and everyone's too focused on their food to pay attention to you. So let your tears drip with reckless abandon right into a bowl of rich, creamy pork broth. It'll make the soup even saltier.

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