The Awkward Dinner Guide

Some dinners in life are going to be awkward. We’re here to help.
The Awkward Dinner Guide image

We all have those meals we look forward to. Maybe your best friends from college are in town and you know things are going to get crazy, or you’re at your favorite restaurant in the world with the one person you love the most.

But for every meal that you hope never ends, there are at least two of them that you wish would never happen. It’s an unavoidable part of life: sometimes you have to deal with weird groupings of people in uncomfortable situations that drag on forever. It’s awkward. Very, very awkward. But there is one aspect of these meals that you can control: the restaurant. Here are 14 great options for life’s most awkward meals. Stay strong out there.

The Spots

photo credit: Holly Liss


West Hollywood

$$$$Perfect For:Big GroupsBusiness MealsOutdoor/Patio SituationPeople WatchingSee And Be SeenVegetarians


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Perfect For: When your ex wants to introduce you to her new husband.

Your ex is just back from eloping in Tulum, and now you have to meet Wolf (her husband) and figure out this dog co-parenting thing. Wolf is vegan and you’re going to need some very strong drinks, so Gracias Madre is the logical answer. You can sit on the patio, and hopefully be on your third margarita by the time Wolf starts to go in deep on how cutting dairy really cleaned out his gut.

Perfect For: Dining with a friend of a friend who wants to get into the ‘industry.’

Another day, another person coming out of the woodwork who has decided that being an accountant isn’t for them: they’re destined to be a screenwriter. As the token Hollywood person in your group, you get to take the recovering number cruncher to dinner and tell them everything you know. Who cares if you’re only in the mailroom and have no actual advice - just take them to Cecconi’s, point out all the agents, and get the accountant to pay for the lobster spaghetti.

Perfect For: Dinner with your roommate (who you hate) and his parents.

It’s been five months, which is four and a half months longer than you needed to realize you hate the roommate who turned out to be an amateur-who-thinks-he’s-a-professional drummer. And despite dropping your most extreme excuses (you’re going out of town for a funeral), he’s insisting that he’s told his parents all about you and that you all have to have dinner. Admit defeat and suggest C&O Trattoria. Mr. and Mrs. Johnson will be happy with the beach-adjacent location and the garlic knots, and you can brainstorm ways to transport sand from Venice to the inside of his bass drum.

Islands Restaurant


Perfect For: Dining when you both know the relationship is over.

At this point, things are so toxic, neither of you knows who to blame for what anymore. But you’re hungry and kind of want a burger with teriyaki sauce dumped on top of it. Get to your nearest Islands for passable times and burgers with no less than 10 toppings on them. Your waitress will definitely make eyes at you, which will feel good in the moment, but suddenly you can’t find your girlfriend, and you realize you’re taking an Uber home.

Perfect For: Debuting a terrible haircut.

Your hairdresser came at you with a weedwacker this morning, and your public engagement options are limited. Good news - Jones might be the darkest restaurant in Los Angeles. The Italian spot on the Weho/Hollywood border has solid cocktails, a cool crowd, good food, and maybe the best dessert in town with that apple pie skillet. And who knows, maybe the box cut spiked up in front will be all rage thanks to you.

Perfect for: Catching up with that blogger friend who InstaStorys the entire meal.

Is there a worse sentence in the English language than “Wait, I just need to take a boomerang before you start eating”? Probably yes, but that one is still right up there. Next time you’re seeing Jade (she’s no longer Jane because “It wasn’t good for my brand”), be prepared and meet her at Croft Alley. She’ll be happy with the string light-covered courtyard and rustic wood tables, and you can order a not-at-all-photogenic cauliflower grilled cheese and be able to eat it immediately.

Perfect For: Meeting your mom’s new life partner Jean.

Your mom’s 61 years old and finally living her truest life. You couldn’t be happier for her. But now comes the part where you meet the person she left your dad for and you need pancakes. And biscuits. And every other kind of breakfast food in the vicinity. Luckily, John O’Groats is ready for you. The Westside staple has a homey interior ideal for talking, reminiscing, and learning all about Jean’s impressive arrowhead collection.

Perfect For: Lunch with that relative who just moved to LA.

Your aunt’s brother-in-law’s cousin’s kid has just moved to LA to “figure his sh*t out,” and turns out you’re the only person within 100 miles he knows. So obviously he wants to be friends. Give him a sampling of the best (eating at the end of a pier) and worst (PCH traffic) of LA life with lunch at Malibu Farm Cafe. The simple but tasty food comes out quickly (so you can make a quick exit if necessary), and Randy will probably start wondering out loud whether he should live out here in Malibu. Just nod and let him figure that one out himself.

Perfect For: Confronting your boyfriend about his affair.

It’s time to face facts and tell him you know everything. But let’s do this with a bang: get a table at Rustic Canyon and ask for a quiet corner. Order the most expensive bottle of wine and all the food you can think of, put the hammer down on him, and then leave (maybe with that bottle of wine in hand). On the scale of things, sticking him with the bill is the most polite of all possible reactions.

This spot is Permanently Closed.

Perfect For: Telling your roommate that you’re in love with them.

He’s your best friend. You guys have been through everything together, even that one time you beat him in Mario Kart 43 times in a row. But recently, you’ve realized your feelings might not be so platonic, and you need to tell him in a neutral zone. Go to your joint-favorite bar down the street, Village Idiot, for a relaxed atmosphere, some potato pie, and lots and lots and lots of IPAs.

Perfect For: Meeting your biological dad for the first time.

It’s taken you fifteen years to track him down, but there he was, hanging out in the Midwest this whole time. Now he’s coming to LA and you have zero idea how to handle this now that it’s actually happening. Don’t sign up for cable just so you can watch Lifetime movies that might give you some answers. Do have dinner at Osteria La Buca. This Melrose staple has a number of advantages: he probably likes Italian food, it’s quiet enough, and you can sit in a corner with your back to the room so no one sees your family drama play out.

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