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20+ Strategies for Avoiding (& Pivoting) Awkward Conversations

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The number one rule for avoiding awkward conversations is to never go to parties. This year, Thanksgiving is off the table.

End of article.

Don't let this happen to you. (Just kidding! Mayukh and Amanda love each other!)
Don't let this happen to you. (Just kidding! Mayukh and Amanda love each other!) Photo by Bobbi Lin

But, but, but... you’ve already planned the menu and reserved the turkey. Which is to say that some level of awkwardness is unavoidable. Buck up! Brace yourself.

(And if, you say, there is "no" awkwardness at your Thanksgiving table, you’re either taking the “intimate route”—just you plus the loved ones and pets you spend each day with and some gently flickering tealights—or you’re too blissfully oblivious to recognize it. This is a good thing! If you cannot feel the awkwardness, the awkwardness does not exist. You’ll notice that many of the relatives or guests who initiate said discomfort—in my case, great aunts and uncles and semi-strangers who mutter about politics under their breath—are the same people who are immune to it.)

One of the loveliest parts of Thanksgiving is the anyone-is-welcome mentality that brings together big groups of strangers and relatives who might as well be. But as vibrant as a conversation between an unpredictable group can be (“Oh my gosh, we went to summer camp together!”; “Oh my gosh, we’re both passionate about wild bears in the Ecuadorian mountains!”), it can also be full of uncomfortable silences, forced laughter, intent stares at super-fascinating breadcrumbs, and an exorbitant number of bathroom runs and drink refills.

21 Dinner Party Conversation Starters for Awkward Silences

21 Dinner Party Conversation Starters for Awkward Silences by Leslie Stephens

Are You For or Against Seating Plans at Dinner Parties?

Are You For or Against Seating Plans at Dinner Parties? by Lindsay-Jean Hard


In hopes of offering some relief, we're drawing on some homegrown “wisdom,” as well as our favorite tips from experts, for avoiding (and pivoting) uncomfy conversations. (And we've also got a list of questions to wake up even the most sound-asleep "discussion.")

Well, here it goes I guess...

Take precautionary measures before the meal ("dinner party homework").

As a guest:

  • People will ask you vague, hard-to-answer “What’s new?” and “How’s life?” questions that often yield no good response. So have your own stump speech. As a food writer and stylist (what's that?) in Brooklyn (how's that?), I need to spend a few minutes working on my spiel about what my life is like and what Food52 is so that I don’t end up saying “fine” when people ask me how I am or “food” when people ask me what I do.
  • Come prepared—casually prepared, not dress rehearsal prepared—with some talking points for when the silence falls: What interesting things did happen to you (or your friends, or your pets) in the past month? What are you proud of or looking forward to or grateful for? Make a list (mental is fine) on your way to the party. Include books, movies, music, events, interesting people you’ve met (or seen on the street!).
Oh, look! A couple of interesting articles to read for conversation fodder:
What Foods Does America Tweet About Most—and What Can That Tell Us?

What Foods Does America Tweet About Most—and What Can Tha... by Mayukh Sen

Madhur Jaffrey Was an Actress First—She Still Is

Madhur Jaffrey Was an Actress First—She Still Is by Mayukh Sen

  • If you know the other guests but you only see them once or twice a year, take a quick survey of where they are in their lives before you arrive (I employ my mom’s help for this; social media also comes in handy for stealth research). That’s so you don’t end up asking your 8-year-old cousin about middle school or your recently-divorced uncle about his marriage.

As a host:

  • If you’re truly fearful about bringing a group of disparate people together, start with an ice breaker (and don’t worry if it goes off the rails). This is particularly natural—as natural as ice breakers among of group of adults not at a camp or college orientation might be—on Thanksgiving, as you can go around the table and have guests express what they’re thankful for. (Last year, my family also chose to discuss our “spirit animals”—not an exercise I can recommend to you, though I did find out that my mother associates with ducks.)
  • Turn on music.
10 Playlists to Match Your Thanksgiving Vibe, From Honky-Tonk to Cali Cool
10 Playlists to Match Your Thanksgiving Vibe, From Honky-Tonk to Cali Cool

You're seated next to a guest you've never met before. Now what?

  • A conversation that never starts at all is more awkward than any unbreakable silence. If I’m seated next to a guest I don't know, even if the host forgot to introduce us (helloooo), my policy is to force myself to make the introduction right off the bat. The longer I sit next to a stranger without saying hello, the more awkward it becomes, and with every passing moment, I’m exponentially less likely to take the conversational plunge. (“I know we’ve been sitting next to each other through two courses, but hi, I’m Sarah”—no, that never happens.) Besides, there’s only so long I can talk with the familiar person to my left without the urge to turn my neck, anyhow.
  • Before you’ve introduced yourself, have an idea of what you’ll say once that initial barrier has been crossed: As Jill Isenstadt, vice president of coaching for Joyable, an online therapy program for people with social anxiety, told Real Simple, a "standby opener"—something very simple (Jill suggests "How do you know the host?")—can provide peace of mind.

    For what it’s worth, other mingling experts suggest steering away from dead-end questions in favor of those that might lead to more interesting results: Jessica Hagy, author of How to Be Interesting (in 10 Simple Steps) suggests, “How did you get here?” but some other ideas might be: What did you do for Thanksgiving last year? Did you celebrate the holiday growing up? What are you looking forward to in the next month? What do you like—or hate—about your current job?
Place cards mean you won't forget anyone's name!
Place cards mean you won't forget anyone's name! Photo by James Ransom

You're running out of things to talk about.

  • Ask more questions than you answer. “I generally enjoy conversations when the other person talks more, so I’m always asking questions,” our data analyst Sarah Yaffa told me. You’ll come across as a great conversationalist if you ask leading questions that give the other person the opportunity to chat away.
  • Speaking of the type of questions to ask, you might want to brainstorm three or four to have in your back pocket. Think about questions that are neither yes or no dead-stoppers (“Do you like cats? No?” R.I.P. conversation...) nor total stumpers that will make the other person rack his or her brain (“What are your biggest hopes and dreams?” or “What do you think about this particularly obscure person’s oeuvre?”).
  • Put questions you yourself have a hard time answering (“So how are you?” or “What’s new?”—the answer is always “everything” or “nothing”—or “Why do you look so tired?” or “Are you okay?”) in time-out for the night (or forever?), and go with those that will spark conversation and inspire stories (we've done some of this work for you): Where did you grow up? What’s your favorite thing about the city you live in? When’s the last time you belly-laughed? What’s the last article or book or TV show that made you think?
Your parties look like this, right? Mine too!
Your parties look like this, right? Mine too! Photo by Skye McAlpine

You've tried your hardest to resuscitate it, but the conversation is still half-dead.

  • Avoid addressing the awkwardness outright. I have a tendency, when faced with a vacuous silence, to go ahead and verbalize it, with a “well, this is awkward” or, more likely, a few “soooo”s and “ummm”s and “let’s see”s and “what else, what else”s. These sorts of statements make everyone—even the unflappable—acutely aware of the discomfort.
  • In following, do not “awkward turtle.” There is a reason we put this hand motion to rest back before 2010. Other hand motions—the thumbs up, the thumb-index-finger gun, and the a-okay—should not be used in excess, if at all (but this is more of a reminder to myself than a warning to you all).
  • When in doubt, compliment. Thank the host for having you. Express awe at the table settings and centerpiece.
  • When in doubt of what to compliment, compliment the food.
  • When you’ve sufficiently complimented, eat. When you’re eating, you don’t have to—and probably shouldn’t—talk.
  • Remember that the silence isn’t as bad as you think it is. It's not going on for as long as you think it is. Someone will say something soon. Better to ride it out for a bit than to blurt out something you didn't mean to verbalize.
Make slurpable ragu and no one will have to say anything at all.
Make slurpable ragu and no one will have to say anything at all. Photo by Linda Xiao

When the conversation is on the right track, maintain course.

  • It goes without saying that some topics should be avoided—be that in general or at your particular event—but just what those subjects are varies among groups. In the introduction to “The Seven Things You’re Not Supposed to Talk About” episode of This American Life, the host Sarah Koenig’s mom, Maria Matthiessen, outlines unworthy topics of conversation, which include: how you slept, your period, your health, your dreams, money, dieting and dietary restrictions, and “route talk," meaning how you got there and how trying the experience was. (But are you allowed to broach these topics with family? “I suppose so, if you want to bore your family” was Sarah’s mom’s answer.)
  • So gauge your audience. Maybe it’s a group of doctors (or political pundits) and you’re confident that you’re all on the same page. Chatter away. The goings-on in news will probably come up anyway.

Your uncle brought up [insert terribly divisive, painful topic here].

  • What if you’re discussing something that makes you uncomfortable—politics, religion, "Game of Thrones"—and you don’t know how to pivot but you’re desperate. Take a tip from Anna Sale, creator of the podcast Death, Sex & Money and a host at WNYC. She advised Real Simple readers to repeat the last thing the person said—to express that you’ve heard them—and then shift to a wildly different place: “You can also do this by gently interrupting when someone is rambling and not making a point. Wait for a break, then sum up their message for them: 'What an incredible coincidence. I'm sure that made you feel so connected in your new city.'" Then move on.
An interesting centerpiece can be the topic of conversation. Right? Right?
An interesting centerpiece can be the topic of conversation. Right? Right? Photo by James Ransom
  • When it comes to controversy, choose your battles. For many people, this is the end of a hard year. Since you might be among a group of strangers or people you rarely see for Thanksgiving, it's likely that some of their comments (and some of your comments!) might not jive with everyone's beliefs. “When a polarizing issue comes up at a party or a family gathering, let it go,” Samuel Barondes, author of Making Sense of People, told Real Simple. “Make this your mantra: It's very interesting to hear your point of view; I have a somewhat different perspective." But also, know your convictions and what you don’t put up with. You don’t have to sit idly by as a conversation that offends you takes place: Excuse yourself and go to the bathroom or to get something else you "need": a glass of water, another drink, a buttered roll.

You're trapped and you really need to get away (mentally or physically):

  • Sacrifice someone else at your table. This sounds harsh but is effective and can be necessary. Jeanne Martinet describes the technique in her book The Art of Mingling and on her blog:

    Step One) Surreptitiously look around you and locate someone you either know or have just met. (Don’t worry, if the person you are with is a bona fide Bore, he won’t notice your eyes wandering a bit.) Proximity is important; you are going to have to be able to reach out and shanghai this third person.

    Step Two) While nodding enthusiastically to what the Bore is saying, pull this new person into your twosome. Immediately you will feel a shift, a loosening of the Bore’s hold on you.

    Step Three) Introduce the sacrificial lamb to the Bore in a way that implies you are just being a good mingler by introducing two people who will probably have a lot in common.

    Step Four) As soon as their eyes meet, leave immediately; you must fade out of the conversation within twenty seconds or this substitution will not work. A pleasant 'Excuse me' will also serve as an alternative to a silent fade-out.

  • "The Human Sacrifice may sound mean to some people, but I assure you it is perfectly acceptable party protocol," writes Martinet. "You can’t be considered rude to the Bore since you have procured a new conversational partner for him before leaving. And the person you just used as the sacrifice can just as easily find his own way out, if he wants to. Remember: All’s fair in love and mingling.
  • Our Creative Director Kristen Miglore does not condone the human sacrifice move. Instead, she recommends bringing someone into the conversation who will make it easier for all three of you to find a topic to discuss together.
This does not look like the kind of party where an awkward conversation happens, but alas!
This does not look like the kind of party where an awkward conversation happens, but alas! Photo by Skye McAlpine

Recommended Questions

Infinitely better than vague "How are you?" or "How's life?," these questions offer more direction without putting your talking buddy on the spot. (Ease into them: Best not to overwhelm someone with a "Tell me your hopes and dreams and the values you hold dearest to your heart" before finding out what they do for a living or where they live.)

For total strangers:

Early in the conversation:

  • What did you do last Thanksgiving? How have you spent the holiday in the past?
  • Where did you grow up?
  • What's your favorite part of living in [insert city or town here]?
  • What do you do for a living and how did you get to that place?
  • What are your hobbies outside of work?

Later on:

  • What are you looking forward to in the next month?
  • Have you eaten at any good restaurants (or cooked anything delicious) lately?
  • What's the last good book or article you read?
  • What are you doing for the holidays? Do you have any trips or activities planned?
  • What's your best Thanksgiving memory (besides this one, talking to me, of course)?
  • When's the last time you laughed really hard?
  • Where's the best place you've traveled to?
  • If you could move to another city or country, where would you go?

For relatives who might as well be (or strangers you saw last year):

  • Last time I saw you, you were [insert craftily-researched or remembered fact here]. How's that going?
  • Are you still at the same job? What's your favorite part about it (or, what keeps you there)?
  • Remember the last time I saw you, when [insert fun memory here. Childhood memories are acceptable].
  • So you're in [insert grade in school—again, research comes in handy]. What are you learning? What are your favorite and least favorite classes?
  • Are you working on any new projects in work, school, life? What are you proudest of?
  • Are you planning to buy any gifts for the holidays? Do you need help brainstorming?
  • What Thanksgiving food have you been looking forward to the most?
  • What's the funniest thing your pet has been up to lately?
  • Did you hear about [uncontroversial, relatively well-known news story]?
  • What's something you'd like to learn more about?

And, when I'm wrapped up in asking questions, I sometimes forget the even more important part: to listen to the answers. They'll naturally lead to additional questions (and the foundation of "research" for next year's encounter).

Plus, once I get the conversational ball rolling, maybe I won't want the interaction—or the party—to end? On Thanksgiving, anything is possible.

When you find yourself in an awkward conversation, what do you do? Tell us in the comments below!

Automagic Thanksgiving Menu Maker!
Automagic Thanksgiving Menu Maker!

Tags: Entertaining, Thanksgiving, Tips & Techniques, Advice, Holiday Entertaining