How to Talk About Awkward Things

In a recent Saturday Night Live sketch called “Dinner Discussion,” a group of friends is happily dining together, when one of them brings up an op-ed in the New York Times—“the one about Aziz Ansari.” In response, the table falls silent. Beck Bennett shrinks into his turtleneck. At one point, Aidy Bryant cuts off her own hair. Anything to cause a distraction, anything to not have to actually have this conversation.

While writing my new book about the psychology of awkwardness, I’ve been interested to note how many people and organizations exist that argue we need to have more of these kinds of uncomfortable conversations. There is Living Room Conversations and Village Square, both of which help people facilitate talks among friends or acquaintances about subjects like money, mental health, and the environment. There’s also Hi from the Other Side and the American Dialogue Project, both of which connect people of different political persuasions for a short phone chat, accompanied by a trained facilitator.

“Awkward” can feel too inconsequential a word to apply to such serious subjects as political polarization and mental health. And yet activists and commentators have adopted the term to encourage more dialogue about taboo subjects. Earlier this year, a PSA called “Seize the Awkward” debuted, which encourages young people to talk to their friends who they suspect may be struggling with mental health. Last year, journalist Ana Marie Cox launched a new podcast, With Friends Like These, which she has often described as being devoted to awkward conversations. On one episode of that show, Cox interviewed the comedian W. Kamau Bell, who has for years encouraged Americans to have more so-called awkward conversations, which for him are typically discussions of consequential but sensitive subjects like racism or sexism.

That’s a lot of people counting on the power of awkward conversations to change minds. But are they right? And if you want to have a conversation like the ones encouraged by these groups—where do you even begin?

The short, maddeningly inconclusive answer to the first question: Maybe it works? So far, the best research draws on two well-established ideas in social psychology. One of them is perspective-taking, or the ability to imagine and then feel what someone else is feeling. The second is active processing, a term that means abandoning your gut instinct in favor of carefully thinking something through. More specifically, there seems to be something special in combining these two concepts, something that takes people from shallow arguments based on gut instincts toward real understanding and empathy, maybe even compassion.

And yet awkward conversations can be so distressing. I know myself, and I know that if I get into a conversation about something huge and uncomfortable with someone who sees the issue differently than I do, my mind will go blank, and more often than not, I’ll say nothing. I’m not sure how much muttering jargony words to myself (Active processing!!) would help me when I’m feeling nervous.

It’s tough, because in some ways, this is far too complex to be explained with some kind of prescriptive rule book. But some social psychologists, like Alana Conner at Stanford, are at least trying to give people a place to start. Conner is the executive director of SPARQ, a Stanford think tank that seeks to apply social science to the real world. (Its mission is in its name: Social Psychological Answers to Real-World Questions.) “The first step is actually not to try and persuade anybody,” she tells me. Instead, approach the conversation like an anthropologist: Try to understand, to the best of your ability, how this person sees the world. It’s a cooler, calmer way to talk about difficult subjects.

Also: Ask questions, particularly ones that start with the word “why.” This serves the dual purposes of helping you better see the world from another person’s point of view and giving you something to say when words are failing you. And Conner encourages people to use “I” statements as often as possible: When you say X, I feel Y. This way, it becomes less about throwing facts at each other, or, as Conner put it, it’s less about “me trying to beat you into submission with my fact stick.” Instead, she said, it changes “the discourse to ‘We are two people who care enough about each other to see why we disagree.’”

The unfortunate truth is that you can’t just do this once and expect immediate change. You’re going to have to keep having these talks. I interviewed W. Kamau Bell for my book, and he told me that despite his own conviction about the importance of awkward conversations, it’s not that simple. “I’ve heard this from people: ‘Kamau, I listened to you about the awkward conversations, and I tried to talk to my grandfather once, and it was so bad, it didn’t work, so I don’t agree with you anymore!’” he said. “Like, who are you to think once is going to help?”

I mentioned earlier how the word “awkward” can feel too slight to be applied to heavier subjects, but I’ve started to wonder whether that’s to our benefit. Maybe using the word can make the discomfort feel more manageable, perhaps especially for those of us who are not naturally bold. It’s just a little awkward. That’s all. “For me, leaning into the awkwardness and facing the fact that it’s going to be awkward makes it clear that that doesn’t mean bad,” Bell said. “It just means ‘Okay, I’m going to feel uncomfortable and embarrassed,’ and not naming those things as negative. That’s just part of an awkward conversation.”

Excerpted from CRINGEWORTHY: A Theory of Awkwardness by Melissa Dahl. Copyright © 2018 by Melissa Dahl. With permission from the publisher, Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. All rights reserved.

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