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Can you get better at small talk? Here's what happened when I tried to

“What’s your recurring nightmare?” is apparently not a great way to start a conversation. 
collage of random mouths talking on a lined background
A new audiobook, “The Art of Small Talk,” suggests that small talk is a skill we can teach ourselves. TODAY Illustration / Getty Images

Small talk has been a pain point for me for years, but it sank to new lows at the beginning of the COVID-19 pandemic. I was at the playground one day, sweating in a K-95 while pushing my maskless 1-year-old on a swing. In an attempt to maintain social distance the city has tied up every other swing, rendering them out of order. 

“It’s insane all the grown-ups wear masks but pretend like the babies are fine without them, right?” I say to a mom two swings over. She nods but doesn’t make eye contact. 

As someone with a chronic mumble, I figure I didn’t speak up. “Having our babies maskless could be dangerous, right?” I shout again. The mom continues nodding without glancing my way. While it’s likely part of this fumble was related to COVID anxieties, I mentally conclude this exact type of exchange is why attempts at small talk are worthless. No one is willing to go deep — people only want to engage in elementary pleasantries. While I outwardly declare small talk frivolous, I do have the desire to connect more and feel frustrated by my incompetence.  

My grandmother, Regina, was the queen of small talk. She never left a room without a new friend or dinner invitation. For years I thought the effusiveness others regarded her with was due to her beauty, which no doubt helped, but as I aged, I realized that Regina was a professional in the art of small talk. At the playground that day, I thought about how my grandmother would have been able to make this mom smile and laugh within seconds.

I’m not the worst small talker. I have an aura that draws in strangers to ask me about directions or make note of the weather. At best, I can sustain a steady volley for 2-3 exchanges, but once the conversation quiets for a mere second, I panic and abandon ship. I’ve literally turned my back away from a person without any goodbye pleasantries. How disorienting this must be! As COVID precautions waned, like many of us, I craved more connections, but I felt unsteady. 

While trying to figure out the new social normal post-pandemic, I turned to “The Art of Small Talk,” a new audiobook by Casey Wilson and Jessica St. Clair to see if they could help me fulfill my bloodline right as a small talk queen. Right away, Wilson and Clair’s warmth and humor toward the subject made me feel taken care of. Early on, they provide a salve to a common fear: People will think I’m annoying if I talk to them. They recount research that shows people usually like us more than we think. They also make it clear that small talk is a skill we can learn, not something that's dependent on personality. I found this comforting. 

The audiobook shares six simple steps to increase confidence and ability to get better at small talk:

Always be scanning

  • Be thoughtful about who you are going to attempt small talk with. Search for a friendly face, someone with a clear similarity to yourself.

Compliments, questions and commiserations

  • Giving compliments, asking questions and low-level commiserations — about the weather or long lines, for example — are the best places to start small talk. 

Lie

  • It’s OK to give a well-meaning but inaccurate compliment, or to feign interest in a sport that you despise for the intent of sustaining and maintaining your new connection.

Place your mark in a position of power

  • Invite them to talk about themselves, their hobbies and interests.

Small talk = start shallow

  • Your goal is to connect on the banal parts of living, not discuss politics or religion. 

Don’t overthink it

  • If there’s a hurricane outside your window, talk about the weather; if there’s a huge line at Starbucks, start there.

As I listened to the rules of small talk, my fatal flaws were illuminated: I had assumed small talk was for me, when according to our experts, small talk is most effectively deployed when you think about it as a “lift” for another person. With that reframing in mind, the idea of lying (a little) was more palatable. 

But keeping small talk small was the toughest rule for me. As a personal essayist, I often forget that other people aren’t naturally inclined to open up their scabs to show others as a means of connection. And while I do have a genuine interest in the internal lives of strangers, that does not mean people want to share with me. I often ask too-serious questions in my compulsion to go deep. A few failed bids for connection? “What’s your recurring nightmare?” “Do you think women can ever fully heal our negative relationships to food?” “I heard the only way for straight women to parent equally is through divorce.” No wonder parents slink away from me at birthday parties

With a new understanding of small talk, I nervously set out to try my new skills. The audiobook reminds listeners that those working in customer service work well as marks — they’re literally paid to be nice to you — so as a practice target I close in on my barista. Before I even ask for my drink, I lob a compliment — “I love your sneakers” — which, in this case, was sincere. He seems pleased and tells me about how he bought them off Facebook Marketplace, which transitions us into a brief back-and-forth about how the kids in our neighborhood have more expensive sneakers than most adults! The small talk feels breezy and upbeat. Before I leave, latte in hand, I gesture toward the man in the back screaming about business on his phone and comment about the rudeness of people talking loudly and acting important. My barista rolls his eyes in agreement and laughs, and I’m on my way! A success from my usual bland “hi-thank you-bye.”

Since practicing my small talk, a teenager I met on the subway has explained to me the difference between crocheting and knitting, and even recommended which store has the best yarn. No, I don’t have interest in learning or visiting said store, but this kid was thrilled to show off her talent! My biggest accomplishment has been transforming a meager “good morning” to a daily chitchat with a dad I see at school drop-off. We began bonding over ragging on our preschoolers and have since moved further into the deep end of exchanges, talking about ways we believe we’re failing as parents. By sticking to the protocol of keeping it light and jointly commiserating, the conversation naturally evolved and I ended up getting what I wanted: having a near stranger tell me wildly personal information about his life.

It’s still nerve-racking to make small talk, but I assume this will get easier with practice. What I found most helpful was changing my perspective that small talk is a gain for myself to it being a lift for someone else. Each time I’ve tried, even with missteps, I’ve left an interaction feeling more connected and with a spring in my step. And that is something we can all use.