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How to make playground small talk less painful

“It’s so nice your kid’s hair is brushed. I could barely get pants on mine.”
Collage of two moms mouths smiling with talking bubbles on a yellow background
Consider starting a small talk sesh with another parent by giving a compliment (whether or not it's genuine).Tyler Essary / TODAY Illustration / Getty Images

Spending hours at the playground is a rite of passage and an almost-daily ritual for many parents … as is making awkward conversation with others who are in the same boat. 

But fast-talking mamas Jessica St. Clair and Casey Wilson are using their conversational superpowers to help you elevate your playground chitchat with their new audiobook, “The Art of Small Talk.”

"Casey and I declared ourselves self-appointed masters of small talk and we decided to teach some of our tips and tricks," St. Clair tells

These best friends experienced "failure to thrive" during Covid because they missed the "sizzle" of interacting with strangers, St. Clair says. "We didn't realize how much dopamine and joy we were getting from our small talk until it was ripped away from us."

The seed for the audiobook was planted when St. Clair discussed small talk with Wilson on her podcast, "The Deep Dive." St. Clair says her co-host, June Diane Raphael, "was unfortunately not receptive to our message, but a lot of our listeners were." So the duo "heeded a call — that our friends tell us nobody has made — to bring our only skill and talent to this world and teach people how to small talk."

"And the rest is history," adds Wilson.

In the delightfully narrated audiobook, St. Clair and Wilson share six simple steps to boost your small talk game. You can find descriptions of those steps in this essay by Samantha Mann.

As a self-proclaimed hater of small talk, I decided that I might benefit from a listen, and for me, the major takeaways for general small talk are:

  • Focus on small talk as an opportunity, not an obstacle. The dopamine hit you get from interacting IRL is legit, according to research that audiobook contributor Malcolm Gladwell "forced" St. Clair and Wilson to do.
  • Use the weather to your advantage. Sure, it's not a riveting topic, but it is a great starting point.
  • Ignore any potential small talk fails you may experience and keep on trucking. St. Clair says that her father (who appears on the audiobook) insists that the secret to recovery is knowing that people are thinking more about whether they have lettuce in their teeth than they are about whatever error you made.
  • Starting an interaction with a compliment is a great way to go. "It's a pleasantry. It's kind of like greasing the wheels," Wilson says. Of course you want to aim for completely authentic praise, but "occasionally a genuine compliment might not pop up, and at that point you might look to see what's meaningful to them." After all, even if someone is wearing "a completely tragic brooch," St. Clair says, remember that "the brooch is in the eye of the beholder."
  • Small talk can get you out of conversations. Wilson has adopted audiobook contributor Amy Poehler's advice to "establish the fact that you do have to go before you start talking to someone. Because then you're not making them feel badly when you walk off." Props like headphones or an empty wine glass can be your best friends when you need a reason to exit the chat.

Small talk at the playground

Rules and guidelines are all well and good, but I wanted to know what small talk looks like in practice, especially for exhausted, overwhelmed, just-trying-to-get-through-the-day parents. Luckily, St. Clair and Wilson were game to share their best openers.

Here, St. Clair interjects a word of caution: “If you are the type of parent that has an emergency safety kit in your purse, don’t take it out unless I ask you for a Band-Aid. We need to go forward like we are a mess because that makes people feel comfortable.” Tapping into common commiserations “is what’s going to get you more of a connection in a park-like scenario.”


Every week at the playground, Wilson says she turns to the mom next to her and says, "The dads seem so proud of themselves when they show up at the park on a Sunday, don't they?"

"Someone should give them a medal. A lifetime-achievement award for showing up," adds St. Clair.

Fascinating facts

St. Clair's park go-to is: "You know what I read? In Paris, they always have a café that serves alcohol at their parks. Can you imagine how much more pleasant this would be with a glass of rosé in your hand?"

She also suggests a riff on the theme: "In Europe, you don't have to play with your kids. You can just sit quietly and read a book." 

Old faithful

For the more straightforward among us, St. Clair suggests the solid, "Do you live near here?" or "Do you come here a lot?"

Like talking about the weather, it's not revolutionary, but it works, rain or shine.

Physical gestures

The pair suggests using a "Mona Lisa smile," which St. Clair describes as "a tiny upturn on the sides of your mouth" rather than "a full-teeth smile." This may serve as an invitation to have someone else begin small talking with you.

Wilson sometimes gives other parents of young children an eyeroll that says, “Here we are, existing in parenting together, and I’m doing a bad job and I am in this with you.”

Kid compliments

"I always find you can have a genuine compliment to someone's kid because you can just say, 'Oh, she's so cute,' says Wilson. "To me, that's just the perfect opener. You can be completely genuine in saying it ... most of the time."

When St. Clair sees a child with gorgeous hair, she might say, "God, I want that blonde. Could I snip a lock and bring it in to my colorist?" You can also compliment both the parent and child by saying, "She has your eyes!"

On the flip side, St. Clair reminds you of the self-deprecating option: "It's so nice your kid's hair is brushed. I could barely get pants on mine."

Get straight to the point

Wilson suggests being honest and saying, "You seem to have it together and be a nice, normal person."

"'How do you do it?'" St. Clair adds. "And then they'll say, 'Oh, please, I'm not.' And then you're bonding."

Listening to feedback

Through their studies in small talk, self-described extroverts St. Clair and Wilson have actually learned that they may need to do more listening.

"That was a tough pill to swallow for Casey and I," admits St. Clair. "So I've been trying to do a little less talking and a little more listening. But not too much listening because, c'mon, we're the experts here."