Casey Wilson and Jessica St. Clair Have Mastered the Art of Small Talking

In January 2022, Casey Wilson was a guest on The Deep Dive, a podcast hosted by her longtime friends and frequent comedy collaborators June Diane Raphael and Jessica St. Clair. The episode kicked off what the pod was calling their Lifelong Learners Series, an only moderately satirical moniker for their discussions dedicated to everything from tablescaping to mixology; Wilson — known for her highly popular Real Housewives-centric podcast Bitch Sesh — was enlisted to discuss what they called The Art of Small Talk. She and St. Clair, both professed experts in chit-chat, riffed about their favorite places to approach strangers (in line at Home Goods, in an elevator) and offered a few of their well-weathered tips (keeping it light, pivoting away from so-called energy vampires).

“The response to that specific episode was pretty wild and I got all sorts of DMs from people saying they wished it was longer, that they secretly wanted to learn more about how to small talk,” says St. Clair. “It birthed the idea to do a full audiobook. In the shadows, people wanted to hear about this, so we heeded that call.” What came of it is The Art of Small Talk, an eight-hour audiobook from Malcom Gladwell’s Pushkin Industries, that expands on the original premise — with scientific research, expert interviews, celebrity guest spots and, of course, chit chat. Ahead of the audiobook’s May 7 release, and a promotional tour that Wilson admitted is poised to put their love of chat to the ultimate test, the authors spoke to The Hollywood Reporter about all things gab.

***

You’re still in the early stages of the book tour, but how are you feeling as two self-expressed extroverts?

JESSICA ST. CLAIR Some people work with people who aren’t their best friends, but for us, I’m actually really excited. I will be in my jammies, tucked in with Casey, having late night fries. But we’re going to be small talking with the true professionals, on television, and although we consider ourselves masters we can always learn something. We’re lifelong learners.

CASEY WILSON We never said we were perfect — we did say we were pretty much perfect, but we’re going to amend that. I was recently on the Today show and I had to go toe-to-toe with Hoda Kotb!

Did you learn anything from Hoda and Jenna [Bush Hager]?

WILSON I will say, they surprised me in saying they hate small talk. I had to say: Ladies, this is your job and you’re the best in the biz, what are you talking about? They seemed a little taken aback that that’s what I considered their job to be (laughs).

Something I’ve always wanted to know about that sort of live television is, are you chit-chatting with the hosts right up until you go live, the way you would in another interview format?

WILSON Yes. Some hosts, who shall remain nameless, will go a little dead inside in between segments. I don’t blame them one bit, because of the amount of energy you need to perform at that level. But not Hoda and Jenna, they’re so lovely when the camera is off.

ST. CLAIR Steve Harvey is an amazing small-talker. When I went on Celebrity Family Feud I thought we had, I’m not going to say a sexual connection, but I thought he was really into me. Then once the lights went down he was — poof! — off on his helicopter. He has to bow out as soon as he’s done. But I appreciate those boundaries, and that’s something we talk about in the book. You have to know when to let the right one in.

As podcasters, how do you square the desire to be constantly listening to one’s podcasting friends while out running errands with the desire to be ready to small talk with anyone you might run into? What do we do about the AirPod of it all?

WILSON I only listen to my podcasts when I’m doing things around the house, I have to be available when I’m out. I am great at pulling one headphone down and still getting a joke off. If someone’s washing their car, I’ll pull one side down and be like, “do mine next,” and then the headphone’s right back in and I keep on rolling. That’s more of a drive-by small talk where you don’t need a response.

ST. CLAIR We’re pretty aggressive in the book about saying we want those ear buds out, especially when you’re walking the dog or checking out at the grocery store. There might be angels walking amongst us. I know that’s a bridge too far for some people, but you just don’t know what you might be missing in terms of dopamine hits. Every positive interaction with a stranger gives your body a jolt. Unless the podcast you’re listening to is one of ours, then keep your ear buds in please. But if you can just do one interaction a day, it’s a gateway drug. We recommend just the tip, and then you’re going to want more.

WILSON And I use my standard lines a thousand times. I have no shame in that. You’re in an elevator, you go, “oh, I never know what buttons to press!”

ST. CLAIR If it feels like we’re stopping at every floor I like to say, “well, looks like we’re taking the local!”

WILSON If you’re just starting out, use a compliment because it’s easy and a nice entry. Once you compliment somebody they might give you a little nugget back. Like, “oh, I got this brooch in Albuquerque.” Then you say, “oh, the Southwest, I’ve always wanted to visit.”

ST. CLAIR Or, “I hope topaz comes back!”

WILSON Even if you hate that city and would never wear that broach.

ST. CLAIR That brings us to our next rule, which is to lie. That’s a controversial one, and we’ve had some pushback from friends when they hear how much we lie during our daily small talk. But the lies help grease the wheels. If someone next to you pulls out a Tom Clancy book and asks if you’ve read it, if you say, “I hate Tom Clancy,” then end of scene. We’re trying to “Yes, And” these interactions. And also, make that person the expert in whatever you’re talking about, even if it’s brooch-wearing. Even the most boring-seeming person has a passion for something. And once you get that nugget, you can add it to your toolkit. You just put it in your little satchel and swing it over your shoulder like a hobo on your way to the next whistle stop on your train journey.

WILSON And, at the very least, you can commiserate with the next person about how boring that story was. Like, “God, that story about the brooch almost killed me.” A lot of these rules will move together. I love how you’ve barely been able to ask a question and we’re off…

Well this banter made me think of a situation-specific question. You both live in L.A., so how do you handle small talk with celebrities? What if there’s a famous person in, say, a random elevator with you?

WILSON That’s a tricky situation. It’s not always a safe space for that. I sort of go the opposite way with a celebrity, which is that I don’t say shit and that’s my opening. Everyone else is trying to get something going with them and then they appreciate my normalcy. My silence is my small talk. It’s communicating: I don’t need anything from you and I respect your boundaries.

You tapped some celebs from your own circle to do interviews and offer advice in the book. I want to talk about how you chose those folks, but first I’m curious about Colin Quinn.

ST. CLAIR Colin Quinn is the funniest and sexiest man alive. I hope you understand that.

WILSON He gives off his gems the way a Real Housewife does Cameos — they’re just in the shower or walking down the street and you’re along for the ride. Colin was doing his thing, and we’re just sitting back and getting pearls of wisdom. The result was that the quality of the audio maybe leaves one wanting (laughs), but he certainly does not.

ST. CLAIR He gave me my first job in television. I’d never been on a set before and I’ve never felt more taken care of in my life. First thing, he asks me, “do you want a Snapple?” Next thing you know, we’re on the street buying one from a souvlaki man and he’s chatting with me. He’ll talk to anybody and make them feel welcome.

Did you have a wish list of sorts when it came to the other contributors?

ST. CLAIR Tony Hale is a master and also a dear friend, so we knew we wanted him. And we really went after Amy Poehler because her small talk changed my life. I was interning at UCB, I had a terrible haircut and was wearing capri pants that my calves were too big for. I didn’t think I was cut out for this, I was having trouble breaking in and there weren’t many women there at the time. One day on her way out of the theater, Amy just stopped me and said, “hey, what’s your name?” She said, “thank you so much for helping out here, we really appreciate it.” That’s all it took, and I was like okay I’ll devote the rest of my life to comedy.

WILSON She’s great with her own small-talking boundaries that are always at the forefront of her mind. Perhaps because she is a celebrity, but she strikes me as someone who loves to interact but is mindful of not being taken advantage of, or getting into an energy leakage situation where she’s spending an hour with someone she passes on the street.

ST. CLAIR She has a structure to her small talk — like her tip for being on an airplane is that she takes her headphones out and then has a little bit of rapport with the person next to her, says like, “oh, is the chicken good? maybe I’ll get the chicken.” And then she says, “okay, back to my podcast!”

I’m having a hard time imagining Amy Poehler in anything less than a Delta One pod.

ST. CLAIR Oh, people can get to you anywhere. They’ll creep over a partition like a little meerkat.

WILSON That’s why I like that technique of having a prop, like Amy and her headphones on the plane. I know we’re contradicting ourselves because we said earlier we don’t want you wearing them.

ST. CLAIR Casey has really taken on the idea of having a glass in your hand at a party. So you can be on your way to the bar if you need to get out of a conversational jam.

WILSON You’re always on your way to the bar. But you’re not doing what some people might think to do, which is midway through a conversation go, “I think I need a drink.” Instead what you’re doing is searching with your eyes — where is the bar? — and then you can go up to the person on your way to finding the bar. You’re doing a bit of theater. The person, and the conversation with then, is a beautiful way station on your route. But that way you don’t get trapped, and you can use the natural hustle and bustle of the party to drift away from the person like the end of Titanic.

I believe you said this on an episode of your podcast, Jessica, that the two of you improv-ed the whole audiobook before writing it as a script and then performing from that script?

ST. CLAIR This is also how I work with my writing partner Lennon Parham. Casey and I talked it out and recorded ourselves, and then wrote from there. It was crazy because at first we thought, how much do we really have to say? And it turns out quite a lot. We had like 10 hours.

WILSON I’m sure you have no problem believing that based on this interview.

ST. CLAIR And then we also added research. We were hoping that most of it could come from TikTok’s we’d seen, but I guess because [Pushkin founder] Malcolm Gladwell’s our boss they do require that we cite some sources.

Your podcast listeners would feel I was remiss if I didn’t ask about what it’s been like for your co-hosts, Danielle Schneider and June Diane Raphael, while you guys teamed up on this.

WILSON Listen, they’re jealous. And we’ve had to give tough feedback to both of them about their own small-talk skills. I don’t mean to get astrological but —

No, please do.

WILSON They’re both Capricorns. I’d love to do a follow-up chapter about which signs are most suited for this. Leos would be the number one small talker. Capricorns are workhorses, so it’s like, “can you just stop for one second to chat?” And the answer is no. Jessica and I are the opposite, we can’t get anywhere on time because we’re stopping.

ST. CLAIR I mean, this book was two years in the making. Don’t ask us to do a sequel, because we’ll be dead by the time it comes out. Danielle and June did say to us, “now all your tricks are going to be out there, so what’s going to happen?” Listen, like Casey said, it’s jealousy. It’s not a good color on either of them. But we’re going to do an event all together in L.A. so we can get into it there. And I’ll point out that June likes to small talk in a vacation setting, which is the one place we won’t do it.

WILSON She’ll do it in a hot tub. Talk about being trapped. You’re in Hawaii for the next six days with these psychopaths. But we do applaud that.

ST. CLAIR I had a friend who small talked in a hot tub and a few days later she had an invitation to swing. An invitation she didn’t want to have. They had to hide from them at the buffet every morning.

What is coming up that you are most excited about?

ST. CLAIR We’re going on Drew Barrymore’s show and I’ve got to tell you, I love her interview style. I just love how she touches and crawls up on people like a little cat. I hope she touches me.

WILSON I’m really excited. She’s somebody who really uses her gift for small talk to uplift and bring joy. It’s like her mission. When she got that show it was like oh, that’s why you were put on this Earth. It’s the big leagues of chatting.