How to Small Talk if You Hate Small Talk


Because the holidays don’t seem to stop even after the holidays, we’re re-sharing this 2016 story on how to make small talk if you hate small talk. It pairs especially well with a tall glass of bubbly and a napkin full of pigs-in-a-blanket.

I have two speeds when it comes to small talk: “Tell me your life story!” or a nice, blank stare. It depends on my mood, how much I’ve had to drink and how much work I’ve just left behind on my desk. I consider myself a friendly person and yet, a very large part of me frequently forgets how to speak English. I also suspect I’ve become more awkward as I’ve gotten older. The nice thing is that I’m not alone. I know this because of conversations with friends and non-conversations with those who also suck at shooting the shit, where we both just stood there like ____________ …. ________ k bye!

But just because we’re bad at something doesn’t mean we have to stay stuck. Old dogs can learn new tricks. I asked a small talk expert, the founder of Bumble, the Head of Community at dating app The League, an etiquette coach, and two entrepreneurs who frequently put small talk into habit for their tips.


Rosalie Maggio, nicest person I have ever spoken to on the phone, is the author The Art of Talking to Anyone. The first thing she told me is that we’re all better at small talk than we think, and to remember that everyone feels bad at it. “Consider the smooth talkers on television and in the movies,” she said. “Those people have labored long and hard over their lines.” For those of us who aren’t thespians with a script in hand, Maggio has a four-part system:

1. Make statements.
2. Then ask questions.
3. Offer a piece of information about yourself. “I was born in Texas,” or whatever.
4. Ask something personal about the other person, then start over.

Vary these, don’t do all of the talking and ask questions but don’t interrogate. Listen and respond.

Katie Schloss is a designer and Social Media Consultant who I met because she introduced herself to me. We had a mutual friend, then learned we had more, and it was she who kept the conversation going. (I was very brain dead, she made it easy.) She honed her chatting skills while working at trunk shows where she had to strike up a conversation with every potential customer.

She has one major go-to, and one big thing she avoids. She starts conversations with people she doesn’t know by offering a compliment. “It opens people up,” she says. As for the big no: She never asks people what they do for a living. “It puts someone in a box and labels them.” Instead, Schloss asks questions like, “What do you care about right now?” Or, “How do you spend a day?”

Myka Meier, Founder of Beaumont Etiquette, also suggested opening with a compliment. “The most charming people in the world are brilliant small talkers,” she said. “They evoke positive emotions in people. That’s all charm is.” The key is to keep the compliment genuine. She agreed with Schloss’ no career-talk sentiment, unless you’re at a work function. “From an etiquette perspective it seems opportunistic,” she said. “You might as well ask, ‘How much money are you making?’ Don’t do that either.”


Katie Shea, co-founder of Slate NYC, moderates a monthly breakfast of startup executives. She was right there with Schloss in terms of no-work talk, but added that sometimes the deeper questions you want to ask don’t always land. “Context is important, she said. “Know your audience. If someone’s not responding, go back to something easy like, ‘‘What’s your favorite restaurant?’” Make it an open-ended question that can’t be answered with one word (the ultimate conversation killer) by adding a follow up such as, “And what do you like about it?”

This follow up is equally important — if not more so — when it comes to online small talk. Most popular dating apps require some chit-chatting. How else are you going to give or get someone’s number?

Meredith Davis, Head of Community at The League, coached me on the steps that come before the digit exchange. (You know, asking for a friend.) “If you’re going to make the first move, reach out with that person’s name,” she said. Then ask a question pertaining to his or her profile using clues from the bio and photos. For example, “I saw you were at XYZ band’s concert, I love them. What were they like live?”

I told her that for as much as I dislike small talk in person, I physically cannot do it over text or on apps. I come across as very robotic and then overcompensate with exclamation points. “That can be your funny thing,” she told me. Say, “Listen, I’m really witty in person but not so much on here, as an FYI.” There’s no need to fake it or perform, in other words. Just, you know, get words going.


Whitney Wolfe, founder of Bumble, the dating app where women have to make the first move for conversation to begin*, told me that Bumble is in the process of building out new product features to encourage deeper, less small-talk-y conversation. “It’s awkward to dive into politics or culture intensely, but imagine if we prompted that,” she said. “You don’t swing your racket unless a ball is coming at you, but what if we threw the ball? Maybe you’d swing your racket.” As someone who doesn’t understand how to discuss the weather, this is way more up my ally. Love in 2017!

She still agreed that small talk is important, unfortunately. “Small talk breaks the ice, and we want to mimic real life. You’d never go up to a stranger in a coffee shop and ask about their thoughts on long-term relationships.”

(Me: Oh?)

She’s also all for sending an emoji if you can’t think of anything to say. “It works,” she told me of enough people who’ve shown her proof.

Okay. We’re now far enough into this story that we have a few tricks in our back pocket. Make connections using information offered and ask people questions like, “How do you spend your day?” Offer compliments to break the ice. No asking about jobs right away. No interrogating, and no asking questions that can be answered with a one-word dead end. What else?

From Myka Meier on the in-person approach: Don’t discuss vices, always have a drink in your hand (it doesn’t have to be alcoholic — having a drink in your hand signals that you’re here to be social) and don’t show up late. “If you show up after 40 minutes, people will have already paired off,” she told me. That said, if this happens and you need to break in, choose someone standing alone or with one other person, max (much easier than entering groups of three or more, Myka says) and channel all that you’ve learned above.


If you’re really terrified, remember the words of Rosalie Maggio. “Just walk up to someone where people are gathered and say, ‘I’m so glad to be here.’ It sounds inane, but people will soon forget your first sentence. They are far more likely to remember your last sentence, or that you listened.”

And if someone doesn’t respond? Every individual I spoke with promised that in person, this rarely happens. Everyone is looking for someone else to say hi, to start the conversation and help keep it going. As for that guy who just went dark on Bumble, Whitney Wolfe says that you can always throw out the old emoji. “Send him the cricket. Call it out. You have to give people something to work with.”

What a mouthful, huh?

*When your settings are set as a woman looking for a man, or a man looking for a woman. The conversation is fair game when women are matched with women and men with men.

Photos by Krista Anna Lewis

Excellent at talking but scared to have The Talk? You’re not alone. You know who’s excellent at DTR-ing? Prince Harry. What about crying at work? Wanna talk about that?

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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