How to Perfect the Art of Small Talk

Six NYC ‘experts’ offer their tips on shooting the bull

October 25, 2018 9:00 am

If you live in New York, there’s a good chance you have at some point entered a large room, snagged a cocktail and hid in the bathroom for 10-20 minutes to avoid small talk.

But eventually, we all have to come out of the stall and face the music bland conversation.

To make it (slightly) more bearable, we hit up six New Yorkers who are well-versed in the art, asking for their tips on how to open things up and knowing when to throw in the towel.

Rule no. 1: Never ask, “How are you doing?”

View this post on Instagram

A post shared by Jonathan R. Stein (@jstein6583) on

Jonathan Stein, Real Estate Agent

Always: Wait for someone to ask about what’s new with you, and remember to simplify professional and personal triumphs. No one likes an Eeyore as much as no one liked Uncle Roman in The Great Outdoors.
Never: Vent about everything that’s going wrong in your life or pull a “Hey, have any single friends who would love to meet/date/marry me?”
Good openers: “How much does a polar bear weigh? Enough to break the ice.” “So, in American Psycho, he’s just dreaming all that sh*t, right?” “Sunday go-to movie, EXCLUDING Shawshank Redemption. Go!”
How to keep it rollin’: “How’s the family doing?” (You may not know anything about their family. Hell, they may not even HAVE a family, but it’s one way to find out more about them.)
How to end it gracefully: “Let’s have coffee soon!” (Even though we probably won’t, and why would we? We just caught up!)

View this post on Instagram

A post shared by Nic Richards (@honey_knuckles) on

Nic Richards, Director of Hospitality at Classic Car Club Manhattan and seasoned barkeep veteran

Always: Listen to the other person first.
Never: Bring up uncomfortable facts about reality.
Good openers: A smile.
How to keep it rollin’: It helps to serve them alcohol.
How to end it gracefully: Walk away and keep them guessing.

Emmanuel, Lyft driver and get-me-crosstown-fast savior

Always: Ask a specific question, not “How are you doing?” It needs to be about them, something where you actually care to hear what they have to say.
Never: Talk about religion or bother them if they are crying.
Good openers: A recent news topic or a happening in the city. Never the weather.
How to keep it rollin’: Ask more questions.  
How to end it gracefully: Ask them to pay their fare!

View this post on Instagram

A post shared by riabird (@riabird) on

Ria Bird, Lead in the radical 88 Palms and nightlife hero at Rose Bar

Always: Ask about the other person! Everyone loves to talk about themselves, so the more interested you are, the more at ease they’ll feel. And be genuine! People can always tell when you’re not actually interested. Small talk is like tennis. Be ready to serve and to respond to being served. One question about you, one question about me. Keep it balanced.
Never: Get too personal too quickly. If someone does ask very personal questions, I’ll find a funny way of dodging it. As soon as people find out I’m from Utah, 80% of them ask if I grew up Mormon. I laugh it off by saying “Oh, sooo Mormon! I have seven husbands!” This gives them something to laugh about while hinting that that’s not an appropriate category for us to get into just yet.
Good openers: “Are you from ___ originally?” I love to find out where people are from, then respond to that with whatever anecdote I have about that region. I’m lucky enough to have traveled extensively and met people from many backgrounds.
How to keep it rollin’: Find something else you want to know about this person. “How did you meet our mutual friend?” “What do you think about the performance we just witnessed?” Compliment their outfit. “I love ___. Where did you get it?”  Ask yourself how you can make this person — and therefore yourself — feel more comfortable in the current situation.
How to end it gracefully: “So great chatting with you!” Let them feel like you’re doing them a favor by walking away. Making people feel important always ensures a lasting impression: “I’m going to let you get back to ____” works wonders. Even if you’re the one who has more important things to get back to.

Christina Zervanos, Founder and CEO of Christina Zervanos PR

Always: Have your Cab Franc in your thermos to make it through. Or choose your vice of choice.
Never: Share your personal social media handles in the event your small talk charm is so alluring that the conversation unnecessarily continues and you become the victim of a stalker. Also, don’t go home with a potential client and swap bodily fluids.
Good openers: I hate small talk, so tell ‘em something that matters to you. Dangerous territory, but it sucks ’em right in: “Do you have a psych rec? Mine just fired me.”
How to keep it rollin: Maintain eye contact, but keep it aloof in moments. They’ll wonder if you are flirting or high on NY’s latest magic, and it will help the encounter drag on for a solid five minutes.
How to end it gracefully: “You’ve been so refreshing to talk to in such a vapid world … but my self-medicating tendencies require more cab franc from a straw … in my bed … whilst reading the uplifting poetry of Sylvia Plath. Goodnight.”

View this post on Instagram

A post shared by Velvetina Taylor (@velvetinataylor) on

Velvetina Taylor, Burlesque Entertainer

Always: Express genuine enthusiasm. “I’m so excited about …” “Have I told you about …” “Didn’t you love …?”
Never: Wait for the other person to make you feel comfortable.
Good openers: See first response, but also find common interests and set them up to elaborate on their experience.
How to keep it rollin’: Share something personal, but not depressing. Make an authentic connection without oversharing.
How to end it gracefully: Express gratitude for their time and admit to whatever it is you’re excusing yourself to do, be it getting a drink, seeing someone you know, leaving, looking at something else or whatever strikes you.

Main image: imdb

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.