How to Small Talk if You Hate Small Talk

From the founder of Bumble to an etiquette coach


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?

Get more Mixed Bag ?
  • OH you know what you need to do next “How to Talk on the Phone if you HATE Talking on the Phone” cuz…itme. I’m hopeless.

    • I second this!

    • Elva Lexa

      yes !!

    • Rachel Maria

      Agreed! I’m a teacher…my students say things like “hey man” to women. I can only say so much. Help!

    • I DESPISE talking on the phone.

  • Lindsay D

    I think I’m getting more awkward with age too !! Glad I’m not the only one.

  • tmm16

    I have an addiction to overthinking, so yes, I naturally dislike small talk. I’ve found that dating and going to little networking events has helped me a little (also alcohol, whoops.) I liked Rosalie’s comment that “everyone feels bad at it,” because it’s true, we all think we are awkward and get anxiety when faced with striking up conversations with strangers. If you feel this way, I think this perception though shows you are self-aware, which I don’t think is a bad quality to possess. You can be #foreverawkward, but I think it’s always a great idea to break out of your comfort zone as well!

  • Ally Mijol

    Oh my god I definitely feel so awkward these days since I graduated. This post really helped and was very charming in itself. 🙂

  • Such an interesting read. I really struggle with small talk and this was so useful – bookmarking to come back to in times of doubt

    – Natalie

  • Emma J.

    the benefit of working with really old, demented people is they don’t even remember the last thing you said, and they tend to say the same things over and over again, which means i can practice my small talk by having the same conversation slightly altered every time i talk with one of them. i know it sounds horrible but it proves useful.

    • Ciccollina

      I don’t think it’s horrible at all Emma. I used to visit my granny every Sunday where we’d drink tea and have the same conversations over and over and honestly, the joy that my company brought her outweighed every other thing. You are doing something worthwhile, I promise.

  • Not Constantinople

    Embrace the “awkward silences”. As an American expat in various countries for the last 10 years, I’ve realized that it’s only Americans that can’t abide any silences in conversation. I’ve had to ride that out and accept it.

    • Ciccollina

      So so true. I’m an Australian living in Germany and have noticed that the American / Australian habit of saying “So what do you do?” is also very much frowned upon in Europe.

      • I like that, and wish that were the case in America. I like my job and what I do, and people generally tend to find it cool, but as soon as I tell them what I do I think that people generally don’t know what to talk about anymore because I’m in an industry where not many people know anything about it and then the conversation stops, even if I keep asking them questions. My coworker experiences the same thing, and we think a lot of people either assume we’re too nerdy to carry on normal conversations, or (and I don’t want to come across as arrogant), they don’t feel as intellectually “matched” to us and get insecure.

        • Poires Poires

          ….I’m now really curious to know, What do you do?

          • I’m a regulatory specialist in the hydropower sector.

          • Poires Poires

            …well damn, lol. That sounds official as ffffff.

          • Pun intended, I hope! Yeah, it’s one of those jobs where it immediately sounds too nerdy to discuss any further!

  • Néo Bourgeois — Christum
  • Ciccollina

    Sometimes I feel like MR is tracking my brainwaves because you literally put up an article for everything I’m thinking the day after I’m thinking it. I am terrible at small talk and have always accepted it as my thing, but recently I have been in situations where I’ve felt, for lack of better words, daft, and that I cannot accept! Sadly, my #1 worst social trait is not knowing how to speak to men that are much older and more powerful than me. I would love to know how other young women address that.

    • John

      Well I’m a man, but I have found that, when talking casually to older, more powerful men (of which there are very many in my profession), it’s a good tactic to offer some very general personal interest and then just ask them what corresponding interest they have.

      For example, most people open with some variation of “How was your weekend?” or something that just asks what you’ve been up to. I’d say something like, “Oh, it was good. I saw a band. Do you ever go see music? What kind do you like?” and then they’ll go on for 20 minutes about how great the Rolling Stones are. The important thing is to keep your side general enough that you’re really just setting them up to talk about what they love. If you say, “Oh, I saw 21 Pilots this weekend” or “I binge-watched Orange Is the New Black,” they’ll have no idea what you’re talking about and probably feel a little alienated. That’s a conversation killer. So keep it basic. Just mention generally that you’re reading a good book, that you’re going out to dinner, that you’re taking a trip, and then ask “Have you read anything good lately?/Do you have a favorite restaurant around here?/What was the last vacation you took?” and they’ll give you an earful. Just act interested as hell in whatever they say and ask what makes whatever they like so great. I think music is the safest opener because not everyone is big on movies, sports, books, food….but pretty much everyone has some interest in music. Vacations are good too, because everyone takes them (or has a dream destination to which they’ve never been) and everyone loves to talk about them.

      Good luck!

      • Ciccollina

        Thank you for the thoughtful reply John! God, it’s so refreshing to have a man reply to me on the internet without trolling me. I will take your suggestions and give them a whirl in the New Year 🙂 Thanks again!

  • For me with small talk there are some instances when I’m on and can talk to anyone about anything and other times when I’m as interesting as a pet rock (a fad in the 70’s where people bought rocks as pets for real, but hey it was the 70s). I’ve just come to accept that I never know when my small talk muse will strike. A libation avec alcohol usually loosens the old lips as well.

  • Jam Jam

    Hm, ‘no interrogating’ is a good one–I like to listen, so I’ll ask a lot of questions, but it makes sense that other people want to listen to what YOU have to say, too!
    Unless you’re a born n’ bred Californian, we just want to yack about our inner child 😉

  • Erica Kan

    One of my answers for an ideal date on Hinge is, “Good food, music, and drinks with zero small talk.” Recently, a match commented and replied, “What do you enjoy talking about when first meeting someone?” This really got me thinking that every introduction with a new face is going to involve some type of small talk. Bookmarking this page!!!