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The Elevate Edit by Alison Cheperdak · Aug 22, 2026

Consider This Your Small Talk Refresher

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Alison M. Cheperdak · The Elevate Edit by Alison Cheperdak

There’s something about September that has a very different cadence to it than summer.

Whether you or your family are in your back-to-school era or heading back to Bible study, book club, regular work hours, school events, volunteer meetings, or whatever else makes the fall feel booked and busy, September tends to bring us back into the world a little bit.

The out-of-office replies start disappearing. Summer Fridays come to an end. Meetings return to the calendar. Weekends that revolved around travel are replaced by dinners, fundraisers, conferences, school functions, sports practices, and all the other things we somehow agreed to do this fall.

And after a summer when many of us spent most of our social time with people we already know and like, we’re suddenly going to be doing considerably more talking to acquaintances, colleagues, other parents, friends of friends, and complete strangers.

Consider this your small talk refresher.

I’ve always been a defender of small talk. It sometimes gets dismissed as shallow or pointless, but I think that misunderstands what it’s for. Small talk isn’t supposed to be the most interesting conversation you have all night. It’s the bridge that gets you there.

It’s how strangers become acquaintances, how new colleagues begin to feel comfortable around each other, and how you figure out whether the person standing next to you at a cocktail party also happens to love the same obscure book, vacation spot, restaurant, sport, or artist that you do.

But like most social skills, it gets easier when you use it regularly. If yours feel a little rusty after summer, here are a few ideas worth remembering.

One of the easiest ways to become better at conversation is to stop expecting yourself to invent it entirely on the spot.

I had a hilarious law professor who I wrongly assumed shared original material with each of his classes. When I got access to old lectures in preparation for exams, I realized his classes were more of a collection of well-timed greatest hits. He shared the same stories, the same jokes, and the same perfectly delivered lines, and I don’t blame him! It’s no wonder he also has a flourishing career as a legal contributor on TV.

Similarly, before walking into an event, have two or three things in mind that you would genuinely enjoy discussing. A book you just finished. A trip you took this summer. A restaurant you loved. Something interesting happening in your city. A television show you’re watching. A funny, noncontroversial story you recently read.

You’re not preparing a script. You’re simply giving yourself somewhere to go when someone inevitably asks, “What’s new?”

And while we’re here: “Nothing much” is almost never the most helpful answer.

Give people something they can work with.

Below are a few of my favorite questions because they are specific enough without feeling like a deposition or a quiz with just one right answer.

“What was the best thing you did this summer?”

“Have you read anything good lately?”

“Do you have anything you’re looking forward to this fall?”

“How do you know the host?”

“What have you been working on lately?”

The goal isn’t to have a collection of clever questions memorized. It’s to ask something you’re actually interested in hearing the answer to.

People can usually tell the difference.

Being a good conversationalist does not mean conducting an interview.

If you ask someone where they went this summer and they tell you about Maine, you can certainly ask a follow-up question. But you can also offer something about yourself.

“I love Maine. We used to go when I was younger.”

“I’ve never been, but it’s been on my list forever.”

“I was just talking to someone about how beautiful it is there in September.”

Good conversation has some back-and-forth to it. Ask. Listen. Offer. Repeat.

People give us conversational openings constantly.

They mention that their daughter just started college. They tell you they recently moved. They say they’re training for a marathon, starting a new job, renovating their kitchen, or heading to Italy next month.

You don’t need to come up with an entirely new subject. Pick up the thread they just handed you.

“How is she liking college?”

“What made you choose that neighborhood?”

“Is this your first marathon?”

“Where in Italy are you going?”

The best conversationalists aren’t necessarily the people with the most interesting stories. Often, they’re simply the people who are paying attention.

A few seconds of quiet can feel much longer when you’re standing with someone you’ve just met.

It’s also worth knowing that speaking more slowly and pausing before you answer a question often comes across as more thoughtful. We may feel awkward in the moment, but others are more likely to perceive your pause more positively or not notice at all.

This one may be the hardest after summer.

When you’re standing alone at an event, your phone offers the world’s easiest escape hatch. You can suddenly become extremely interested in an email you had no intention of answering until tomorrow.

Try not to.

Looking around the room, making eye contact, smiling at someone nearby, or simply standing there without appearing occupied makes it so much easier for someone to approach you.

And sometimes being approachable is half the work.

You don’t need a dazzling opening line.

Talk about the room. The food. How you know the host. The speaker you just heard. The neighborhood. The event. The beautiful flowers sitting three feet away from both of you.

We sometimes make small talk harder because we’re trying so desperately not to sound like we’re making small talk.

This may be the most important refresher of all.

When people feel nervous socially, they tend to focus inward: What should I say? Do I sound interesting? Was that awkward? What does this person think of me?

Try replacing some of those questions with a different one:

How can I make this person feel more comfortable?

Small talk gets much easier when you stop treating it like a performance.

Sometime in the next few weeks, you’re probably going to walk into a room where you don’t know everyone.

Before you do, put your phone away. Think of three things you’d be happy to talk about and three things you’d genuinely like to ask someone else.

Then go say hello first.

Your social muscles will remember what to do.

Q: I started a small interior design business a few years ago that has since grown into my full-time job. When I was catching up with an acquaintance recently, she asked about it and then said, “Do you actually make money doing that?” I think she was genuinely curious and not trying to be rude, but I had no idea how to answer. I didn’t want to discuss my income, but I also didn’t want to make it sound like my business is just a hobby. What would you have said?

A: You can correct the assumption without answering the question.

I’d probably smile and say something like, “I do it full time now, and I’ve been really fortunate with how much the business has grown.” Then I’d move the conversation toward something I’m comfortable discussing: a recent project, a new employee, an exciting client, or what I enjoy most about the work.

You don’t owe anyone an income statement simply because they asked, but you also don’t need to pretend you aren’t proud of building a successful business in an effort to make the other person feel comfortable.

I’d also give your acquaintance a little grace. “Do you actually make money doing that?” is certainly more direct than I would recommend, but she may have been genuinely curious about how an interior design business works rather than trying to diminish what you’ve accomplished.

For the rest of us, this is a good reminder that curiosity doesn’t entitle us to someone else’s financial information. If you’re interested in a friend’s unconventional or entrepreneurial career, try: “How has the business changed since you started?” You’ll probably learn more anyway.

If you have a question for a future Answering for a Friend segment or my Ask Alison column, please email info@elevateetiquette.com.

For more writing like this, my modern etiquette guide, Was it Something I Said?, is on sale wherever books are sold.

With love,

Alison

Read the original on alisoncheperdak.substack.com

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