How to make small talk, according to a barista

Chatting with strangers, acquaintances or even co-workers can feel awkward and uncomfortable if it’s something you aren’t used to. But for Jenn Wingfield, the 28-year-old head barista at Café Goodluck in Dartmouth, N.S., making small talk has become second nature.

In this instalment of Everyday Experts – a series of conversations with Canadians offering their advice on daily life – Wingfield shares her tips on the art of small talk.

How did you get into this line of work?

I used to work in the rock climbing industry, and when I moved from Toronto to Halifax in 2018, the only climbing gym at the time, Seven Bays, had a cafe in it, so I applied for a job and was cross-trained in both. I fell in love with the cafe work. I love chatting with people. It’s really, truly one of my favourite parts of my job. You’re invited into people’s lives, and you hear about what makes them excited and are with them through the hard times. When a spot at Café Goodluck opened up in 2021, I moved there. Then in 2022, I became the head barista – it’s just a fancy way of saying “assistant manager.”

Have you always found small talk easy?

Yes and no. I’ve always been a really social person, and I love being around people. But small talk was harder for me when I was younger. I actually have social anxiety, but it’s something that I’ve worked to get better at and develop tools to manage. But initiating a conversation was a hard thing for me.

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As a barista, how did you learn to initiate small talk?

I just watched and listened to one of my co-workers who was really good at it. Her two go-to questions were: “How’s your day treating you so far?” and “Do you have anything fun on the go this afternoon?” If somebody wants to chat, they’ll take it and run with it. And if they don’t, it’s an open-ended enough question that they can take an easy out.

Have those opening questions led you to interesting or unexpected places?

Absolutely, yes. I’ve had a few people across the counter share stories of loss or heartbreak. People also share fun and exciting things, like they’ve just quit their job and are going in a new direction, or they’re going on a vacation. I’ve had a fair number of regulars tell me that they’re pregnant or that they’re planning to propose or just got proposed to.

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How do you keep small talk going?

If somebody gives you a little piece of information, ask a follow-up question about it. For example, if they say they’re just going to work today, ask what they do and if they like what they’re doing. It helps to approach it with genuine curiosity because the more curious you are to know about something, the easier it will be to keep the conversation going.

How can you tell when someone is up for making small talk and when they’re not?

Their body language can be an indicator. If they’re up for it, they’ll give you a lot of eye contact, or they’ll have an expression on their face that’s more open, and it doesn’t look like they’re in a rush. Their body might be angled toward you. But if they’re turned away or not making eye contact, that’s an indication that they’re not interested in continuing the conversation. If I ask a question and they give a short answer or don’t give a ton of information, that’s also a sign that they don’t want to keep talking.

What’s your advice for someone who feels nervous about making small talk?

As a person who regularly overthinks the things that I have said in public, the best advice I’ve heard is that the other person isn’t thinking about it the way you are. What you thought was a stupid question, somebody else probably thought was really thoughtful. You can also start by practising in a lower-stakes setting, like with a barista or a grocery clerk, which makes it easier than settings that feel higher stakes, like a dinner party.

This interview has been edited and condensed.