How to Start a Conversation — and Why It Matters More Than You Think

Seven simple lessons for making first conversations easier and more meaningful

The Accidental Expert

Debra Fine never set out to become an expert in conversation.

In fact, for much of her early life, she avoided it. As an overweight, bookish child, she sat silent at the back of classrooms, convinced that others were born knowing how to make friends — and that she had somehow missed the lesson. Later, as a young engineer, she found a career where technical skill mattered more than small talk. It was safer that way. At conferences and industry events, she perfected the art of arriving late, leaving early, and hoping someone else would start the conversation first.

It wasn’t until a pivotal night — standing across a room from a man exchanging shy glances — that something shifted. Urged on by a friend, she took a deep breath, walked over, and said hello. That one small risk, she later realized, changed everything.

Debra discovered that small talk isn’t trivial — it’s the gateway to real connection. She taught herself how conversations work, step by step, and then began teaching others. Published twenty years ago, The Fine Art of Small Talk was her answer to the millions of people who were never taught either: a guide to making the first move, starting a real conversation, and opening the doors we otherwise leave closed.

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After a few weeks of exploring personality and compatibility, today’s newsletter veers in a slightly different but closely connected direction: conversations — and in particular, the very first conversations we have with people we don’t yet know.

Last week, I introduced Wayvelength, a simple tool that helps two people find a point of connection based on aspects of their personalities they have in common — like both being quietly introverted, or both being highly responsible and conscientious. The app then gives them a personalized icebreaker question to help start their conversation.

It made me realize: if we’re giving people a spark to connect, it makes sense to also learn more about how to help that first conversation flow. That’s why I picked up Debra Fine’s book. It’s full of practical advice for easing those first few minutes of meeting someone new.

Here are seven of her key ideas that stood out to me.

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Seven Fine Lessons for the Art of Small Talk

1. Replace childhood warnings with adult habits

Old advice like “Don’t talk to strangers” served us well when we were five. As adults, it’s self-defeating. In safe settings, talking to strangers is how new friendships, opportunities, and experiences begin.

2. Take responsibility for introducing yourself

Waiting to be introduced is a losing game. Hosts are busy, and most people are too shy themselves. Be proactive: smile, extend your hand, say your name — and you’ll often be the most memorable person in the room.

3. Silence isn’t golden — it’s risky

Shyness can easily be mistaken for arrogance or aloofness. Staying silent sends a message whether you intend it to or not. Make the effort to speak, even a little — it’s often seen as friendliness and confidence.

4. You’re not the only one who feels awkward

At almost any event, nearly everyone hopes someone else will start the conversation. If you break the ice first, you’re doing others a favor. Most people will be relieved and grateful rather than critical.

5. Start small: a smile, eye contact, and hello

Conversation doesn’t have to start with a witty remark. Practice smiling at people and saying a simple hello. It builds the muscle of approachability and makes bigger conversations much easier.

6. Use people’s names — and give your own

Remembering and using someone’s name makes them feel valued — it’s a quiet superpower. If you forget a name, admit it with grace. And when you meet someone, always offer your own name too — even if you think they should remember it.

7. Keep a few icebreaker questions in your pocket

Debra Fine recommends having a handful of easy, engaging questions ready for when conversations stall. Icebreakers don’t have to be brilliant — just inviting.

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Excellent advice, I think — and speaking of icebreaker questions, Wayvelength is coming together nicely.

Everyone I’ve shared the idea with so far has been enthusiastic — not just about the concept, but about the real need it addresses.

Last Wednesday evening, I was at an event in San Francisco. Although I wasn’t using Wayvelength (yet!), I ended up meeting four or five new people — and in most cases, we found something in common. One conversation even uncovered that we had both been at the same Quantified Self conference in Mountain View back in 2011, years before I moved to the US.

I came away from the evening feeling really energized — not just by the individual conversations, but by the bigger reminder: meeting new people can be exciting and meaningful if we can just lower the barriers a little. Take away the awkwardness. Make it easier to find common ground.

Wayvelength has an important job to do.

And days like Wednesday make me even more certain it’s worth doing.

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P.S. If you’ve had a great first conversation with someone lately — or a small moment of connection that surprised you — I’d love to hear your story.