How to start a conversation

Death of Small Talk
6 days ago
5 min read

Updated: 4 days ago

5 minute read

Starting a conversation is one of those things that sounds simple, looks easy when other people do it, and feels almost physically impossible when it's your turn.

If you're reading this, you're probably not stuck mid-conversation. You're stuck before it even starts, searching for the perfect thing to say, or talking yourself out of it before it happens. And that's not a you problem. Nobody ever taught you this stuff.

We've run live events for thousands of people, built a conversation app, and even landed in The Times. So we've learnt a few things along the way. Unlike the endless listicles promising 100 tips you'll never use, here are the five things that will actually help you start a conversation, Number one is a game changer. You'll see why when you get there.

Before the Conversation: Getting Your Head Right

Most conversation advice skips straight to the tips. But if your head isn't in the right place, no opener in the world will save you. Your new mindset, your new super power.

A women feeling confident after a workshop on "how to start a conversation".

5. Let Go of Perfect

The biggest block isn't shyness. It's the hunt for the perfect opener. There isn't one. Think about the last conversation that actually meant something to you. We bet it didn't start with something clever. It started with something real, something obvious, something that just came out. The magic wasn't in the opener. It was in everything that came after it.

S0, say the thing. The obvious thing, the slightly clunky thing, the thing you'd normally talk yourself out of. Real always lands better than rehearsed.

"In a University of Chicago study , commuters who started conversations with strangers on trains and buses reported a more positive experience than those who sat in silence, despite predicting beforehand that talking would be awkward"

The problem was never the conversation. It was the story we told ourselves before it started.”

4. They Already Like You More Than You Think

Here's the thing nobody tells you before you walk into a room, the version of you that shows up, slightly nervous, not quite sure what to say, is almost always better received than you think.

There's a name for this. The liking gap, the difference between how much you think someone liked talking to you, and how much they actually did. Studies of strangers in brief conversations show the same thing every time: people consistently underestimate how much they were liked. And the shyer the person, the bigger that gap.

So the next time you're talking yourself out of starting a conversation remember, it's probably going to go better than you think. It might even be one you remember for years.

How to Start a Conversation: The First Move

We've all seen those TikToks right? Someone walks down a busy street handing out compliments to every person they pass, their dog included. Great energy. Wholesome content. But I'm guessing that's not why you're here, because a compliment thrown at a moving stranger isn't a conversation. It's a drive-by. What you're after is something that actually lands, sticks, and goes somewhere.

Here's how.

Three guys laughing at a "how to start a conversation" workshop led by Death of Small Talk

3. Open With What's Actually There, AUTHENTICALLY

So now that we're confident about approaching the conversation, what do we say?

The best conversation starter is already right in front of you, the room, the moment, the thing you're both actually in together. You don't need to manufacture anything. You just need to notice what's already there and be honest about your reaction to it.

If someone's wearing the Pokémon hoodie that gives you a buzz, or the band tee of a gig you were at last year, call it. "oh, that's so cool" their wearing it, your buzzing, its a no brainer.

Let's take a harder scenario. You're feeling awkward, you don't know anyone, and there's that one person who seems completely at ease, working the room like they were born for it. Say it. "You look so comfortable talking to everyone, what's your secret?" It's a genuine observation, it's a real question, and nobody has ever been offended by being told they seem confident.

Don't go looking for something to say. Let something find you.

2. Go deeper

So, you're comfortable, you sparked a talk, now lets make it land! The follow-up is everything. One real question that goes deeper beats ten surface level ones.

First answer: "I'm a nurse." Follow-up: "What made you go into it?" Now you're somewhere. Next layer: "Has there ever been a moment that really stayed with you?" Now you're in a real conversation.

That's where the meaning lives, in the depth. Most people never go there because it feels too personal, too much. It generally isn't. People want to be asked why they made the choices they made. Ask it and you stop being a stranger almost immediately.

Follow the thread they give you. If they light up on something, go there. If something genuinely interests you, ask more. And if they're not feeling it, read the room, keep it light, move on. No big deal.

What actually Makes a Conversation Land (yes, backed by Harvard)

The single piece of feedback we hear more than anything else, the reason a conversation didn't land?

"They just talked about themselves."

Not bad people. Just people who never made the shift from performing to actually being curious about the human in front of them. That shift is the whole thing.

"In a Harvard study, the people rated most likeable in a conversation asked the most follow-up questions. Not the wittiest. Not the most confident. The most curious."

2 ladies connecting deeply and learning how to have a conversation

1. Be genuinely interested in them

All of this, the openers, the follow-ups, letting go of perfect, showing up as yourself, is just scaffolding for the thing underneath: genuine curiosity about another person.

When you're actually interested in someone, it shows in everything. The questions you ask. The things you follow up on. The way you lean slightly forward without realising you're doing it.

Start the conversation. Messy, imperfect, slightly awkward, it doesn't matter. They're probably keener to talk to you than you think. Just be interested in them, in their “WHYS”, in their story.

The worst that happens is it goes nowhere. The best? You have one of those conversations you think about for years. That's worth saying hello for.

We write about this stuff because we know how powerful one conversation can be. The right one, with the right person, can change everything.

We're building a library of blogs for you, covering everything from "questions to ask on a first date" to "how to have better conversations", check them out here.

If you want to know more about the movement, find out more here.