There is a very specific moment that happens when you want to talk to someone.
You notice them. Maybe they seem interesting. Maybe they’re attractive. Maybe there’s just something about them that makes you curious.
And then your brain immediately asks the most important question imaginable.
What the hell am I supposed to say?
Suddenly, saying hello feels like a complicated social experiment.
You consider making a joke. Too risky.
You consider asking a question. Too interview-y.
You consider complimenting them. Too obvious.
You consider doing absolutely nothing.
Much safer.
So you do nothing.
And five minutes later, they’re gone.
The frustrating part is that you probably weren’t actually bad at conversation. You just tried to figure out what the conversation would be like before you had it.
That’s an important distinction.
We aren’t particularly good at predicting what happens when we talk to other people. We can underestimate how much we will learn from conversations with strangers, and we can also underestimate how enjoyable those conversations might be once they actually begin.
In other words, your brain may be doing a terrible job of selling you on something you might actually enjoy.
So let’s talk about how to start a conversation.
Not with a list of twenty-seven supposedly irresistible opening lines. Just how to make talking to another human being feel a little less like an audition.
Why Does Talking to a Stranger Feel So Much Harder Than It Is?
The problem starts before you ever open your mouth.
You’re trying to predict the outcome. Will they like me? Will I sound awkward? Will they think I’m bothering them? What if I run out of things to say? What if there’s an uncomfortable silence?
What if they give you that look that says, very clearly, please go away?
Your brain is essentially trying to write the entire screenplay before filming the first scene.
Of course that’s intimidating.
And there’s something else happening too. When you’re nervous, you tend to focus on yourself. How you’re standing. What your face is doing. Whether you’re talking too much. Whether you’re talking too little. Whether that sentence made any sense.
Meanwhile, the other person is probably doing some version of the exact same thing.
They’re wondering how they are coming across.
That’s one reason conversations can feel much more threatening from inside your own head than they actually look from the outside.
The first goal, then, isn’t confidence.
It’s simply getting out of your own way long enough to say something.
You May Be More Likable Than You Think
This is one of the more comforting things to remember when you’re nervous around new people.
After conversations with other people, we often underestimate how much our conversation partners actually liked us and enjoyed talking with us.
Think about how often you’ve walked away from a conversation thinking something like Well, that was awkward.
Meanwhile, the other person may have walked away thinking, They were really nice. I hope I see them again.
You don’t know.
That’s the point.
You are guessing, and your guess isn’t necessarily accurate.
This matters enormously when you’re trying to meet people.
If you assume someone won’t like you, you’re less likely to approach them. If you don’t approach them, you never get any information that might prove your assumption wrong.
You can end up protecting yourself from rejection by making sure you never give connection a chance.
That’s a pretty lousy bargain.
You Don’t Need an Interesting Thing to Say
This might be the biggest myth about conversation.
We think interesting people say interesting things, so before approaching someone, we start looking for an interesting thing to say.
The problem is that interesting conversation doesn’t necessarily come from an interesting opening. It comes from what two people do with whatever they start talking about.
You don’t need to know whether the person has an incredible life story. You don’t even need to know whether they’re particularly interesting.
You need to find out.
That’s actually the fun part.
You don’t know what the conversation will become.
That’s not a flaw.
That’s the reason to have it.
Start With Whatever Is Already Happening
The easiest conversation starter is often the thing sitting directly in front of you.
You’re at a party, so ask how they know the host. You’re waiting in line, so make a comment about the line. You’re at a concert, so ask whether they’ve seen the band before. You’re at a class, so ask how long they’ve been doing it.
You’re at a coffee shop. You can literally talk about the coffee shop.
It doesn’t have to be brilliant.
“Have you been here before?”
“Do you know what this place is like?”
“Is that actually good?”
“Do you know when this starts?”
These are not going to win any awards for literary achievement.
They don’t have to.
They’re openings.
That’s all.
The mistake is thinking your first sentence needs to be memorable. It doesn’t. It just needs to give the other person somewhere to respond.
Ask Something You Actually Want to Know
Questions are useful, but there’s a difference between asking questions and conducting an interview.
You don’t want to fire off a list of questions that makes the other person wonder whether they’re applying for a mortgage.
Instead, listen for something you genuinely want to know more about.
If they mention a trip, ask about the trip. If they mention a hobby, ask how they got into it. If they mention a restaurant, ask what they ordered. If they mention a job they clearly love, ask what they enjoy about it.
There is a very simple reason this works.
People can tell when you’re listening.
And being listened to feels good.
You don’t have to impress someone when you can simply be interested in them.
Follow the Thread
This is where good conversations become much easier.
Someone says something. Instead of immediately jumping to a completely new subject, follow it.
They say they just got back from New York. Ask what they liked.
They say they loved the food. Ask where they ate.
They mention a tiny restaurant you have never heard of. Now you’re talking about restaurants.
Maybe they tell you they found it through a friend. Now you’re talking about their friends.
Maybe that leads to where they grew up. Now you’re talking about where they came from.
You didn’t prepare any of those subjects.
The conversation created them.
That’s why you don’t need a mental database of conversation starters. You need to listen to the answer you just received.
It sounds obvious.
It is.
And yet when we’re nervous, we often listen only long enough to figure out what we’re going to say next.
Try not doing that.
Let the conversation take a turn.
It might surprise you.
Stop Trying So Hard to Be Interesting
This is probably the most counterintuitive advice in the whole article.
Stop trying to be interesting.
Not completely. You should still have a personality. But you don’t need to constantly prove that you have one.
A good conversation isn’t a performance where one person entertains the other. It’s an exchange.
You say something. They respond. You respond to that. They ask you something. You tell them.
You disagree about something. You laugh about something. You discover you both have a weird obsession with the same television show.
That’s conversation.
You don’t need to walk away thinking, Wow, I really crushed that.
In fact, if you’re spending the entire conversation evaluating your performance, you’re probably not experiencing much of it.
The goal isn’t to impress them.
It’s to find out whether you enjoy each other.
That’s a much more useful test.
What If the Topic Is Completely Boring?
Here’s something I love about conversation. People can be surprisingly bad at predicting whether a conversation will be enjoyable.
We look at a subject and decide it’s boring.
But a topic isn’t having the conversation.
People are.
You could have an incredibly interesting conversation about someone’s commute. Or their dog. Or the sandwich they just ordered. Or why they hate their neighborhood. Or why they absolutely love their neighborhood.
The subject is just the doorway.
What matters is what you find once you walk through it.
So don’t panic because the person you’re talking to said something ordinary.
Ordinary is fine.
Ask another question. Offer your own opinion. Tell a little story.
See where it goes.
What If You Say Something Awkward?
You probably will.
At some point.
Congratulations. You’re human.
You might make a joke that doesn’t land. You might forget someone’s name approximately four seconds after they tell you. You might say something that comes out differently than it sounded in your head.
You might have a weird little silence.
None of these things automatically ruins anything.
One of the problems with being nervous is that you assign enormous importance to tiny mistakes.
You think the other person noticed your awkward sentence as intensely as you did.
They probably didn’t.
And even if they did, so what?
Sometimes a little awkwardness actually makes people more comfortable because it makes the interaction feel human.
Perfect people are exhausting anyway.
What If They Don’t Want to Talk?
This is the part that deserves to be said clearly.
Sometimes someone isn’t interested.
That’s okay.
They might be busy. They might be tired. They might be in a relationship. They might be having a terrible day. They might simply not feel like talking.
Or they might just not be interested in talking to you.
It happens.
A short answer is information. So is someone repeatedly looking away, giving minimal responses or making it clear they want to leave.
Don’t push.
You don’t need to turn every interaction into a negotiation.
A simple “Nice talking to you” is enough.
And here’s the important part.
Their lack of interest doesn’t prove you did anything wrong.
It proves that two people did not happen to want the same interaction at that particular moment.
That’s dating.
That’s life.
A Conversation Doesn’t Have to Become a Date
This is where we put a little of the pressure back on the floor.
You don’t have to approach someone because you have already decided they’re attractive enough to potentially date.
You can just talk to them.
Maybe they’re interesting. Maybe you have something in common. Maybe you become friends. Maybe you flirt. Maybe you discover there is absolutely no romantic chemistry whatsoever.
All of those outcomes are perfectly fine.
One conversation doesn’t need to justify itself by producing a phone number.
Sometimes the point is simply meeting another person.
And oddly enough, removing the pressure to get something out of the interaction can make it much easier to connect.
You’re no longer thinking, Do they like me?
You’re thinking, Who is this person?
That’s a much better question.
When You Actually Like Someone, Your Brain Gets Dramatic
Of course, all of this becomes considerably harder when you’re attracted to the person.
Suddenly the stakes feel higher.
You become very aware of your hands. Your voice sounds strange. You forget every interesting fact you’ve ever learned.
Someone asks what you like to do for fun and your mind produces absolutely nothing.
You like dogs. You have hobbies. You’ve traveled. You have opinions. You’ve had a whole life.
And somehow, at this exact moment, you are a blank sheet of paper.
Take a breath.
You don’t need to reveal your entire personality in the first five minutes.
You don’t need to make them fall for you.
You don’t even need to know whether you like them yet.
Just talk.
Ask something. Listen. Answer something honestly. Let them see a little bit of you.
The whole point of dating is discovering whether two people like being around each other.
You can’t discover that without actually being around each other.
Curiosity Is More Useful Than Confidence
We talk about confidence constantly in dating.
Be confident. Walk confidently. Make eye contact. Don’t be afraid of rejection.
All useful advice, to a point.
But curiosity might be more useful.
Confidence says, I hope they like me.
Curiosity says, I wonder who they are.
That’s a completely different mental position.
One puts you on trial.
The other makes you an explorer.
If you’re curious, a boring answer doesn’t necessarily end the conversation. It becomes another question.
You’re not desperately trying to keep things alive.
You’re genuinely looking for something interesting.
That tends to show.
You Might Learn More Than You Expect
There is another reason to talk to people that has nothing to do with dating.
Everyone knows something you don’t.
That sounds obvious, but we rarely behave as though we believe it.
The person sitting next to you has had experiences you haven’t had. They have met people you haven’t met. They have made mistakes you haven’t made. They know places you don’t know.
They may have an entirely different way of looking at something you thought you understood.
That alone is a pretty good reason to start talking.
You may walk away with a restaurant recommendation. A new idea. A funny story. A different perspective. A reason to visit somewhere.
Or simply a reminder that the world contains far more interesting people than the ones already in your phone.
That’s not nothing.
The Person You Almost Didn’t Talk To
Think about how many people you have seen in your life and never spoken to.
The person at the party. The person at the gym. The guy at the coffee shop. The woman standing next to you at the concert.
The person you kept making eye contact with but never approached.
Maybe nothing would have happened.
Probably, most of the time, nothing would have happened.
But you don’t actually know.
That’s the strange thing about avoided conversations.
You get no evidence.
You don’t find out that they were boring. You don’t find out that they were delightful. You don’t find out that you had nothing in common.
You don’t find out that they were secretly hoping you would say hello.
You simply leave with the question.
And the human brain is very good at filling unanswered questions with whatever story makes the most sense at the time.
Usually, we make the story about ourselves.
They probably wouldn’t have been interested.
Maybe.
But maybe not.
You Don’t Need a Better Opening Line
If you’ve been waiting for the perfect conversation starter, I’m going to disappoint you.
There isn’t one.
You can say something incredibly clever to someone who doesn’t want to talk and get nowhere.
You can say something completely ordinary to someone who is interested and end up talking for two hours.
The sentence matters less than we think.
The person matters. The timing matters. The mutual interest matters. And what happens after the opening matters enormously.
So instead of trying to memorize the perfect thing to say, give yourself a few simple rules.
Notice something.
Ask about it.
Listen to the answer.
Follow the thread.
Share something about yourself.
Pay attention to whether the other person is meeting you halfway.
That’s it.
No secret formula. No conversational magic trick. No pickup artist nonsense required.
Maybe You Were Never Bad at Conversation
Maybe you just expected too much from the first ten seconds.
You thought you needed chemistry immediately. You thought you needed a fascinating topic. You thought the other person was judging you.
You thought a little awkwardness meant the conversation was failing.
You thought you needed to know where the conversation was going before you started it.
But that’s not how conversations work.
They’re unpredictable.
That’s part of what makes them interesting.
You don’t need to know what the conversation will contain before you have it.
And maybe that’s the part worth remembering the next time you see someone you want to talk to.
You don’t have to know what happens next.
You just have to be willing to find out.
You Only Have to Say Hello
There is a strange amount of courage involved in doing something incredibly ordinary.
Walking over.
Saying hi.
Asking a question.
Starting a conversation.
Not because the moment is guaranteed to become something important.
It probably won’t.
Most conversations don’t.
But every friendship, relationship, flirtation, romance and unexpected connection starts with people who did not yet know where the interaction was going.
That’s the part we forget.
You don’t need to know whether someone is going to like you before you talk to them.
You don’t need to know whether you’re going to have chemistry.
You don’t need to know whether you’ll have anything in common.
You don’t even need to know what you’re going to say five minutes from now.
You just need the first sentence.
After that, you have something you didn’t have before.
A person to respond to.
A conversation that’s actually happening.
And maybe, occasionally, something neither of you expected.
So the next time your brain starts giving you ten excellent reasons not to talk to someone, remember that your brain is trying to predict a conversation that hasn’t happened yet.
It might be wrong.
You won’t know until you say hello.