Your Roadmap
To The First 60 Seconds
Of Engaging Conversation

Today my friend Pete from Beard Strokings is going to teach you exactly what to say for the first 60 seconds of conversation in any situation.

When Pete first e-mailed me, he immediately stood out. He related to me about his old days playing Counter-Strike, talked about how he loved my message of better human connections, and shared how inspired he was to write about the same subjects of bringing people together.

We jumped on a video call and two things were apparent: he genuinely wanted to know who I was and could hold engaging conversation almost effortlessly. I could tell that he was someone who had put himself out there in the past and gotten tons of real-world social experience.

He had recorded YouTube videos asking people all sorts of social experiment questions. He had spent years pushing himself to talk to strangers. And he even created a card game to help people get out there and start talking to new people.

Then I read his content. He was incredibly thorough and you could tell he was calling on his own experiences to provide legitimate advice. A lot of people “talk the talk” in social skills but few people have actually taken the journey themselves. For that, I have immense respect for Pete and the work he does. 

Welcome Pete…

There’s a person standing in front of you. Gazing into your eyes. Expecting you to say something.

You expect yourself to say something in reply, and your eyes grow a little wider as you start to realise that nothing’s coming.

Are you imagining it…or do you also see fear in their eyes? The silence has stretched too far to be comfortable and you’re desperate to break it.

You blurt out a sentence that’s barely relevant to what you were talking about. You even trip over the words as you say them.

“Did that make sense or did I make this more awkward than it already was?” — your internal dialogue.

The person responds. It’s a normal response. Thank God.

You’re out of danger for now, and your conversation has a starting ground.

If the above is your method for finding a starting ground, it’s not a very good one.

It works some of the time, sure. But it’s unreliable.

The starting ground of a conversation can be whatever you want it to be. You’re only struggling to find it because you haven’t decided where you want the conversation to go yet.

It’s like you’re driving a car with a steering wheel that won’t stop spinning around, and it’s not one of Google’s self-driving cars, either. It’s a regular old hand-driven sedan.

How do you honestly expect to reliably gain momentum in your conversations when you have no control over where you’re going?

I think it’s time you installed a new steering wheel, my friend.

How to steer the first 60 seconds of a conversation

Everyone you ever talk to will fit into one of the six groups below.

  1. Never talked with before. Sparks your interest.
  2. Never talked with before. Doesn’t spark your interest.
  3. Talked with before and dislike.
  4. Talked with before and feel neutral about.
  5. Talked with before and like. Not quite a friend.
  6. Friend.

What you say in the first 60 seconds of a conversation with a stranger will be different from what you say to a friend. The same goes for each combination of the groups above.

Categorising people into these groups helps you decide what you want to get out of each conversation.

In the rest of this article we’ll go over some examples for each group:

  1. What to open with
  2. What to follow up with in the first 60 seconds.

I suggest you come up with your own ideas for each group based on where you want each conversation to go.

Group 1: Never talked with before. Sparks your interest.

The purpose of this conversation could be to figure out whether or not you want to continue creating a connection with this person.

They’ve already got you interested…

Maybe they sound smart when they answer questions in class. Maybe they have a strange accent. Maybe they play the same sport as you. Maybe you just find them attractive.

So lead with what intrigued you in the first place.

Opener: Bring up the thing that sparked your interest and ask them about it


  • Hey I liked your answer to that question today. How’d you get so smart?
  • Hey I noticed your accent and wanted to say hi. Where’d you get it?
  • Hey I saw you at the gym. How often are you there?

If you just think your stranger is pretty hot and you don’t feel comfortable saying that outright, try something like this instead:

Hey, something made me want to talk to you. I’m not quite sure what it is… *cheeky, puzzled look on your face*. What’s your story?

Let’s say your opener and their response take up 20 seconds. Then what?

Follow-up Goal: Find out if their interest in the thing is similar to your interest in it.


  • What do you think about ___ (something related to the thing you opened with)?
  • What made you decide to get into ___ (thing)?
  • (Express your own view/idea related to the thing, then ask what they think)

I’m leaving these open-ended because they’re not meant to be followed like a script. What you say here depends on their response to your opener.

Those are just a few ideas for what you can say to figure out if this person is someone you want to continue investing in. They are by no means the only options.

Group 2: Never talked with before. Doesn’t spark your interest.

Unlike Group 1, you’re not overly interested in this person right off the bat, making it more difficult to come up with something to say.

To help that, you need to find something about them that interests you.

It’s more likely that they opened the conversation since you weren’t all that interested, so they’ll probably lead it. But if you get caught off guard and don’t know what to say, go for the hail mary.

Goal: Discover something about them that interests you.

You can preface it with something like “Hey I like asking new people this question.”


  • What’s something you’ve done that everyone should try at least once?
  • Do you remember what you wanted to be when you grew up?
  • What’s something your friends would say you’re great at?

Group 3: Talked with before and dislike.

You don’t really want to go around starting conversations with this person. If you’re talking to them it’s more likely that they started talking to you, so they’ll lead the conversation (like Group 2).

The difference is that you’ve already decided you don’t like this person.

You can either give this person a chance to redeem themselves, because maybe they aren’t so bad… or you can get out of there politely.

How many times do we think we dislike someone when really we just don’t know them that well? Maybe if we learned to have an engaging conversation with them they’d grow on us.

Goal A: Poke the thing you dislike (lightly) and give them a chance to show a different side of themselves.


  • If they seem cocky or aggressive: You seem like a pretty confident person. Have you always been confident?
  • If they seem like a know-it-all: You seem like a pretty smart person. Have you always considered yourself an intellectual?
  • So tell me what you like to do for fun when you’re not here?

And then if you still dislike them…

Goal B: Acknowledge them and give a reason to end the conversation.


  • Listen, it was good seeing you but I’m on my way to __.
  • Hey it’s good to see you, but I can’t talk right now. See you later!

The more assertively you do it, the less awkward it is. Don’t give them room to ask questions.

If it’s a networking event and you’re stuck talking with someone for longer than you wanted to you can say:

  • It’s been great chatting. I’m going to meet some more people. I’ll see you later.
  • I’m going to the bathroom. It was good chatting with you.
  • Or if it’s a group conversation you can simply walk away while someone else is talking and not addressing you.

Group 4: Talked with before and feel neutral about.

You don’t like this person enough to put any real effort into connecting with them, but you don’t dislike them enough to end the conversation. This is who you practise your small talk with.

Why not make the goal of the conversation to learn something new? They’ve probably done something surprising, significant, or clever in the past few weeks. Find out what it is.

Opener: Find something interesting they’ve done.


  • Hey, what’ve you been up to since the last time we talked?
  • Did you do anything cool on the weekend?
  • What’s up? Got any news for me?

Follow-up Goal: Learn something new.


  • That sounds cool. I’d love to hear that story.
  • Tell me about __ (thing they mentioned).
  • Have you heard anything interesting lately? In the news or anywhere?

Group 5: Talked with before and like. Not quite a friend.

Presumably you want to become friends with this person. You just don’t know them well enough yet.

You can become friends by spending time with them and sharing experiences. That’s the gist of it anyway.

Where Group 4 focused on learning from something in the past, Group 5 focuses on creating shared experiences in the future.

Opener: Get up to date with them.


  • How’ve you been?
  • What’s new?
  • Got any plans for the weekend?

Follow-up Goal: Plan a shared experience.


  • Let’s do something on the weekend.
  • Hey I’m doing __ with some friends on Wednesday night. Wanna join?
  • We should do __ (common interest) sometime.

If you’ve already planned something, invite them along.

If you don’t have their number yet, get it. You can tell them you’re going to organise drinks or something else with a few friends, and you’ll let them know.

Hot tip for making new friends: Be the one who organises shared experiences. Bar, sport, beach, restaurant, road trip, movie, whatever. If you always have something coming up you’ll have something to invite the people who aren’t quite your friends yet to.

Group 6: Friend.

You’re probably pretty comfortable talking with someone who’s in this group, so I don’t think I really need to tell you what to open with.

But here are some tips for making your friendship stronger.

Goal: Deepen your connection.

Remember the things they mentioned last time you talked, and check in with them:

  • Is your dog feeling better after eating that spider?
  • How was your girlfriend’s Mum’s birthday?
  • What did you end up deciding about that audio engineer job?

Give them sincere compliments.

Show a genuine interest in their lives and listen. Essentially, give a shit.

Don’t get stuck in polite conversation. There’s no “skin” invested in it. You’ve got to get at least a little bit naked (so to speak) in order to connect with someone.

Here’s how you do that comfortably:

We humans have just 4-8 basic emotions, depending on which study you read: joy, trust, fear, surprise, sadness, disgust, anger and anticipation. Everything we experience triggers a combination of these basic emotions. There aren’t that many combinations.

We may not have experienced the same activities, but we have experienced the same emotions. So when you look for common interests, you need to find something that sparks similar emotions​ in both of you.

Say Felipe is studying to be an architect, and Manuela is studying to be a doctor. Felipe doesn’t care about medicine and Manuela doesn’t care about architecture. They ask each other polite questions:

Felipe: Oh, I hear you have to study for a long time to be a doctor. How many years do you have left?

Manuela: Yeah, I’ve got another 2 years. 7 total. Although you never really stop learning. What do you want to design when you graduate?

Felipe: Bridges. I mainly want to design bridges. But I guess I’d be happy designing anything.

Manuela: Yeah I know what you mean, I just want to graduate already as well!

This is pretty boring, right? Neither of them are offering or asking for emotional information.

At this level of conversation they have to keep thinking of new topics every few seconds. The ideas will dry up pretty soon. This is why conversations often feel like hard work. It’s much easier to pause and explore one topic for a while.

So here’s what you do…

You don’t just listen to respond. You listen to understand them. You go deeper.

– Offer your own emotional information

– AND dig for their emotional information.

Keep digging until you understand their way of thinking. Until you feel the emotion they’re talking about. Then show them that you understand by sharing a similar experience of your own.

These questions are your friends:

– WHAT do you like about that?

– WHAT made you want that?

– WHAT scares you about that?

– Essentially any question that uncovers “What makes you feel that way?” or “What makes you think that way?”

WHAT tends to work better than WHY because WHAT feels like you’re curious and WHY can sometimes feel like an attack.

“WHY do you like that?”

“Because I do. What’s your problem?!”

So back to Felipe and Manuela. Now that they know how to “listen to understand”, how does their conversation go?

Felipe: I mainly want to design bridges. But I guess I’d be happy designing anything.

Manuela: What do you like about designing bridges specifically?

Felipe: Well I haven’t actually designed one yet, but for some reason I keep picturing myself standing on top of a huge bridge that I designed. I don’t know. It just makes me feel alive.

Manuela: Yeah that sounds pretty cool. What do you mean by ‘alive’ though?

Felipe: Hmm, well the bridge started as an idea in my head, and now I’m standing on it. It’s like having control over everything, because I created it.

Manuela: Oh I know that feeling! That’s how I feel when I think of saving someone’s life at the last minute in the emergency room. Boom… Doctor Incontrol.

Felipe: Haha. Is that what made you decide to become a doctor? Because you like feeling in control?

Manuela: Yeah, I guess it is.

Felipe: Wow. That’s the same reason I decided to be an architect. So does that mean you hate it when other people boss you around too?

Manuela: OMG that’s the worst!! I can’t stand it when other people tell me what to do.

Fun! Turns out they’re both control freaks. THAT’s their common interest. Now they can geek out on that instead of churning through countless emotionless topics that they don’t connect on.

That bit about Felipe and Manuela was taken from my guide: Make Real Friends: 3 Conversation Hacks You Never Knew. You can get it at that link. It’s a free 10-minute rollercoaster ride that teaches you how to connect with other humans on a deeper level. I’ll tell you what to say, how to say it, and why it makes a difference.

Final words – Using this guide effectively

If you’re reading this, you’re probably the kind of person who spends a lot of time thinking. You live your life in analytical mode: absorbing information and marinating it inside your think tank.

You get a kick out of understanding things deeply and like to plan stuff out before you do it. And that’s great. I’m one of those people too. That’s why I gave you a roadmap as a starting point.

But starting a conversation is a creative problem, not an analytical one. You’re not going to analyse your way into feeling comfortable.

… So how do you solve this creative problem?

By doing.

By not overthinking.

If you’re going to start a conversation with someone, you have to accept that you don’t know how they’ll respond.

And this is a good thing. It’s what makes conversation fun.

Imagine how boring it would be if you knew exactly what the other person would say?

The best way to get better at starting conversations is to go out, start conversations, and push through the first 60 seconds.

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