Hey, I’m Ian from charismahacks.com, and I help ambitious men and women transform their personal and professional relationships by becoming more charismatic and learning how to connect with people on a deeper level.
Learning how to start exciting and memorable conversations with anyone is one of the biggest things that has helped me change careers successfully multiple times, take my dating life from zero to selective, and make awesome friends that help me grow in every way.
The truth is that starting engaging conversations is one of the most important skills that you can have, whether you’re looking to connect with VIPs in your industry or meet your dream guy or girl, it all starts with a conversation.
In this guide, you will learn:
- 3 ways you can start an engaging conversation with anyone, anywhere (bars, networking events, the gym, etc.)
- The 2 most important tips to authentically connecting with the other person and being unforgettable
- My bulletproof strategy for never running out of things to say (and controlling the direction of the conversation)
- The most important hack for starting conversations and transforming your social life
- How to radically change your habits to transform your social life in the deepest and most efficient way
You will also, most importantly, learn how to become a person that starts fun and exciting conversations wherever you go with a practical, action-oriented 5-day challenge at the end of the guide. You didn’t think you were going to be able to read all of this and not take action, did you? 🙂
It’s very important to read this in chronological order. The guide is designed to be systematic and comprehensive, so if you skip a part, you might find that the other sections build off of it. Just reading the later sections won’t be as effective unless you read the whole way through.
My goal is for this guide to be the most comprehensive guide on the Internet for starting a conversation with anybody, so if you have any comments or questions, feel free to email me at firstname.lastname@example.org for any questions!
Table of Contents
- Intro: Why Starting A Conversation Is The Easiest (And Hardest) Thing In The World
- Bulletproof Psychology and Mindset
- What Makes Someone Want To Talk To You Without Running Away
- How To Start A Conversation With Anyone, Anywhere
- How To Never Have An Awkward Silence Again
- How To Joke Around And Be Playful With People You Just Met
- How To Connect On A Deeper Level With The Other Person
- FAQ’s (How To Enter Into Group Conversations? What If We Have Nothing In Common? How do I connect with a VIP?)
- Five Day Challenge
Intro: Why Starting A Conversation Is The Easiest (And Hardest) Thing In The World
Starting conversations. For some reason, it comes so naturally to some people. My friend Matt can start a conversation with just about anyone. He says something goofy or asks a funny question, and boom – the conversation is off to the races!
We inherently know that people make snap judgments. I think that’s why so many people are initially hesitant to even start conversations – it’s almost as if you mess up, you’ll never get a second chance to make an impression on that person!
We also tend to judge ourselves harshly by other people’s first impressions of us. I worked a door-to-door sales job one summer. In one day I hit 120 houses, twice. How many sales did I make?
It was devastating to my self-esteem. Every interaction, every time someone told me to get off their property, and every time someone shut their door in my face, I died a little inside. I took it so personally – it felt like the person hated me (which they did).
I quit the next day.
This was (please don’t kill me for saying this) remarkably similar to my experience talking to girls on the streets. In the course of a few months, I talked to hundreds of girls. If a girl was pretty, I would walk up to her and say something like “Hey, this is random, but you are super pretty and I’d be kicking myself the rest of the day if I didn’t talk to you.”
The thing is, and it might be sad to say, talking to all of those girls was really only about me getting over the fear of rejection. And it worked. Kind of.
I became scared not to talk to girls. I would judge myself if I didn’t have a conversation with a girl on the street that day. Twisted, right?
The biggest takeaway from all of this? There are two.
Starting a conversation is remarkably easy.
You can start a conversation by saying something like “hey can you pass me the fork?”
The real hard part is our fear of judgment.
We want to be liked. We want the interaction to go well without too many awkward silences, or too many moments where we have no idea what to say. More than anything, and it’s a cliché, we want to feel like we are being ourselves.
Understanding what’s holding us back to starting conversations with anyone, anywhere is extremely important. Which brings us to our first section…
First Things First: Psychology
Most people that give advice about how to start a conversation will tell you two or three tips about what to say, but skip over the most important part – your mindset.
So what do I mean by your mindset anyway? You might say “I’m here, I’m reading this, doesn’t that mean I’m working on my mindset?”
Yes and no. By mindset, I mean the cluster of beliefs that you have that go to the core of who you think you are, why you do what you do, and inform what you want. Pretty deep stuff, huh?
The important thing to recognize is that most people aren’t conscious at all of these beliefs, but they run their lives. I, for example, used to believe that if I started a conversation with someone in a café or a bar that I would annoy them. I believed that they clearly wouldn’t want to talk to me, and that the least annoying thing I could do is keep silent.
If they wanted to talk to me, they’d start a conversation with me, right? Does this sound familiar to anyone?
This, however, is just the tip of the iceberg. In fact, it probably goes as deep into our own belief in our self-worth, lovable-ness, and all the tender, vulnerable, and profound scary parts of ourselves that we usually steer clear from.
I will say that in my own case, the thought that other people wouldn’t want to talk to me was directly related to my own low self-esteem. I didn’t think that people would think that I have anything interesting to offer. They wouldn’t think that I have anything of value.
This didn’t just manifest as not starting conversations with people. I was generally afraid of intimacy; afraid to get to know people, afraid to open up, afraid to share my opinions. My voice would shake when talking to other people for the first time, or people that I respected or was intimidated by. I would talk quickly, stammer over words, and feel uncomfortable looking people in the eye.
And I wouldn’t start conversations with people. Part of the reason was to avoid the drama “what will they think of me?” or “will they like me?” Unfortunately, at the time, I was totally blind to how deep this really went. It was just who I was. Or who I thought I was.
This isn’t to share my sob story to you.
What we believe conditions how we think, feel, and move in the world. Our beliefs manifest themselves in every activity we do, from starting conversations with strangers to how we eat breakfast.
This is why it’s incredibly important to start with beliefs. Using a couple of tips without working with and being aware of your own psychology is like eating candy for dinner: it’s good for a little bit, but has no lasting nutritional value.
So how do we start?
Maybe you wan to run off to psychotherapy right away (probably not necessary). I have another recommendation.
Be aware of yourself when you are needy.
Nick Notas, a dating and confidence coach (for men), wrote an amazing piece called “How to Liberate Yourself From Low Self-Esteem” which you should definitely check out. Nick talks about being openly vulnerable and developing a “mindset of choice” to transform low self-esteem and neediness.
I LOVED one example, and want to share it with you here:
“You want to build an interesting lifestyle and make friends.
Wrong path: You don’t go to local events or meet-ups because you might not “fit in”. You’re worried about being judged. You get lonely and think about how you don’t have many friends. You convince yourself that there must be something wrong with you. You continue the cycle of staying in because no one will want you around.
Right path: You go out because you want to try something fun and challenging. You remind yourself to relax and that you don’t have anything to prove. Instead, you focus on getting to know people that interest you. This puts you in a mindset of choice and abundance. You now look forward to going out because you can be yourself around people that actually matter.”
Simple, right? But not easy. You see, neediness is one of the most common and unattractive cues that other people pick up on that makes them not want to hang out with you.
The funny thing is that no one can ever put their finger on how they know someone is needy. Maybe it was the three unanswered phone calls. Maybe it was talking too quickly. The point is that neediness is conveyed and picked up at the gut level, and everyone can sense it.
So what to do about it? Develop the habit of realizing when you are being needy.
It might sound tricky, but it really isn’t. Another way of saying this is to see if you are doing something solely to impress another person. Are you doing something to be liked, or are you doing it out of a deeper sense of value that the activity gives you?
You can even do this right now. Just take a second to stop and reflect, “When was the last time I hung out with someone to not feel lonely?” or, “How do I use people to feel good about myself?”
The wording for each one might differ, and it’s good to try and play with this. The point is to see how you might be using other people – for love, sex, to feel good about yourself, to not be lonely, etc. Eventually, you want to stop engaging in interactions based on neediness.
This isn’t a simple process, and can take months, even years to fully be honest with yourself.
You might be thinking to yourself “I thought I was reading this to learn how to start conversations!” Don’t worry. You are. And this is the deep, transformative work that reward you in unimaginable ways years and years down the line.
It isn’t sexy – that’s why you won’t ever really hear people talk about it.
Next up in psychology: Transforming Subconscious Beliefs
Leapfrogging off of neediness, you will want to see the different stories that you tell yourself when talking with other people.
Remember when I said that I didn’t think that people would want to talk with me? That’s an unconscious beliefs. I had no idea if that thought was true or not, but it was what I believed.
Have you ever thought:
- What if the other person doesn’t think I’m interesting?
- She’s with her friends, she probably doesn’t want to talk to anyone else
- What if we start talking and it’s awkward
Any and all of these things has prevented just about everyone from starting a conversation with someone that they wanted to talk to.
So how do we transform these unconscious beliefs?
The first step to doing any of this is recognizing the story that we’re telling ourselves and calling ourselves out.
Say for example you want to talk to a girl in a bar. She’s laughing with her friends on the other side of the room and you think, “there’s no way that she wants to talk to me.”
The three steps to transforming an unconscious beliefs are: In that moment, first recognize the story that you are telling yourself. Call yourself out. Then, question if it’s true or not. How do you know? And finally substitute your narrative with another one.
What are some examples of this?
- When you catch yourself thinking “she is talking with her friends, she doesn’t want to talk with anyone”, realize “of course she probably wants to have a fun and exciting conversation with someone new, that’s why people go to bars”
- If you want to say something but hold back because you think it’s going to sound stupid, catch yourself and realize “Man, I’m taking myself too seriously”
- You show up at a networking event and don’t know anyone so you take out your phone. Stop, take a deep breath, and realize “I have value to give people here, and it would be selfish of me to withhold that from people”
Think about it. If someone awesome came up to you and started having an engaging conversation, would you be open to it? Of course! So why wouldn’t anyone else?
The truth is that if you were to do these to things right now (being aware of when you are acting from neediness, and transforming your unconscious beliefs), 80% of the work would be well under way. Obviously it’s important to reinforce the transformation with tangible results, but the real crux of this works starts from the inside.
It’s an inside-out game, not the other way around.
Finally, it’s incredibly important to talk about…
Yes, expectations. If you catch yourself wanting the conversation to go a certain way – say for example, trying to get the other person to like you – you’re undercutting yourself from the start.
Expectations are a manifestation of neediness. They make conversations into subtle transactions that stops them from ever becoming truly authentic. Or worse, they stop you from even talking to people in the first place.
Experiment with this: “what would it be like to start a conversation with no expectations?” You wouldn’t be trying to make the person your friend, and you wouldn’t be trying to make them like you. You would just be being yourself, comfortably (which is a very attractive trait).
Now that we’ve covered the mindset aspect…
What Makes Someone Want To Talk To You (Without Wanting To Run Away?)
Still under the banner of psychology (we’ll get into techniques and tactics soon, I promise) comes the question, “Now, why would anyone want to talk to me?”
Again, possibly controversial, but I want to point out the number one reason someone would want to meet or get to know someone else, whether at a bar, networking event, or the gym.
Now, Value is a vague, ambiguous term that means different things to different people in different context. To some people, “Value” might be conveyed through a material means – the car they drive, the watch on their wrist, etc.
To other people, it could be how much indie rock music you listen to and if you read cool books. Again, different things to different people.
Before delving in to this too much, I would like to make a distinction between External Value and Internal Value.
External Value is what we just mentioned. It is the accessories around your life, and I don’t mean just flaunting wealth. External Value includes not only your car, watch, etc. It is your clothes, your books, the music you listen to, maybe best described as what you consume. Shopping at Whole Foods relates to your External Value.
Internal Value is a little more fun to talk about. Your Internal Value is largely predicated on your mindset, which we’ve discussed at length. What I’ll talk about here instead is how Internal Value is conveyed.
Obviously, as we’ve discussed, it really helps to focus on your mindset. But more externally, your sense of Internal Value is conveyed in everything you do. I mean your body language, your interactions, the tone of your voice, if you laugh, how much you laugh, etc. The important thing to recognize is that there are too many variables here to consciously control.
Yes, some people recommend taking up power postures or maintaining open body language. Don’t get me wrong, this of course helps. Having open body language and not talking quickly will obviously make someone more open to want to talk to you. But more powerful than simply consciously shifting your body language is your state, which is highly determined by your Internal Value.
Think about it, if you knew you are totally confident that you are funny and can make anyone laugh, or if you know that you can provide value that will help someone else, how do you act when you are around that person? Are you frantic, and worried what they think of you? Maybe a little. But chances are you are calm, collected, and not too worried.
The reason that I mention all of this is location.
Now, in many places, starting a conversation is easy. If you’re at a coffee shop, there probably aren’t too many people trying to talk to each other at the same time. It’s easy. All you have to say is “can you pass the fork?” or something of the kind, and you’re in.
In closed spaces designed for people to talk to each other – bars, networking events, parties, etc., however, if you want to talk to people, you are competing for airtime.
What does all of this mean?
In places where people are competing for airtime, it’s important to be a person of value. Again, this doesn’t mean that you have to have the sexiest shirt or fanciest watch.
You could have Value by being incredibly down to earth. You can tell funny stories. If you connect with someone on a deep level, that’s incredibly valuable. Even just being relaxed and present while listening to someone is really important.
Also, you know, if you’re handsome or beautiful, it doesn’t hurt.
If someone has low Internal Value, this might manifest as them looking around a lot to see who else they can talk to if they are in a conversation with somebody. It might mean having closed body language. It most definitely means not starting a conversation with anyone.
Okay, are you ready to finally get on with the rest of the guide and learn the actionable things you can do to start conversations with anybody?
I thought so.
How To Start A Conversation With Anyone, Anywhere
Have you ever been stuck somewhere, maybe an airport, maybe on a bus, and you see someone awesome that you really want to talk to? Maybe it’s a beautiful girl, maybe he has a sweet tattoo.
Whatever it is about this person, you just want to meet them. You could be at a party and someone that you’ve met but always wanted to get to know better is off on the other side of the room talking to her friend. Suddenly, you jump forward two hours and you’re leaving the party and think “Man, if only I’d talked to her…”
If only. We’ve all been there. You thought that you’d seem weird, or maybe you didn’t know what to say or how to start the conversation. Maybe there was a group conversation and you didn’t want to interrupt.
The good thing is you are here, reading this. But where to start? Don’t worry. I’m not going to leave you hanging.
- Understand your setting
Bars aren’t networking events. Networking events aren’t gyms. The gym isn’t a café. And the café isn’t work. Savvy?
What are people there to do?
People, when they go places, do things associated with those places. Maybe they work at work. They are with their friends at bars. They workout at gyms.
Obvious, so why does that concern us?
Let’s take a look at this picture for a second (excuse the rudimentary, caveman drawings J). A normal person in a gym will be working out. That’s what they’re there to do. Strange people and one’s that we usually avoid conversations with have a different agenda.
As you can see in the “Weirdo” section, the “activity” of the two people is different. One wants to work out, while the other seems to just want to talk to people. But what happens in the third, with what I call “Organic Conversation”?
In the organic conversation, the people are there for the same reason: both are working out. The difference is that if you are in a place for an authentic reason, doing something that you want to do, it’s much easier, and much less weird to start a conversation.
You see, people get weirded out when it seems like all you’re trying to do is meet other people. Unless you’re at a meetup event, people don’t go to the gym for icebreakers.
Real life isn’t summer camp.
Truthfully, you will want to have your own thing going on. If you’re at the gym, you better be damn sure that you’re going for the right reasons because it’s pretty weird talking to someone who just looks like they came to meet people.
Same goes for work. Even the same thing for networking events, where the goal is to meet other people. If you aren’t in the place for an authentic reason, it will be fishy to the other people.
The point is to understand the context. In order for conversations to not be awkward or for people to think that you’re totally weird, understand the environment and what the other person is doing in the environment.
We talked about this when it comes to neediness. Every situation and person is unique, and all I can really say is to check in with yourself and see if you are coming from a place of neediness.
- How do I want this person to feel?
Now that you have a rough understanding of where you are, you’re not needy, you’re doing your own thing. And you’re about ready to start a conversation.
Well, let me just say, hold the f&#*ing phone.
A quick, very effective hack that you can implement that will improve your conversations is to pause either right before you start a conversation or right before you enter the event.
Before you enter the conversation, ask yourself “How do I want this person to feel while they are with me?” Trusting? Happy? Excited? Finding the exact emotion will give you a reference point that you can keep coming back to if you find yourself lost or nervous.
Another way you can rephrase this is “how do I want to feel?” Right before entering a room, or right before starting a conversation with somebody, if you want to feel happy and exciting, imagine you just won the lottery. Or think of something that would make you happy.
If you visualize this for even five seconds, your brain won’t be able to tell the difference, and when you enter the room or conversation, people will respond to your energy.
For the next three pieces of advice, I’ve been heavily influenced by Charlie Houpert from Charisma on Command. I highly recommend watching this youtube video of his where he quickly and easily breaks down three techniques on starting conversations with people. Though he uses different terms like “Human Twitter” or “Human Google” (gotta love that), I preferred using siri as I ask more questions to siri vocally 🙂
- Specific Observational Comments
Before I jump into this, I want to say the most important thing you can do when starting a conversation is to remove your internal filter. You know that censor in your head that says “you better not say that”? A lot of times, that censor is right. You don’t want to say something screwed up or upset and offend a ton of people.
More often than not, though, I find that people censor themselves too much. Whether if we are worried what people will think about us or you just think to yourself “this is so weird”, chances are you are overreacting.
So turn off your internal filter!
So the key to making a specific observational comment to someone, whether you are in a bar, the gym, wherever, is just to give voice to your internal dialogue.
Maybe someone is studying right next to you.
You might be able to say, “Wow, that looks really hard. What are you studying?”
Another example would be, “Ah, Biology, it was a very happy day when I finished that class.”
The key is just to say whatever comes to your mind. A lot of advice that people give on starting conversations tells you to give people compliments. Compliments are great, but if they aren’t authentic, people can smell them from a mile away and can tell if they are contrived.
Instead of forcing yourself to give a compliment to someone, all you have to do is give voice to whatever you’re thinking (unless what you’re thinking is inappropriate).
Now, you may ask “yes, but how does this keep the conversation going?” Don’t worry. We have a section for that. For now, the only thing we are focusing on is starting the conversation, and making a specific observational comment is a great start.
- Situational questions
Questions are also fantastic vehicles for starting conversations.
Remember I was talking about my friend Matt? Matt asks crazy questions. We will be in the check out line at a grocery store, and Matt will ask the cashier, “So what’s the best part about being a cashier?” One time we were at a party and he asked someone “Do you believe in ghosts?”
Matt goes big with his questions. Also, he doesn’t give a damn. The interesting thing is that I get to see him ask tons of different, weird, and awesome questions to tons of different people (and see which ones go well or horribly wrong).
Over the years of seeing him either make someone’s night or crash and burn, I’ve gotten to see what some of the ingredients are to starting great conversations by asking questions.
Again, like most of what I will tell you in this guide, the most important thing is to be sincere. Just like giving people contrived compliments comes off as slimy and try-hard, asking inauthentic questions for the sake of starting a conversation is very noticeable.
In a bit of very Dale Carnegie-ish advice, I’m just going to say that it helps to be interested in the other person.
Also like the observational comment portion, try to uncensor yourself.
Two ways to ask a question are:
- Asking for a recommendation. This is a great way to start a conversation. Whether you are at a café, bar, or just need some help at the gym, asking for a recommendation.
- Pretend the other person is siri. You know on iPhones (not sure about other smart phones), how you can ask siri questions and the robotic woman’s voice will answer no matter how ridiculous? Try to think of the other person as siri. This works best in situations where you might have a question about the location, what they’re doing, what it’s like, etc.
As always, be cognizant of coming off as needy, and be careful about having expectations going into the conversation. If you want it to go a certain way, or you have an agenda (“I want to get her phone number”, or “I want this person to like me”), the conversation probably won’t go as naturally and smoothly as you want it to.
Finally, we have:
- The Cold Intro
Now, I know this sounds difficult. People usually think that people would react weirdly to just come out of nowhere and introduce yourself to someone else for the first time, but surprisingly the opposite is true.
Taking the location into consideration is very important with introducing yourself to someone randomly. If you are at a bar, a networking event, or any place that is designed for you to meet new people, a cold introduction can be the easiest thing in the world.
It’s worth repeating that it would probably be weird to introduce yourself to someone at a café without making a comment or asking a question first. But at a bar (depending on how you feel), a networking event, or a party, a cold intro can work wonders.
Here are some example scripts:
- “Hey I’m Ian, I don’t think we’ve met”
- “Hey, I’m Ian. So who do you know around here?”
- “Hi, I’m Ian. What’s your name?”
These might seem trivially simple, but the real key to pulling them off isn’t in the words. It’s in how you say it. You can play with this. Talking slowly, smiling, and feeling comfortable in your own skin make people much more likely to be warm and respond openly.
After You Start, How Do You Keep It Going?
So you have a conversation going! Congratulations. Now you might be wondering “how do I not crash and burn and take this conversation to its fiery grave?” Don’t worry. I got you covered.
Because this is a guide on starting conversations, I’m not going to go into as much depth as I could about keeping conversations going, though it’s important. Teaching you how to start conversations without helping you with the actual conversations themselves is a little bit like giving you keys to a car knowing full well that you can’t drive perfectly.
Also, feeling comfortable and fluid in a normal conversation with anyone goes a long way to making you making you more confident to start conversations with people in the first place.
I’m going to start with seemingly obvious things, and then get more technical.
- Listen, listen, listen
Look, your mom was right. Listening to people makes them feel special. And I don’t mean nodding 20 times without stopping, and I don’t mean being quiet but thinking about your next trip to Thailand.
Active listening is surprisingly hard, but is absolutely essential for connecting with people (and getting them to trust you).
So what do I mean by active listening, and how does it differ from normal listening?
Have you ever been telling someone about something, and then that person hijacked the conversation and started talking about themselves? Does that person do this a lot? That person may be what I call a conversation hijacker.
Don’t be a conversation hijacker. It’s selfish. It’s ugly. And people won’t like you.
Instead, an active listener is present with the other person while they are listening to them. An active listener will ask questions and for clarifications related to what the other person is sharing. An active listener cares about the stuff other people share with them.
When it comes to listening, that’s basically it. Being interested in the other person and caring about what they have to say help people open up to you in ways you could never have imagined.
And laugh. This is self-explanatory. Again, if you are warm, people are much more likely to feel comfortable with you and open up.
- Have your elevator pitch
Now we get a bit more technical. You know elevator pitches? You walk into the elevator, a senior VP happens to be stuck with you for 30 seconds, and you want to sell and convince him on that amazing idea you had for a dog-walking app?
This is exactly like that.
Except… don’t sell anything to people.
The elevator pitch is another way of addressing the reality that people are going to want to put you in a box as soon as you start a conversation with them. So what does this look like when meeting people for the first time?
Think about the most common questions people ask:
“Where are you from?/Where do you live?”
“What do you do?”
And maybe the contextual:
“So, how do you know Jerry?”
“How do you know about X,Y,Z?”
I can’t emphasize this enough: Prepare for these answers!
You know people are going to ask you these questions every single time you meet someone new. And how often have you thought about making them interesting, or actually sharing something deep about yourself? If you were like me, probably never. But these questions provide amazing opportunities for your “elevator pitch”.
Now, I know in this metaphor it might seem sleazy to be “selling yourself”, but remember, people are judging you anyway. You’re going in some box, and taking control of these questions gives you a little more flexibility when making a first impression.
So think, right now, what do you do? How would you explain it to someone to make it sound exciting? How might you use this opportunity to connect with the other person?
Instead of keeping this at the surface level:
“I’m in sales and blah blah blah”
Let’s bring it deeper. Share what is important to you.
“I’m in sales for a X company and it’s really rewarding selling people products that change their life”
Or make it funny
“I’ve sold out: I’m in sales but that’s just to put food on the table while I try to make it big with my KISS cover band.”
With every one of these questions, you want to be doing one of three things: introducing emotion, sharing your values, or making it funny.
Thoughtful responses to the everyday questions that you get will make you much more memorable and is a great way for someone else to relate to you. For example if you say that you are a manager, the person may just nod their head and say “cool.”
But if you also mention that you love working with and mentoring people, and that it’s really rewarding to see someone grow, it’s a whole new ballgame. That person might be a teacher and totally relate. Or they might be a parent and understand you from a different perspective. The point is that you now have much more to connect over than simply the fact that you are a manager.
So think about this. What are the common questions that people ask you, and how can you share a deeper part of yourself, or make them funny so that people will remember you?
- Never run out of things to say again
So you’re talking. Things are going well. You mentioned where you’re from. Maybe you just talked for five minutes about skiing.
And suddenly, you see it: all obvious conversation topics are coming to an end. The light at the end of the tunnel is getting closer.
How do you keep a conversation going when you run out of things to say?
Welcome to the very newest episode of Choose Your Own Conversational Adventure!
Don’t you love stock photos?
You know those “Choose Your Own Adventure” books (that usually left me being trapped in some cave forever)? Maybe you haven’t. In these books, everyone starts at the beginning on the same first few pages, but then you can make a series of decisions and the book tells you to skip to different parts.
The books were usually mystery books, and you might have been trying to solve riddles or something.
The funny thing? Every conversation is a choose your own adventure book (or conversation… whatever). Once a conversation starts, you can (within reason) take it just about anywhere. Some directions may feel more natural than others, but nothing is stopping you from talking about kittens, or the meaning of life.
But how do you make the conversation naturally flow, while choosing your own adventure?
Easy. Just use the word association technique.
Word Association Technique
Say someone was just talking about cats. Quick, what do you think of when you think about cats? Any stories come up? What do you think about cats? Any opinions? I’m sure you could think of 2-3 things right now.
Now, if you feel the conversation coming to a lull, all you have to do is use the word association technique. As a bonus, to make the conversation even more interesting, you can try to weave different conversational themes while jumping off from the theme that the other person was just talking about.
Confused? Here are a few examples:
“So, it’s been nice out recently…”
“Yeah, you know, I just came back from Spain and it was incredibly hot. It’s kind of a relief to be back here.”
What just happened? I took weather and made it into a conversation about Spain. Boom. I just chose my own conversational adventure.
“The warriors have been pretty good recently…”
“Yeah so they say. I haven’t actually watched many games but I get up early every Saturday to watch soccer. I think Steph Curry actually said that he loves soccer too.”
These might sound contrived while you’re reading them, but by using the word association technique, while also using those words as a springboard to share something interesting or deep about yourself, you can keep a conversation that looks like it is going to die going quite naturally.
Keep It Lighthearted
Don’t copy serious Ian.
This is something that a lot of people don’t talk about because it’s kind of hard to explain. No one wants to hang out with a boring person, or someone that’s too serious.
People crave play. Think back to the last time you messed around with someone. Was it one day ago? One week ago? Months? We’re generally so afraid to step out of line, that we take ourselves too seriously. One of the best ways to break the ice with people? Joke around with them.
Again, this is a guide to starting conversations, so I won’t go as deeply as I could into this, but here are a few easy tried and true ways to joke around with people.
- Inside Jokes
Sometimes referred to as “callback humor”. This might take some practice, but it is the easiest way to joke around and connect with the girl we’re with.
The idea is to reference something that you have previously talked about, either in another conversation or earlier in your conversation, in a joking way.
For example, say you were talking about how a tiger escaped from the zoo at some point earlier in the conversation. You leave the restaurant, turn the corner, and you jog ahead to look around the corner making sure it’s safe for her.
“No, there aren’t any tigers around here. It’s safe to go this way,” you say with a smile.
Or maybe she was just telling you how she likes to listen to music and sing in the shower.
Later in the conversation, she asks you what you’re up to the next few days, and you say something like “I don’t know, but I’m definitely going to try annoying my neighbors by singing in the shower and see how it goes.”
When you reference an earlier part of the conversation it not only makes her laugh, but it also creates a little inside joke between the two of you. Have you ever had any friends who you had inside jokes with? It was like only the two of you know what is going on, right? That’s what this does.
Last note: inside jokes are all about the timing. Try remembering a few things that you talked about earlier in the conversation and wait for the right moment to use callback humor.
- Tell Hilarious Stories
This could be a guide onto itself, but I’ll quickly explain one of the easiest and most effective hacks for telling a great story.
Act out Characters
So easy, yet so effective.
So what does this look like? When you’re telling your story, and you want to either voice out what someone says or thinks, pause. Make a facial expression that really exaggerates what the person looks like or felt like, and in your best “bad” impersonation (usually the less realistic, the better) of that person’s tone of voice and how they talk.
Impersonations are funny in and of themselves. Many comedians don’t even say jokes, they just do impersonations. In fact, you don’t even have to say anything objectively funny. Just by slowing down and acting out a character in the middle of your story can give it a hilarious context.
(What acting out a character might look like…)
Deepening The Conversation
You’ve been talking. You know a little bit about each other. Maybe you’ve even joked around with the other person. But how do you make the conversation really memorable?
Did you get past the small talk to actually get to know the person? Will you ever hang out with them again? Go on a date with them?
I’m not saying that small talk isn’t important. In fact, it’s how most people relate most of the time and is an important social dance. It lets people know that you’re not crazy. The problem with it though is that, whether you’re at a party or on a date, a lot of people have a better time connecting with deeper conversation.
A lot of advice on connecting on a deeper level with people pretty lousy. People say ambiguous things like “listen more” or “ask hypothetical open-ended questions”. Great. But how am I supposed to ask someone I’ve never met before “where is your dream place to travel?” or “what is your spirit animal?” off the bat without coming off as weird?
The good thing is you don’t have to, and instead you can use these three techniques to authentically connect with anyone on a deeper level without coming off as a weirdo.
- Conversational Hooks
So you’re in the office lounge and someone comes in and asks “How’s your day going?” or you meet someone for the first time and they ask, “What do you do?”
How do you respond? “I’m fine. You?” or “I’m in sales right now but I’m looking to transition to…” Feels like a meaningless conversation, right?
People desperately want to connect with each other, especially if the other person is an introvert.
Let’s imagine that you just met someone. You’re going through the small talk dance, and then you leave a “hook” – something that recently happened to you that shows a deeper side of you. It can either be something you care about, or your values – anything that shows a little more of who you really are. No, don’t talk about your divorce, but maybe what you did this last weekend and how you felt is a good start.
Pete Zbrojkiewicz from Beard Strokings, a site where he helps people have more engaging conversations, calls this “Getting Naked” in conversation. In his guide “3 Conversation Hacks You Never Knew”, he mentions offer your own emotional information AND dig for their emotional information”.
You might be asking yourself “so, how do I even get to the point of sharing my own emotional information?”
Let’s look at examples:
“Hey how are you?”
“I’m great. I got to catch up on a lot of reading this last weekend which I’ve been meaning to do for awhile.”
“So, what do you do?”
“I work in sales at a big company, but that really just puts food on the table so I can play with my band on the weekends.”
See the difference? It’s important not to drone on about your personal life or weekend. If the person is interested or just nice, they’ll ask you about the hook that you put out without even realizing it. It’s also important to realize that if they don’t “bite”, it’s okay. It doesn’t mean that you have a bad hook, just try three times before trying a different one, or rewording the hook you’ve been using.
- Embarrassing Secret
By revealing a small, embarrassing secret, you share something embarrassing about yourself to whomever you are with. What this does is create a secret between you and that person, and it lets that person trust you a little bit more.
For example, if you are at a networking event and just starting to talk to someone new, you might say, “This is kind of embarrassing, but this is my first time here and don’t know anyone here. Have you been here before?” Or, “I think I bombed that test last Friday. How did it go for you?”
If you share something honest that is a little embarrassing it can endear you to another person very easily.
- Memorable Questions
Remember I just mentioned Pete from Beard Strokings? This is the part where he mentions “digging for their emotional information.”
We’ve talked about starting a conversation with a question, as well as listening, and just being generally interested in the other person. How, then, do you ask a memorable question?
Most amazing questions are authentic, specific, and unique. So how you do this? We’ve gone in depth about how it’s important for the question to be authentic. No one wants to ask (or answer) a throwaway question.
Pete recommends asking “What” questions instead of “Why” questions, because “Why” questions (e.g. Why do you like running?) are too aggressive and open-ended. A better question might be “What do you like about running?”
Specific, probing questions help demonstrate authenticity. You don’t have to ask huge open-ended questions. Conversations start deepening when you have a specific question that arises out of authentic curiosity. Think about what the other person’s day is like? What do they actually do all day? What are parts that no one knows except people that actually do it?
To a barista “So, I’ve always wanted to know, how much coffee do baristas actually drink?”
To a person that lives in an interesting neighborhood “So what’s it like to actually live in San Francisco? I’ve always been curious.”
To a taxi driver “Who was the weirdest person that you had to drive today?”
With specific and interesting questions, people are usually happy to open up about themselves.
Frequent Questions and Specific Problems
“Okay,” you might be thinking to yourself, “now I have all of this information, but it’s just theory. How do I actually use this stuff in real life?”
If you weren’t asking yourself that, now is a good time to start. All of this is pretty useless if you can’t apply it to real interactions with real people and get real results.
Now that we’ve covered the psychology, we’ve gone into how to start and continue conversations, and we’ve even discussed different ways to deepen the conversation, or take it in a different direction, I’m sure there are still questions bugging you like:
“What if we start talking and there is an awkward silence?”
“How can I enter a group conversation without seeming weird or needy?”
“What if we don’t have anything in common?”
All valid questions. A lot of the advice that I’m going to be giving will be a rehashing or a reframing of stuff we’ve already talked about, but it will be helpful to see how this plays out in actual situations that people struggle with.
“How do I have less awkward silences?”
Ah, awkward silences. They remind me of early high school – except they also happened in college and after college in abundance. Still, feels like high school, no?
First, let’s break down awkward silences into two categories:
- Awkward silences with people that you don’t want to have awkward silences with
Think a guy/girl that you meet for the first time and are attracted to, someone at a bar or networking event that you wanted to meet, etc.
- Awkward silences around people that you’re fine having an awkward silence with
Think someone you aren’t particularly trying to impress, or even just a good friend. The thing about group 2? If you really don’t care about a conversation going silent (say like having dinner with a good friend or significant other and you don’t even need to talk), then it’s really not awkward. For you at least.
So we are going to steer clear of group two for now and focus on group one “Awkward silences with people that you don’t want to have awkward silences with”.
What does this already remind you of?
Go get yourself a cookie if you thought “neediness”. Yes, when you want the conversation to go well, or you are expecting a desired outcome, then you will inherently abhor awkward silences, avoid them like the plague, and treat them like a vacuum that you need to fill with anything and everything that comes to mind.
Let me reframe this for you.
Being comfortable with silence is actually an indicator of high Value. It shows that you are comfortable with yourself, you don’t feel like you need to make an impression on someone else, and (most importantly), you aren’t needy.
In fact, being silent and letting the other person talk is an incredibly powerful way for the other person to invest in the conversation with you. It will open them up (if you listen), and give you even more material for great conversations. It’s also good for negotiating, but we won’t go too much in depth with that here.
Another thing you can do if you really want to talk, the other person isn’t talking, or the person is waiting on you to make conversation, is to use the word association technique. You won’t ever not have anything to say if you remember this.
Remember: you don’t have to use that technique. Psychologically speaking not blabbering on and on talking about something that the other person doesn’t care about is probably more important than always having something to talk about.
This leads us to…
“What if we don’t have anything in common?”
Probably associated with awkward silences, not having anything in common can be a big drawback to having a conversation with somebody.
Say you want to connect with someone but you can’t find any real point in common with interests, conversation topics, whatever. What do you do?
Again, before I jump into techniques for finding something in common and connecting with them, I first want to talk about the psychology behind this question.
If you sincerely feel that you don’t have much in common with someone but you are still trying to connect with them (say, for example, they are pretty or handsome), what might be encouraging that desire?
Obviously there are multiple answers, and I won’t go into all of them right now. But one of the big ones, again, is neediness. Stop right now and imagine yourself totally content with your life: the people you know, your job, your relationships, your trajectory, all of it. Imagine being totally happy with everything you have right now, even grateful for everything you have.
Now imagine meeting someone new for the first time. They’re cool, but you aren’t connecting with them as well as you imagined. Maybe you thought they were attractive, but it turns out that you don’t have that much in common, your sense of humor is a little different from theirs, etc. What do you do?
The totally content, happy, and grateful version of yourself probably shrugs it off. They probably aren’t worth your time. Why would you want to add another person to your life that you can’t really share anything with, whether it’s an activity that you like to do together, or a deeper sense of values that you share?
Are you starting to get the frame that I’m describing?
Obviously, being content and grateful for what you have in your life and the relationships that you already have delves a little too deeply into other topics not meant for this guide. But the point is that by being able to come from a place where you overtly looking for confirmation from someone else is extremely powerful.
That being said, on a practical level there are several things that you can do to find what you have in common with someone.
As we talked about in the section “Connecting on a deeper level”, try to use conversational hooks, but specifically to find out more about what is important to the person and why they do what they do.
For example, I had this conversation last night:
Me: “So, what do you do for a living when you’re not playing drums?”
Guy: “I actually drive a forklift around and move boxes. It’s cool.”
He drives a forklift around. For a split second I thought to myself, “Shit. I read books, do yoga, and am interested in philosophy and comparative religion. What do I have in common with someone who drives a forklift?”
Then I got deeper.
Me: “Cool. I don’t know much about driving forklifts. What do you like about your job?”
Guy: “I actually get a lot of free time, especially in the winter when we aren’t busy. I usually use that time to read.”
Me: “Sweet. What do you like to read?”
Guy: “I’m actually a huge American history nerd.”
We got to talk about what was actually important for him. Instead of simply talking about his job, we actually were able to have a more in depth discussion (and I learned that Japan actually covertly bombed the US in WWII!). We connected on a deeper level, and I seemingly had nothing in common with this guy.
So what happened?
Like I mentioned, using conversational hooks will get you far. For example, last night I mentioned that I paradoxically learned more about American History while living in Spain than I did in high school. It was funny, people cracked up, and now there is this wide-open doorway for me to talk about living in Spain.
Another route is obviously to keep talking about American History, and ask specific observational questions. When I said that I learned about Japan and WWII, that actually came from a question that I asked him (“can you teach me something about American History that I don’t know?”)
The mindset as a whole should be constructed around being interested in the other person. This will help you ask interesting and authentic questions that engage the other person.
“How do I enter a group conversation without seeming weird?”
Maybe you want to talk with a couple of people sitting in front of you on the subway. Maybe you’re at a networking event or a party and there are a group of people huddled together smiling, laughing, etc.
Scary, right? You wouldn’t want to interfere with their conversation, right?
Well, maybe. There are times when it can be very strange when one person barges into a booth where a group of friends are hanging out at a bar. This has happened to me a few times. Though I’m usually pretty nice about this type of stuff (talking to people who are by themselves at a bar), most people aren’t.
As we’ve talked about, this depends on the location.
Networking event? People are supposed to meet other people at networking events.
Party? Same thing.
Bar? Kind of the same thing. It really depends on the moment, the situation, the people, how open, relaxed, and not needy you seem.
Apart from the conventional ways to start a conversation with another person which we’ve talked about (and which actually work great with a group as well), there are a few things you can do.
- Mention something that the group is talking about
This requires a little bit of eavesdropping, but here’s how it might look:
There is a group talking about a sports game that happened this weekend..
You: “Sorry, I don’t mean to intrude, but are you talking about the game this weekend? That was crazy!”
The group is talking about the food at a party…
You: “Hey, are you talking about the cookies? Those things are insane! Where’d you get them?”
This can also take the from of a clarification:
Someone in the group is describing something technical…
“Hey, sorry to butt in, but I heard you were talking about X, would you mind explaining that again?”
“I don’t mean to interrupt, but what time did you say the show is on tonight?”
- Ask to be introduced
If there is someone hosting the event (say a party, meetup, etc.), and you know the host, it usually isn’t out of place to ask them to introduce you to someone.
You might say something like, “Hey this looks really cool. I’m not sure I know too many people here, though. Is there anybody that you think I should meet?”
This is very simple, very direct, and being introduced with a warm welcome will only make the other person more receptive to you.
Final tip: coming out of left field with a conversation topic that the group isn’t talking about, or interrupting a group conversation (especially if it seems like a group of friends that all know each other) doesn’t go very well in my experience (and with people that I’ve worked with).
And the final question:
“How do I start a conversation and connect with a VIP?”
While this topic is a little bit beyond the scope of this guide, Primoz Bozic, an entrepreneur that helps experts build their own online businesses, wrote an excellent piece about connecting with VIPs at events and online groups, and how to build a relationships with them. He even digs into how to turn these VIPs into mentors.
I’d like to share some of the best mindset advice when it comes to connecting with VIPs that Primoz shares in his guide.
“What I try to do when I meet awesome people in person is two things:
- Be unique
- Connect with them on a personal level
You should always strive to do something that others wouldn’t do that will make people remember you and stand out form the crowd. That can mean recording interviews, bringing them personalized gifts, writing a blog post about the insights that you got from meeting them or another unique way of adding value.”
He recommends brainstorming 10 different ways you can be unique for a specific person before you even meet them. And finally, he also mentions that connecting with them on a personal level is key, for his sake and theirs. Connecting with VIPs and “awesome people” on a deeper, more personal level sets you miles apart from other people who only have one agenda: connect with the VIP for their own selfish reasons.
Remember how we talked about starting conversations with a huge, one-pointed agenda? Don’t do that. Connecting on a personal level is a breath of fresh air.
To read Primoz’ entire piece (which I HIGHLY recommend), just click here.
If you have any other specific questions, be sure to email me at email@example.com 🙂
Okay. You knew this was coming. Reading this long guide might have been fun up until now, but this is where the rubber hits the road.
Before jumping into this, I would like to emphasize that you will get as much out of this as you put in. Of course, you aren’t going to become Robert Downey Jr. in five days, but you will be well on your way to constructing different habits, and becoming a more confident person. The goal of this is to be more comfortable in your own skin so that starting conversations with anyone, anywhere is something that comes naturally and fluidly.
First, let’s talk about HABITS.
Everybody should read this piece on habits and identity by James Clear. It is the most informative, bang-for-your-buck piece out there on how to make habits stick.
The core idea? That we focus on all of the wrong things when trying to implement change. While we focus way too much on other peoples’ perception of ourselves, as well as our actions that we are taking to implement, we are missing out on the most important element for sustained habit change. What is that?
Yes, the things you do are important. Yes, how people perceive you can reinforce a sense of identity. But the most important part for actually transforming your social life? Changing your sense of identity.
Having a ton of positive social habits will only get you so far if you still believe you are a shy, unconfident person on the inside.
So how to change your identity? This isn’t a piece on psychotherapy, but one thing I’ve noticed that worked for me is focusing on who I want to become. This means having a clear, not ambiguous image of the type of person that I wanted to be.
You remember when you were five and you wanted to be an astronaut? This is kind of like that.
If you start to imagine who you want to be, every step you take towards getting there will be much more powerful.
Little wins, like talking to the person next to you in line at the café, or having a longer conversation with your bartender, will serve to reinforce this sense of identity, and will be more substantive than simply doing the habits.
Sooner than you know, peoples’ perspectives of you, your actions will start changing, your perspective on yourself will start to change, and sooner than you know, other people will start to see you differently as well.
With that being said, let’s now jump into the five-day challenge. One last time, if you do not take action, this is all for nothing! It’s all brain food, and it will be gone tomorrow.
The Five-Day Challenge
Day 1. Mindset
Action 1: Take out a pen and paper, and for five minutes write down things you believe about yourself. I know, this sounds silly, but do it! Write as many things as you can! I’ll list some right here about myself to get you started:
- I’m a man
- I can’t survive without coffee
- I’m shy (I’ll admit it, I still am)
- I could never work at a corporate job
- I think people judge me when I talk to them for the first time
Try to get to twenty. It doesn’t matter how vain, trite, unexciting, or not revolutionary these are. The habit is just to start to shock you awake to who you think you are.
Action 2: Through the day, notice the identity you are taking into social situations. Examples:
- When you talk with your boss, are you trying to impress him/her?
- When you participate in class, do you get nervous because you feel judged?
- When you order a coffee, are you open to connecting with the cashier?
It could be any one of these! Keep this at the front of your mind all day: “Who am I being right now? And what does that person believe?”
Action 3: Later in the day, after you’re done with work and you’re home, when you have a little bit of free time, take out the same piece of paper and a pen and finish the following questions 5x.
“If I were less needy, I would _____________”
“If I was comfortable with who I am, I would __________”
“If I had 100x more social confidence, I would ___________”
“If I was the most charismatic version of myself, I would __________”
In a way, today is the most important day because it goes the deepest. I KNOW. It’s so easy to want to skip this. It’s so easy to think of it as bullshit. But this is on you, and if you don’t want to do this, then maybe this stuff isn’t for you. Day 1 on challenges like these is always the hardest, the easiest to half-ass.
Anyways, take the time, do the work, and come back to this page tomorrow.
Day 2. Low-Stakes Conversations
Now you’ve done some inside work, it’s time to start with some small wins. Nothing too big today, but the goal is to get your new habits rolling.
Action: Have a conversation with three strangers in a low-stakes environment. We aren’t talking meeting with VIPs or going up to the most beautiful person you see today. These should be conversations that have no agenda. They might start with passing side comments that you make to someone at a café, or asking someone at work how their weekend was and trying to take the conversation a little bit deeper than maybe you or they are used to.
The real key to today’s challenge? Go one step further than you usually go.
If you usually connect with the cashier at your grocery store, try having a deeper conversation with them. If you don’t usually say something more than “Hey, how are you?” try to go a little bit deeper.
Remember, these conversations should have no agenda. You are just making small talk, and if the opportunity presents itself to take the conversation deeper, or to joke around or tell a story, go for it! But no expectations.
Day 3. Longer Conversations
If you’ve been keeping up, you should have 4-5 small wins under your belt. You’ve decided on the type of person that you are trying to be, and you’ve taken some small steps to reinforce that new identity.
Today will be a little bit more challenging than yesterday because it’s building on what you’ve already done.
Action: Start a conversation with two strangers, and keep the conversation going longer than the normal “where are you from?” or “what do you do?”
No time limit, or anything ridiculous like that. Obviously you can start off with the typical questions I listed above, but the point is to keep the conversation going and to use a few conversational hooks or engaging questions to open the other person up. Maybe share an embarrassing secret.
Today is probably the biggest jump. Being able to have longer conversations with strangers will reinforce the notion that you can have a conversation with anyone on a deeper level for yourself.
Day 4: Deepening conversation
You’ve talked to strangers. You’ve had longer conversations with them (or at least you tried. Don’t worry if it doesn’t go well, this stuff takes time to change and it doesn’t happen overnight).
Similarly to the previous day, we are going to be starting conversations with strangers, but this time around we will try to deepen it using what we’ve learned in the section “Deepening The Conversation.”
Action: Talk to 1 stranger today. Ideally this is someone you don’t know, but it could be someone you really don’t know anything about. Using one or two of the techniques in the “Deepening The Conversation” section, try to find something in common and connect with the other person on an authentic level.
This might feel uncomfortable at first, but it helps to realize that people actually crave the opportunity to talk about things that are important to them. We all want to connect with other people.
A big part of today’s challenge is active listening. Make sure to be present, and not zone out while they are talking with you.
Day 5: Interrupting a group
Ah, at last you’ve made it. Chances are you’ve probably already grown a ton. Today might be the most difficult for some people, but don’t worry. It’s really not all that hard.
Action: Interrupt a conversation of a group of people that you don’t know and introduce yourself using what we’ve talked about in the Frequently Asked Questions section. Introduce yourself as well. Ideally this should be a group of three or more, as two people don’t really constitute an “intimidating” group.
And there you have it!
If these action steps were difficult to do, don’t worry. Just keep trying and working at the level where you get stuck at. Don’t worry about the later stuff until you feel comfortable with the challenge that you have.
If these are super easy, I invite you to think of your own challenges.
These could be:
- Stopping a girl or a guy on the street to tell them that they are attractive and that you’d love to get to know them better
- Making an authentic connection with someone that you respect (and that may be difficult to talk to)
- Starting a conversation with a group of friends or strangers on public transportation
- Telling a medium-long story to someone that you just met for the first time
The point is to give yourself some resistance.
If you liked this article, or you thought it could use some tips that I didn’t mention, or if you think there is anything to add, please feel free to email me at firstname.lastname@example.org
Also, if you are interested in taking your social skills and charisma to the next level, I work with people individually all over the world.
To see if it would be a good fit to work together, you can email me and we will schedule an initial, free skype interview.
One Quick Favor 🙂
Please, please, if you liked this guide, it would be awesome if you could do me a quick favor.
If you know someone who is looking to improve their social skills or is interested in self-improvement, could you please share this with them?
And obviously, if you want to, it would be really cool if you shared this on Twitter, Facebook, or with your email list.
Here are some things you could say if you don’t have much time and want a script:
[For my friends who are looking to LEVEL UP their personal and professional relationships]
If you’ve ever thought about you wanted to learn about how to talk to and connect with anyone, check out this free Ultimate Guide To Starting a Conversation With Anyone (It’s awesome).
What I took away:
- 3 ways you can start an engaging conversation with anyone, anywhere (bars, networking events, the gym, etc.)
- The biggest mistakes people make when starting new social habits
- The bulletproof strategy for never running out of things to say (and controlling the direction of the conversation)
You can get the guide here.
If you share this, feel free to tag me! And if you learned anything or want to share your experience with this guide and the five-day challenge, let me know by sending me an email to one of the emails I send out to my email list.
I’d love to hear what you think 🙂