My Step By Step Mindset On How To Start A Conversation With A Stranger

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One of the most beneficial skills you can learn is to go straight up to someone and create a relationship that wasn’t there 4 min ago. Can you imagine the possibilities that you can achieve with such a skill?

We will stop imagining and start achieving

Every single person had at one point in their life an encounter that lead to a conversation with a stranger, be it small talk or a full conversation, not forced but natural.

When something comes out of the blue and breaks that surrounding routine, you see people coming together, striking conversations, discussing whatever happened, and stretching the conversation to more general topics or even personal.
This communication comes naturally, not forced, panicking, no fear feelings, just discussing things in pure calmness.

Do you recall an incident that happened in front of you that broke the routine and everybody alongside yourself came together to discuss it?

We will start from here.

When we understand that this behavior is natural, people don’t have a problem with speaking with strangers, it’s our mind that creates the illusion of obstacles that stand in our way. Like the perception of bad events that might happen, the bad self-image that we run in the backs of our heads, and the thoughts that we give in to, that put us in a paralyzed state unable to act.

You are not going to be an expert in a skill when you do it once and stop doing it again, let’s agree on that. Think of any skill you’re good at, whether at your work or in your everyday life, remember how did it feel when you started doing it, and how it feels now.

Just like any other skill, only practice will elevate your communication skills and make you the expert in starting conversations with anyone.

It is happening, there is a potential someone, and you want to be talking to that someone.

We start by observing the surrounding, creating a scene in our mind, this scene has us, the person to talk to, and everything concrete in it.
We need to minimalize surprises as much as possible, so start by answering these questions:

• Is the person busy or free?
• Is that person surrounded by people, or alone?
• Is it a crowded area with too much noise or it’s calm?
• Is there anything interesting happening within our field of view?

Then give this a quick thought, from now to 5 min, will the answers stay the same?
if they change, how?

Let’s go back to the unnatural event that broke the routine example. You have your scenery ready in your mind, if something suddenly occurred, you know for sure with all the confidence there is, that you can go talk to that person inside your scenery with no problem whatsoever and it will be naturally calm and rich.

We will create that same environment without the sudden element.

The reason a third-party element make things work is that it gives us a reason to talk, something to discuss, and discuss in detail, it will also give us things to follow up on our initial approach and make it last.

We are going to create these elements ourselves now

• A reason for approach
• Something to discuss, and discuss in detail
• Things to follow up with

The hardest thing in approaching a stranger and starting a conversation is the reason, or what you like to call, an icebreaker. Finding a good reason alone might be a challenge, and since every single person is different, there might be a chance that this person is not on par with you on that reason but this should never stop you because if you believe in your reason and truly believe in it, you will make it as convincing as needed to even change the perspective of the other person. Let’s get to it.

There are two types of reasons, a direct honest approach, and what I like to call a situational benefit approach

• A Direct Honest Approach

When we speak of a direct approach, it is very straightforward, you are stating your intentions.

For Example:

• You saw someone with a really killer outfit, you approach them, tell them that you love the outfit, you might want a similar one for yourself or to buy as a gift.
• You are at a presentation the speaker said something really interesting that stayed with you, you go at the end and tell them that and discuss it.
• You are at a party and someone is dancing in a way that you loved and found unique, you go tell them that and ask how did they reach this state
• You like a person and want to talk to them, you go tell them what features you like about them and proceed to talk.

The examples are endless here, it is the most honest straightforward way, however, you might be shy, worried, or afraid of rejection, and you don’t want to state these intentions if they are too personal like if you like someone and want a more subtle approach where things feel like it just happened. This is where we go to what I like to call

• A Situational Benefit Approach

This will be harder to achieve because it varies from one scene to another. The scene that you created in your mind when you were observing

I personally absolutely adore this type of approach, because it is unique, challenging, chaotic, original, and so on. I love it, it starts very uncomfortable and weird but the more you do it, the more natural it becomes and comes spontaneously to you

The intention here is to use the scene, to create a scenario where you are talking to that stranger, let’s get to it

We are going to start from the observing and analyzing step, we created the scene, understood the variables, spotted if anything interesting is happening in the field of view and we are going to use that interesting something.

The only way to explain is by examples:

To start in its simplest form think of two people running the same road, with their dogs, the dogs will at one point come together hence giving the owners the opportunity for a small talk. That is using an external factor that could’ve easily not been there to give a reason to talk

You are at a birthday party, or a business meeting, everybody there has something in common, be it the host that their birthday is today, or the main subject of the business meeting, the food they all eating, the music they all listening to… that something that all have in common is a great reason for you to start topics at these events

If you are in a touristic sight, you can ask for directions, or something specific as a reason to start a conversation

If you are in a park, or any public place, your reason for approach could be anything that is strictly related to that place, like does it get crowded? are kids allowed? at what time do they close? etc.

There are endless examples but you only need the logic, this is just the reason you came and started that conversation with that person, it doesn’t have to be complex or deep, it could be as simple as eye contact that started the conversation, this is only step 1 of the plan

The reason for the approach is only the icebreaker, something to discuss is what’s going to kickstart the conversation.

If you chose an honest direct approach as your reason, your something to discuss is gonna be way easier, let’s use the previous examples:

•  If you had approached someone for their outfit, you’re going to be discussing their outfit, what do you like, and what info you want from them
• If it was a speaker, you’re going to discuss the speech
• If it is because someone has killer dance moves, you’re going to be discussing the moves and where did they learn to dance
• If it was someone you like, you’re going to compliment what you liked and lead on with it.

It is fairly easy to follow up when you’re being honest, the hardest part was being honest to start with so if you had chosen the second approach you need a bit of planning.

If you used a situational benefit approach, it means, for the most part, you’re discussing the surroundings, but we both know, your interest is not really in the surroundings, it is in the person.

Before approaching ask yourself:

• Why do I want to talk to that person?
• What do I want from them
• When I finish the conversation, what do I want to have accomplished?

When you answer these questions, you have a target for that conversation, so when you’re done with the opener, you know how you’re going to lead it, and that takes us to step 3, the contingency plan.

You created a reason to talk to a random person, and you set a goal of what you need to accomplish with that talk. To seal it, you need to have backups just in case things didn’t go as planned, which will, because people are unpredictable, and that’s the beauty of it, every scenario is different and presents new challenges.

Having things to follow up with simply means having backup topics to discuss, just in case your main ones failed.

let’s say the main topic that you wanted to discuss wasn’t an interest for that person, or the person didn’t have the knowledge to answer your questions if you opened up with them. It’s not like you’re going to create a checklist of questions for them and see what works no…

It is simply going to be a few alternative options that you might go in their direction, in case the main topic wasn’t on par with the other person.

Since each situation needs different main topics and different things to follow up with, I can’t just state random things, instead, I will go with some key things to do to assure yourself you are ready in any situation.

A general follow-up would be a compliment, you compliment appearance, possession, or behavior, so if you can’t find anything to follow up with, follow up with a compliment, and don’t just state it, explain it and tell them why do you believe it.

Read more. Be mindful of the news, whether it be local, political, tech, health, new scientific breakthroughs, or new products. All of these will widen the range of topics you have in your mind that you can use to fill in the gaps, follow up on your topics, and invoke their curiosity over things they didn’t know about. If you have their curiosity they will be needing that conversation to continue and they will be the ones actively trying to keep it.

Now we finish creating the plan of approach, one thing to keep in mind is that whatever your go-to plan is, it is going to be the first impression, so avoid personal and inappropriate physical comments, alongside negative thoughts.

One more obstacle arises before the action, we discuss it next

As soon as you start thinking about striking up a conversation with a stranger, your mind will start working against you, thoughts of doubt, doubts about what you’re doing, why you’re doing it. Thoughts of perception as to why that person wants to talk to you if they are busy, and a million ideas revolving around one target. To stop you!

But you’re not going to stop now are you? you just read 2000 words not to stop now…

I can write an article (and probably will) about how our brains are programmed to keep us in our comfort zone and not allow us to do things that aren’t in our daily routine

What you need to know is that these thoughts are normal, we all feel them, from the most successful to the beginners, what’s different is how you tame them.

When you know that these thoughts are normal, it is easier to control them, you have created a killer plan of approach, and armed yourself with all the topics you need to have a successful and fun conversation, there is nothing to worry about.

Visualize yourself from a third-person view going for it and imagining it a success, don’t overthink it much, and don’t go down that chain of multiple scenarios. You have the plan, you have the backup plan you are ready to go, the more you think the less you will do, just go for it.

It is a good time to mention meditation here. Being able to focus on the breath in any given situation and be present in the moment will be a great help towards overcoming the mental barriers and the fear that will arise as soon as you think of approaching someone. Being able to identify these thoughts as harmful will put them to rest and stop them from stopping you, meditation does that!

There are lots of factors that may lead to failure that are out of your hand, the person might have their significant other next to them and might panic, they might get nervous and reject you, they might be in a bad mood and not in the mood for people altogether, they might be in a hurry, many many scenarios but you do you, your plan and commit to it, believe in it, don’t overthink it and remember that if they reject you it’s a thing in them, not in you. You did a great job by committing to this

Let’s talk about confidence. If I want to put a secret behind successful conversations, it is going to be confidence. You can talk nonsense with confidence and people will go with you and try seeing things from your perspective.

Confidence is like 80% of the job here.

The good thing is that most people can’t read other people well, so if you’re not confident, just fake it, act confident, few will tell the difference and with time you’ll become more confident

Let’s start by approaching the person:

• Have a straight relaxed posture
• Smile on your face
• Act calm (I know you’re not), don’t do things in a rush, take your time
• Make sure that they see you before you approach them, don’t surprise them
• When you’re next to them, keep the stranger’s distance, don’t go too close
• If the landscape allows you to be a bit more down in comparison to them, go for that spot

These key steps are there to ensure that you show good self-esteem and confidence, while not looking threatening.

People already build an impression of you just by observing you, and for the most part, they believe it so it’s important to have the confidence and self-esteem high to get that predefined judgment positive

Now you are finally speaking to that person!
Remember your plan, act naturally, and if you forget something, don’t panic, just go for another thing, we created backups just for this moment.

During the conversation, whether it’s brief or long, we need to pay attention to a few things:

• Always observe the other person, don’t stare, just observe, body language will tell you all the things they’re not telling you verbally. No need to be an expert here but reading the most general cues will help you immensely in identifying a topic, a compliment, or an approach that was perceived as bad, and that knowledge will put you one step ahead and you will be able to correct it before it does any damage to the conversation.
• Listen to them, don’t just say what you have to say as a rush of information, listen to their response and let that response flow through the conversation
• Sometimes the other person would be shy or nervous, and unable to get that conversation into a good flow. Don’t take it personally, you armed yourself with various follow-ups, try and see what works
• Make sure that your questions and subjects are open-ended and ask for an in-depth response, in short, they can’t just be closed by a yes or no answer.
• Do not jump from one topic to another, squeeze in every topic as much as you can before transitioning to another

Whatever you do, remember that there will always be communication barriers between any two human beings because each person perceives things in a different way than the other, so it is recommended to stay calm, be wiser, and try different approaches to the same thing.

If you feel that the conversation is not kicking it is worth mentioning that the other person might not be interested at all but doesn’t wanna be rude so if you notice that this is the case it is a good practice to end the conversation politely and nicely, saying it was nice to meet you and good talk and move on.

If the conversation kick in and everything goes as planned it is important to convert the initial opinion they got on you into something better no matter what it was.

You are in control here, and you don’t need me to tell you what to do, but I’ll throw in some tips:

• Get their name, make sure you repeat it correctly, and don’t use nicknames without their consent
• Focus on listening rather than speaking about yourself, give them the space, let them speak
• Be understanding, don’t judge, and don’t overreact
• At times repeat some of the sentences they are saying to assure them that your focus is with them
• Use the words our, us, and we more often to make it more personal
• Observe any cues in their stories that you can use to keep the conversation flowing, catch their interest by taking what they’ve already mentioned as an interest
• Don’t ask about specifics too soon, keep your questions generalized and not targeted unless they mention something specific then you can ask them to elaborate on it
• Do not compete with them over who has a better story
• Don’t speak for too long before passing the ball
• If the conversation goes on longer than small talk, you need to consider sharing something personal, not too personal, but just enough to make a better connection

Your body language must match your attention, meaning keep eye contact without staring, don’t get distracted, be free and don’t look tensed, nod, express with your arms and maintain a good posture towards them, and most importantly… Smile, you are acquiring a new skill by practice

A good point worth mentioning is that we perceive the world in our 5 senses, we see the world, hear it, feel it, smell it and taste it. Some people emphasize one over the other. During the conversation, some would use I picture you, more than I feel that, so they perceive it through seeing. Being able to identify how the person perceives the world and match it using the same words will create a better connection.

No matter the way this talk came into motion, it is going to end, so it is important to end it in the best way possible.

Depending on the reason behind you approaching a stranger this ending might require a ‘catch up with you soon’ ending rather than a stale ‘goodbye’, you already have that in mind when you were brainstorming what to discuss in detail, so we’re good we know what we want, we just need to make sure we act upon it

When you’re leading the conversation to its end, compliment the other person for their good sport, appreciate the time they gave you, thank them for the interesting conversation and throw in a thing they said during that conversation that made your day, or simply you liked.

After that you need the follow-up, ask them if they’re interested in doing this same thing again, and their preferred method to communicate that, and make sure you got that info correctly.

Don’t forget to congratulate yourself on your success. You put on a plan of approach, believed in it, committed to it, bypassed its mental barriers, made someone’s day and it worked. And you read through all this article… Woow

Let’s be real, not all the approaches are going to be a success story, so we need to prepare for that as well.

Overcome the fear of failure, visualize the situation going south and you dealing with it, it will help you be more prepared when it happens.

If you get rejected, go tell your friends about it and laugh it off, make it a joke, it will ease it up.

If you got rejected in a bad way and it wasn’t something you actively did, strike a joke about it, even joke with the surrounding people that their attention was caught, they will see that you weren’t affected by it and your self-esteem is high and bit by bit this behavior grows your chances of success.

Always have positive thoughts, positive visualizations, and nice things in mind when doing this, because this will indirectly show a positive body language which is crucial for the first impression the person will have on you

When you do all this, I want to hear about it, tell me in the comments all your success stories, as well as the failed ones, let’s discuss it, laugh about it together, and create better scenarios

And if you still feel like you need an extra push, I offer life coaching sessions where we overcome such barriers. Feel free to check that out or simply contact me.