How To Start A Conversation In The Street

Welcome to the second episode of The Vault. I’m going to be showing you the best way to start a conversation on the street with a stranger! I personally feel that a lot of people stop themselves from talking to strangers and making conversations because they think they’re going to mess up. But really these are the best opportunities we have for improving our social skills and developing our charisma.

My aim in this video is simply to show you how to approach people and not mess things up! So without further ado…

  • Mindset
  • Smiling
  • Pace
  • Thinking Positively
  • Getting Someone’s Attention
  • Playfully Persevering

First of all… before we get onto the best way to start a conversation on the street, I just want to cover a bit about the right mindset to have going into this. My mindset is that I always want a positive outcome from any interaction I have. When a lot of people start talking amongst one another, they don’t really attach themselves to this kind of outcome, and as a result, they come out with something that’s a bit irrelevant or indifferent; something that has no emotion attached to it. In order to fire up emotion in other people, you need to be the one who emotes (and asking where the nearest loo is, just doesn’t do the trick!).

If you want somebody to feel an emotion, you must first feel that emotion yourself. So have a positive outcome already in your mind, as if you’re already certain that isn’t going to go really well. Getting great reactions really is as simple as being positive.

Here are the first three things that you can really focus on when approaching people and making conversations.


I can’t emphasize how important it is that you smile when talking to new people. You have to remember that when you’re approaching people (especially in the street!) no one has any idea who you are, and in order for them to feel comfortable in conversation with you, they need to be sure you’re not a threat to them. To demonstrate this right off the bat, all you really need to do is put on a big, toothy smile.

‘Grinning is for wimps! Bust out a full on smile and commit to being happy.’ – JMC III

Don’t let this smile slip as soon as you’re in conversation with someone. You should be smiling throughout the entirety of an interaction. Don’t worry if it feels slightly unnatural or uncomfortable at first; it always does for anyone trying it. Smiling is something that I had to adjust to myself, and it took a while for me to fully get to grips with it. But just to reiterate the importance of smiling why not approach 20 people, 10 whilst smiling, and 10 with a straight face and just see the difference for yourself!

Talk Slowly

The next thing to make a note of is the pace at which you communicate. In this video, I actually talk a little too fast (be careful not to make this same mistake). When talking to new people, many of us get anxious in anticipation of silences. However, silence is your friend and shouldn’t be something that you ever fear.

Always Think Win/Win

In my head, when I go and talk to somebody, I’ve got two different ‘filing boxes’ that I put experiences and memories in. I think most people have these “mental cabinets,” and in my opinion, you actually get to label these cabinets yourself! I’ve chosen to label my two cabinets as, “This went really well!” (which is full of really fun, successful interactions and conversations) or, “This was really funny!”

For the second box, most people typically leave it on their default of, “This went really badly”. But by having this, you’re still leaving yourself open to a ton of negative feedback. What I’ve found is that the most charismatic people never have anything bad happen to them, because they choose to reframe it as something that was just a bit of a laugh. So my advice to you would be to change the label on your second mental cabinet to ‘This was really funny!’ The thing is, you only have two cabinets, so by doing this, any interaction you have from now on can only ever go really well, or be really funny! In my mind, there is no longer a cabinet for, “That sucked,” so I just end up with plenty of funny stories to share.

Now we’re going to look at what you actually have to say…

Getting Their Attention

The first thing to keep in mind is that you want to get someone’s attention before you launch into a conversation. Too many people will try making conversation with someone before that person’s even listening. By getting someone’s attention before you start talking, you don’t leave yourself susceptible to being in that awkward position where you’ve said something and they haven’t heard you.

Getting someone’s attention can be as simple as saying something along the lines of, “Excuse me”, or “Hey” followed by a pause until you have in some way been acknowledged.

Pacing Their Reality

The next thing I will do is pace their reality. What I mean by this is that you empathize with someone and say what you both see. If you’re going over to approach somebody and it’s really random, acknowledge that it’s really random! Doing this just demonstrates a kind of social intelligence. You acknowledge that what you’re doing is completely random, and by doing so, you put their mind at ease.

If somebody looks as if they’re in a mad rush to get somewhere, telling them that you appreciate that they are in a rush makes it more likely that they will stop and talk to you because they know that you’re not going to keep them there for too long.

Playfully Persevering

Your next goal should be to push through the next twenty to thirty seconds, which can often be the hardest part when approaching people and talking to strangers (especially if they’re British, apparently!). This is just because there is still that thought in the back of their heads that they’re interacting with someone completely random. For this short time period, you don’t worry about their reaction. You can get past it is just by pushing your enthusiasm onto them.

Hopefully, after watching this video you’ve gotten a better understanding of the best way to start a conversation on the street, and now what I’d love for all of you to do is go out and try this stuff for yourself!

Be sure to check out episode three, where I show you how to meet people in a bar!

Further Reading

“Confidence” by Rob Yeung