How To Start a Conversation With A Stranger

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Want to up your social skills? Have the confidence to approach a man at a bar? Strike up conversion with people when out and about? Then my friends, you’re in the right place! Here’s how to start a conversation with a stranger. 

See, whether it’s to build your own confidence, or as a secret task within the ultimate singles dating challenge – the benefits of starting a conversation with a stranger make it well worth it.

So let’s start from the top, shall we? Begin with the basics? Break it all down to make this far easier?

How To Be More Approachable

Before we jump into how to start a conversation with a stranger, I want to first quickly run through what makes a person more approachable.

This will not only increase the chances of someone starting a conversation with YOU, but it also makes it far easier to start the conversation because you’ll have formed a teeny bit of a connection.

See, body language is absolutely key. And what you give off, you’re more likely to get back. This is therefore essential for forming the ‘foundations’ if you like.

So, your tick-list to start building on is as followed…

1) Hold Your Head Up

Try not to be glued to your phone because it will stop you from being aware of people around you and stop you from connecting.

You also need to have a little confidence, and be able to get that eye contact (which we’ll move onto next!) so try to avoid looking at the floor, your feet, your hands.

Instead, walk with your head level or higher.

2) Get Eye Contact

You don’t have to completely STARE SOMEONE OUT, that would be freaky. Ever wondered why he’s staring at you so intensely? Yeah. You don’t want to do the same thing…

But in order to start a conversation with a stranger, they need to be looking at you (well, they don’t need to as such, but it sure makes it easier.)

To encourage this, start by looking at them. Or, if they’re already looking at you, hold their eye contact back. Be friendly.

When you do actually reach the point to speaking to them, it’s also useful to know that as a rule, you should try to keep eye contact about 60% of the time.

If you find direct eye contact difficult, you can overcome this by looking at only one eye at a time, or at a spot between a person’s eyes. They won’t actually be able to tell the difference. Handy huh?!

How To Start a Conversation With A Stranger


Smile at strangers. Smile at people you’d like to speak to. Gee, smile at those who you feel like there’s NO WAY you’d get a smile back from!

Because why on earth not?! Feel awkward? Embarrassed? Don’t! You’re just being friendly. It’s a good thing. It’s a nice thing!

And did you know – when you smile, your brain releases tiny molecules called neuropeptides to help fight off stress. So it actually makes talking to a stranger feel EASIER!

To get used to it a little more, start by smiling at strangers when walking. This is easier as you know if you don’t get a smile back, you can just carry on walking (ha!)

Once you’re in the habit of that, then start smiling at people you want to speak to in places that you’re more able to strike up conversation. Like on public transport, at a bar, in a park.

It creates a great starting base to then start a conversation with a stranger. Smiles are also great to add on once you’ve got their eye contact, like we mentioned above. So it’s a little like…

  1. Look up.
  2. Grab eye contact.
  3. Add a little smile.
  4. Annnnnddd… initiate conversation.

Simple huh?! What other things can you do to be more approachable before we move on? Well…

Three Quick-Fire Tips

  1. Avoid blocks. Like your drink held in front of you as opposed to at the side. Keeping objects between you and others makes you appear guarded and closed. 
  2. Use open body posture. Like having your hands down at your side, instead of crossed over your chest. Or your shoulders back instead of slouched.
  3. Angle towards them. Watch your feet, your legs, and your body. You should be angling toward the person you are talking to (or want to speak to) – not away. 

Become aware of the little things, because it will then make the big stuff far easier.

How To Start a Conversation With A Stranger

How To Start a Conversation With a Stranger

So now we’ve got that out the way – you’re fully prepped and ready to go! So what are some simple openers that will make it far easier to start a conversation with a stranger? Here’s 5 to get you started.

1) Comment On The Situation

So for example, let’s say you’re at the bar and are waiting to order, don’t say the obvious about having to WAIT (this just comes across as negative!) Instead you might like to say something like…

“Wow, those cocktails look amazing don’t they?! What are you having?”

Or let’s say you’re on a walk and you both kind of swerve to avoid each other’s paths, pick up on this and use it as a chance to say something jokey.

The KEY however with this one, is to say something that still encourages or requires an answer. So you might build on this further with something like,

“Nearly a bit of a collision there hey! It’s a beautiful day though isn’t it?”

This leads me onto my next easy opener to start a conversation with a stranger…

2) Talk About The Weather

It may not be the most imaginative or inspiring, but it’s comfortable territory, familiar territory, which makes it a great opener.

And hey, this can just be a nice friendly start. You can build on it…

For example, if you’re out and about, bring up the weather and tie it in with the fact that it’s too good to stay in on a day like today.

Or if it’s a bad day, you could say something jokey about the two of you “braving it” but mention that you don’t like to stay in.

You see? The weather opener can just become a base.

To bulk it out and turn a comment into a conversation, you can continue it with a question to ask someone you’ve just met or complement it with something more personal.

3) Ask a Question

A great way to start a conversation with a stranger is to ask a question. Questions that are easy to ask are usually un-intrusive, an “excuse” if anything.

So for example asking for directions, asking for recommendations.

You can still ask these things even if you live in the area (and have lived in that area for your whole life!) Like,

“I’m sorry but could you please help me settle a debate here!? Where do think is the best place for tapas in CITY NAME?”

This is more verging on asking for an opinion. It’s just sociable and fun!

Obviously some questions will be easier to ask in certain situations – like you wouldn’t ask a stranger walking by what his favourite bar is, just randomly out of the blue!

But in almost any situation, you can find a relevant question to strike up some conversation! I mean, think of the interesting questions you ask friends even, if you want safer territory.

How To Start a Conversation With A Stranger

4) Pick Up On Something Personal

Everyone likes a complement so the best way to go about this one, is to give exactly that! Notice something you like about the person and say something nice. For instance:

  • The clothes they’re wearing.
  • A piece of stand-out jewellery that you really like.
  • Maybe a t-shirt that shows an artist or musician they like. [Common interest]
  • Or perhaps they have an interesting tattoo you can complement and ask about.

You don’t have to go all out with personal questions to ask a guy just yet. No, this would be far too much as a conversation starter!

But you’re just noting something small and personal about them.

Please note – it doesn’t all have to be physical either. I mean, you could complement the fact that they’re hiking with ease if you’re out on an adventure.

“Damnnnn, you are putting me to shame over here! Where do you get all of your energy from?!”

Want to steer clear of the complements? Then instead, say something of interest. For instance…

  • If someone’s reading on a train, ask about the book and say about something similar you’ve read. (Maybe you actually have, too. Maybe it’s one of the best books for singles. Now THAT would be a pretty cool conversation starter, right?!)
  • Or let’s say they’re sat opposite you on the train, just take an interest in them, “heading anywhere nice today?”

Whatever you say, if you say it with a smile, you’ll be amazed at the difference in response that you might get back.

5) Say Something Cheeky

Last but not least, if you want to start a conversation with a stranger – particularly if it’s someone you kinda fancy, you feel the chemistry and you’ve been reading their signals and seem to be getting those vibes back – then be bold and brave!

See there’s ways to tell if someone is flirting with you, and you can then build on this with a cheeky chat up like or a flirty comment.

Here, let me spam you with some funny ones to finish…

  • “Hey, please keep your distance. I might fall for you!”
  • ‘So aside from being sexy, what do you do for a living?”
  • “Nice shirt! Is it made of boyfriend material?”
  • “I think I’m lost. Can you give me the directions to your heart?”
  • “Is it hot in here or is it just you?”
  • “Do you believe in love at first sight—or should I walk by again?”
  • “It’s a good thing I have my library card because I am totally checking you out.”
  • “Do you have a map? I keep getting lost in your eyes.”
  • “I just lost my phone number. Can I have yours instead?”
  • “You’re so handsome. Can I tell that to you again this Saturday over drinks?”
Flirt With a Stranger

Have Fun With It

Whatever you decide to do, have fun with it! Go into it with the purpose of upping your confidence, maybe meeting some new people and having some more stories to tell!

Remember, if you’re single and doing this open-mindedly for an alternative to using dating apps – men are looking for ways of meeting women too, so they’ll actually be THANKFUL if you can strike a conversation with them!

Of course, always go into it with 0 expectations (and therefore no pressure or disappointments) but that’s when you may actually end up then being pleasantly surprised with what comes from it. You see?

So, take care. Be strong. And be happy! Because this is an exciting time of life!


How To Start a Conversation With A Stranger
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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