Talking To Random Strangers In Singapore



When I was in Bayuex, a small town in France a couple of years ago, I made a very interesting observation. The people there were not only gleefully happy, but they were all talking. Not just to their friends, but to everybody. 

Everyone was everyone else’s friend and there were people stopping me and asking about me and where I was from, or giving me suggestions to places I should go to or eat. It’s not that hard to bring the practice to our sunny shores with some guidelines and an open mind. 

So let’s make a change, infuse some warmth into your day and to your fellow man. Who knows? If you all follow these tips we might see a different Singapore. Or at least, Singapore will be different to you.


– The Basics Of Talking To People –


1. Smile!



The first step to radiating happiness is to be happy yourself. Smiling makes you more approachable, relieves stress and promotes a healthier mindset. So take a second or two and give yourself a wide grin in the mirror before you leave for the day you gorgeous devil!

Next, practice that dashing smile on passersby, the auntie at the coffeeshop, Muthu from the mama shop, anyone you come across. Don’t worry if they don’t smile back, you’re just having a great day and nothing can get you down – which is yet another reason to smile!


  • Spend a couple of minutes just before you leave practicing that smile in the mirror.

What NOT to do

  •  Don’t force a smile – it’s obvious and weird uncle creepy.
  •  Don’t hold it for too long 2-3 seconds max then tone it down. 

2. Greet People You See



Just start by saying hey! Or good morning. It’s so simple but so many of us fumble over it. Couple that with that killer smile you’ve been practicing and you’ll be an unstoppable force! Who would say no to a warm greeting like that? 


  • Maintain eye contact and smile to 3 passer bys on your way to school or work.
  • Step it up and say good morning or hello to them.
  • Say hi to that cute guy/girl the next time you’re out at Zouk. 

What NOT to do

  • Engage them from behind! Chances are you’ll scare them.
  • Stare for too long. Eye contact is great but not too much.
  • Be half hearted about it. You’ll be met with a lukewarm response if at all. Don’t be shy, just say hi!

3. Compliments



There’s something good in everyone. The best way that I have found to start a conversation with anyone is to give them a compliment. Love those pumps? Let her know and ask her where she got them. If you take it far enough you might even want to ask if she has a Zalora discount code for cheaper ones.


  • Go out and spot things about people that you like.
  • Start with a greeting then tell them what you like about them.
  • For added bonus and maximum effect, compliment them on a non-superficial trait. 

What NOT to do

  • Go overboard. Stick with one compliment, going overboard will make you seem like you have an agenda. 

4. Be Autonomous



You’re going to meet all kinds of people: an ah beng from the neighbourhood school just down the road, a scholar from a top school, or you might even find that the uncle who has his morning kopi at the coffeeshop downstairs is a wealth fund manager! They are all going to react differently. You’ll have memorable conversations, make new friends and connections, receive utter silence, or be rudely dismissed. 

But hey if that happens just pop back to remembering how great you day is and how you’ve already given them a story to tell their friends. 


  • Every time you get a negative reaction, think about your state of mind vs theirs. Realise that you’re better off staying in a social mood then join them down there in gloomsville. 

What NOT to do

  • Get hung up over bad reactions. Move on if they aren’t receptive, because there are other people waiting to receive your gift of warmth.




– Advanced Conversation Skills –


1. Observe and respond



So you’ve said hello, what’s next? You could straight up ask for what you want to know, “what do you do?”, “what’s your name?”, “where are you from?” etc. But a better and more fun way is to observe and make an educated guess – you’ll reduce the risk of sounding too kaypoh.

How are they dressed? How do they sound? What was their reaction to you? All these are clues to who they might be. Rainbow hair and spiked heels? She’s probably in a creative industry. Dressed in all white? Maybe some guy working for PAP… or the KKK. 

Observing and responding shows someone you’re genuinely interested and that you’re paying attention to them. Which is always a nice feeling. Don’t worry if you make a wrong guess, chances are they are going to be curious about why you made the assumption, which leads to yet another conversation.


  • You can practice this with a friend and use your observations about them to carry on a conversation for 5 minutes.
  • Play this game with your friends, pick one guy out from a crowd and guess what he does. Then go and ask him. Winner gets a free drink. 

What NOT to do

  • Press the interaction if they aren’t receptive to it.
  • Don’t point out anything embarrassing eg: “Excuse me, did you just come from the gym? Because I can see your armpit stains on your shirt!” 

2. Ask Non-Lame Questions



In my experience, it’s always better to engage your right brain for conversation. So use it! Ask open questions. Questions like “have you had dinner?” or “what do you do?” illicit very straight forward and programmed answers. Instead try “how did you feel about your dinner?” or “what’s it like working in a restaurant?” 

The more observant readers might have noticed a pattern in the questions, and the key is in feelings. Feelings are controlled by the right side of the brain and engaging someone in an emotional state is often more interesting than engaging their logical brain. So try it out and you might be surprised by some of the replies you get.


  • This is an old improv game but it’ll work. Get a friend and only interact using questions. You aren’t allowed to make statements! It’s actually pretty hard but it’s a lot of fun.Eg:

You: Where is my Tau Huay? Him: Weren’t you on Tau Huay duty today? You: Can’t you just give me a break? Him: Can you take our Tau Huay break more seriously?

What NOT to do

  • It’s fine to ask straight questions sometimes but don’t do it more than once to prevent the intrusive or interview-like vibe. 
  • Ask personal questions like “Where do you live?” and just for the guys out there “Can I have your number?” Should not be anywhere close to your top 5 questions. Establish a connection first before asking for it, you’ll have an easier time.



3. Don’t Forget To Talk About Yourself 



While it’s true that everyone’s favourite topic is themselves, don’t forget that a conversation goes both ways! Talking about yourself also gives someone a stronger mental footprint of you. So stroke your own ego, toot your own horn, let them know what you care about and what drives you. Be open and they will be more willing to open up too.

Don’t forget to put in some emotion into your speech too. Remember, always engage feelings.


  • On a piece of paper, write down 5 cool things about yourself or experiences you’ve had, or interesting facts about yourself. Experiment with different ways of expressing and talking about them. Make them emotional and engaging!
  • A good way to start talking about yourself during a conversation is when you can relate to something in your own experience eg:

Stranger: Yes, I am from a design school, is it that obvious? You: Haha yeah, I used to hang around design types all the time and we went on some crazy adventures, I remember this one time…

What NOT to do

  • Start telling them your entire life story and accomplishments or about the 5 Ferraris you have, 1 for every workday. 
  • Tell them that really embarrassing but funny story that puts you in a bad light. Yeah it’s funny and always gets a laugh, but save that for when you’re more acquainted. 

4. Be Natural – Forget Everything You’ve Learnt



Alright now you have the tools you need to go out there and make some good chit-chat! Your last step is to forget everything here. Social communication should be based on feelings and it ain’t gonna work out if you treat this like a checklist for all your conversations. 

Instead internalise these concepts and keep them close to your heart and let everything else flow. Speak with your heart not your mind.


Take the first step


So there you have it, I hope this list inspires you to get out there and take action. You never know who you might meet or inspire, and honestly since you have the power to do it now, it’s your responsibility too!

Go out there and rake up some smiles, talk to that cute girl in line, meet your new business partner, find out about a cool new bar and so much more. Remember the next time you hesitate about talking to someone interesting, you could be missing out on a whole lot of life.