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A guide to socialising for the socially awkward

26 May 2016

I’ve always struggled with social interaction. The thought of having to mingle with a room of complete strangers never fails to inspire apprehension.

How the hell do you go up to a stranger and start a meaningful conversation?

So I spent a few years, reading up on social behaviour and the art of networking. You know, the sorts of things titled ‘beginner’s guide’ or ‘book for dummies’. Though they provided valuable points, they always seemed to skip that initial step of greeting a new person. The step I needed most!

I’m apprehensive about talking like an expert on this topic. I am by no means socially adept and like everyone else I have plenty to learn and discover. But I wanted to share the observations from my own personal experiences with other socially awkward devs like me, who struggle with getting to know new people.

Enough of the preamble, what follows is my personal guide to social engagement:

Start Small

I can think of countless times where I’ve walked into a room full of people and have not been able to find someone I would be confident in approaching. Greeting a new person always seems to be the toughest hurdle.

Sometimes you could be lucky enough to have a sociable person approach you, and half the battle is already won. But more often than not, we awkward ones need to initiate contact.

I’ve found the best tactic is to start small. Look for people standing by themselves because, more than likely, they are in the exact same situation as you. Simply walk up to them and introduce yourself, start a simple conversation – What is your name? What do you do? Where are you from? Once the conversation is going, things tend to evolve organically.

If everyone is already in groups, try to approach the smallest group. Fewer people involved in a conversation generally means they are more willing to invite people in or actively include you in conversation.

Get to Events Early

In my experience, getting to events early is the best way to meet new people. Groups haven’t formed yet, or there might be people by themselves waiting for others to join.

It’s the perfect opportunity to introduce yourself and start a meaningful conversation. This works really well with the approach of starting small.

Greet Everyone

Once you’ve started a conversation or joined a group, make sure you greet everyone. Even if a person does not appear to be directly engaged in the conversation, introduce yourself anyway. There is nothing worse than being left out or ignored, from your perspective and theirs.

Remember Names

Make an effort to remember names. I am generally terrible at remembering names, so I try to repeat it as much as possible during conversation to ensure it stays fresh in my mind. (Hopefully not being too weird in the process.)

And make sure you get the name right! If you didn’t hear someone clearly, ask them politely again. As soon as they say their name, repeat it back to them to confirm. If you’ve gotten it wrong, they will tell you. It’s best to get that awkward moment out of the way early so you can avoid an embarrassing situation later.

Assume Nothing

This applies to your whole conversation, starting from the first greeting. Assumptions can lead to awkward or even unpleasant situations. Unfortunately, this is a real challenge, since stereotyping is a part of human nature whether we like to admit it or not – everyone does it to some extent.

Try to keep an open mind when engaging people. It’s impossible to determine someone’s personality, background and experiences merely via their appearance.

If you are unsure, just ask.

Ask Questions

Make conversations a two way street by asking questions of the other person. After all, how boring is listening to someone talk forever without giving you the opportunity to respond? When you ask questions, you invite other people to join the conversation.

If you don’t understand something, just be honest and ask. This also helps you avoid embarrassment later when you finally reveal you have no idea what they are talking about.

This is my list of questions, committed to memory, for helping a conversation become unstuck:

  • What is your name?
  • What do you do?
  • What does that involve?
  • Have you been here before?
  • Why did you attend?
  • Do you know many people here?
  • What are your other interests?

I’ve found that once a question is asked, and people are talking, the conversation will flow naturally.

Involve Everyone

Remember that others might be just like you – trying to find a way to enter a conversation. Even if they appear confident or aloof, do not assume anything. It may only be their way of dealing with social awkwardness.

Get people involved by directing questions at them, or opening the conversation up to input from others. Don’t take over conversations by being the only one talking.

Make a conversation about the other person, not you.

Act Like Yourself

Every article on this topic includes this point – and for good reason.

Be yourself. If you don’t, people will know. Even the shyest person can see through an insincere act.

Besides, if someone doesn’t like who you are, you don’t need to be talking to them in the first place.

Be Honest

If conversation starts going into areas you’re unsure of, then ask questions to clarify. Don’t be afraid to let people know when you don’t understand. They’ll appreciate the honesty, and it’s another way to get interesting conversation going.

Don’t try to oversell yourself or exaggerate facts. It’s better to be up-front and honest than to get caught in a lie later.


I’ll be honest – after writing this guide, I found my ability to engage in conversation with strangers increased significantly. I can’t pinpoint the exact reasons for this new-found confidence, but I suspect it has something to do with consciously taking my own advice.

I had the opportunity to get involved in a wide variety of social engagements related to my chosen profession. The Humaan team attended a web conference together, then I attended a few industry meetups – both with friends and on my own.

I set a personal goal of meeting as many new people as I possibly could. Though this guide isn’t groundbreaking in any way, each point helped me overcome my apprehension over the few weeks I was busy with events. I saw every engagement as a chance to better my social skills and hopefully get to know some amazing people, and well… I guess I can say, ‘mission accomplished.’


  • Start small
  • Get to events early
  • Greet everyone
  • Remember names
  • Assume nothing
  • Ask questions
  • Involve everyone
  • Act like yourself
  • Be honest

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