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The question I would like to discuss with you today is “Why is it impossible to break the ice with him?”. It’s safe to say that all of us might have experienced a situation of social awkwardness. Whether it was at a friend’s work party with no one we know, or a baby shower with plenty of new parents except you, we have been in a situation where we just simply feel that we don’t belong. It’s not like we didn’t try – we tried to start up a conversation and perhaps try to make some friends, but somehow we can barely get past the awkwardness, let alone breaking the ice. It just didn’t click. And then, we ended up hiding in the corner while eagerly looking forward to the end of the party. Well, in this episode, let’s figure out how we can tackle this kind of situation and prevent it from going the same way as how it used to go.

As a starter, I would like to call out a fact – and I can’t stress this enough in every episode – that everyone is unique with their own set of characters. There are a lot of psychology metrics and tests out there that can generate a simple classification of the human character, which we can use to understand characters and maximize them to our benefit. Myers-Briggs Indicator is one of the most popular one. It uses four to five combinations of letters to represent a certain character. Enneagram indicator is also widely used, which classifies humans into nine main types with additional tendencies towards a secondary type. In my experience, using these indicators as a basis of social interaction is a good place to start. Especially if you have been acquainted with the person for quite some time, hence are able to put the puzzle pieces together without having to ask them directly or shove the test to their faces and ask them to do it. By using this character type approach, we can get a depiction of someone’s personality and know what triggers them; their likes, dislikes, mindset, etc. Eventually, this will also helps us figure out the best way we can interact with them. 

However, when prematurely used to assess a stranger, or let’s say someone you have only met once, this method can become quite tricky and prone to inaccuracy. And I assume that this is the common case. When you’re trying to break the ice with someone, then it is most likely to be someone you haven’t known well. Hence, pitfall number one. Why do we fail to talk to this person? It is because we come with an assumption. When we are about to interact with someone we haven’t really known, the data that we have in our mind about this person are simply not enough to pull out a hypothesis. Simple research practices. Science people can back me up here. Going into a conversation without a ripe and justifiable assumption is like going into a battle with a blunt unsharpened sword. Therefore, ditch the assumption all together. Come with no preparation, to a certain extent. You don’t need it. Let the conversation steers itself, and not the assumption that you have already formed prior to the actual interaction. That way, you can focus your whole energy to really examine the person during the conversation and react accordingly. Treat the conversation as a discovery session where you are just simply trying to gain as much first-hand info about this person’s character. 

Moving on to the second common pitfall. Failure to decide how you want to represent yourself. We focus completely on pleasing the person in front of us so that we forget to decide an important question within ourselves. That question is: do you want people to see the real you, or do you want people to see what they want to see? The more you think about this, the more it becomes such a head scratcher. You will say, “Well, I need to be someone they want to see if I want to get along, right? But then I’m not being myself and it’s going to be exhausting to pretend. What happens if one day they see the real me and they don’t like it?” I hate to tell you this, but you can only pick one. If you choose to show your real self, you will definitely be burden-free but that will cause the result of your interaction to be unguaranteed. There is a good chance that you might only get along with people who are compatible with you. And probably not the opposite. What I have been doing in deciding which way to go, is to firstly determine whether I want the relationship with this person to be short-term or a long-term one? Based on the discovery that I did, can I see this person in my life for the next decade or so? If I meet someone at a party I’ve never thought I’d go to, there is a fair chance that the people I meet there won’t be making their way deep into my social circle. So, I will be more likely to take the short-term approach, unless I meet someone at the party who can be an exception. But, if I am in a situation where I am meeting some friends of a friend of mine – or mutual friends – I will choose to take the long-term approach and try to be my true self. If it doesn’t work for them, then so be it.

Once you have decided how you want to come off to the other person, you can then focus on how to master the conversation itself. But to do this, you need to be aware of the final pitfall. And that is: you may be saying too little, or saying too much. When we feel anxious and self-conscious, we tend to put our focus inwards rather than outwards. That is why, when finally faced with an awkward social situation, we go overboard and feel that we need to either calm down, or fill in every pause with words. Lucky for us, the key to eliminating this is pretty simple. Rather than focusing on yourself and what to say, focus on the other person. Forget the little details about yourself that are keeping your head occupied – how you look, how your expression is, or how your tone is – and instead shift it to the person you are talking to. Examine how they talk, their intonation when talking about something they are passionate about, or their expression when talking about something that they dislike. By doing this, you let the person know that you are interested in them. I believe that if the roles were reversed, you too would have noticed if the person you are talking to is interested in you or just themselves. And most importantly, doing this will also help you discover a lot more about the person on a much deeper level. And that can come in handy, should it turns out that you will have this person in your life for a long time down the road.

So, are you ready to break the ice and be the master of conversation? I would love to hear what you think! Shoot me an email at Or, connect with me through my website in, my Twitter in @lifeforexperts, or my Instagram in @lifeforexpert without the letter “s” at the end.

Thank you for trusting Life For Experts. Never stop learning to become an expert in life. I’m Dannis, and I will see you next time. Bye!


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