How to start engaging in deep and difficult conversations?


Photo by kwanchaidp on DepositPhotos

This essay first appeared in This Singaporean Life (subscribe!), a newsletter I sent out every Sunday (SGT) where I share my weekly musings on work and life in Singapore.

When was the last time you had a heart-to-heart talk with people who matter to you? Or anyone for that matter?

I’m not sure if it’s the Singaporean culture or just our modern world, but deep and difficult conversations are becoming less commonplace, at least from my experience of living in Singapore all my life.

When we go deep into the painful and vulnerable depths of our hearts, it’s always unpleasant and uncomfortable.

Who enjoys talking about the unwanted break-up? How about the true reason why we’re not promoted? Let’s also not forget the failed attempt at joining the “cool” clique at school or work.

All these expose our shortcomings and most importantly, our weakest moments in our lives, to people who might judge, label, and even discriminate us.

But as much as we hate it, letting our guard down and talking about what makes us vulnerable and flawed as human beings are essential to engaging in deep and difficult conversations, which lead to more meaningful relationships.

So how do we start?

I wouldn’t rush to say I have a perfect answer but I’m going to share some insights into what worked for me personally, and hopefully, one or two would be useful to you.


First, I realised having one-on-one meetings with someone – anyone – whom you want to deepen the relationship with, is the first step.

And that means in-person meetings, by the way. Texting is not going to cut it, trust me.

Some may argue that it’s easier to open up over text. There are nuances at best and psychological barriers at worst, though.

It’s very different talking to an actual person while observing the subtleties of his or her posture, tone, and facial expressions, as compared to reading texts on a screen.

The emotional catharsis we experience when engaging in a conversation while sharing the same physical space can never be replicated by text conversations.

There’s a very good reason why people all over the world pay to attend live events – concerts, conferences, theatre plays, sports events, and the list goes on.


Talking about shameful events can remind ourselves of the pain we experienced. With a listening ear, though, we’re sharing the pain and letting that person into dark corners of our world.

That will either push that person away, which is better to happen earlier than later, or pull that person in.

Not everyone we meet is going to like us so why not know it sooner so we can give our time and attention to only those who matter?

Yes, it’s going to be akin to pulling the band-aid off a nasty wound. Isn’t that how the wound can truly heal, though? Even if a scar were to form, at least we know it’s not going to hurt anymore.

Everyone has scars, anyway, it’s just that some of us choose to conceal them and be ashamed quietly, while the rest decide to will the courage to show to those who are willing to accept our flaws.

The first step to acceptance of anything is acknowledging its presence. It’s going to be tough, but knowing there’s someone else by our side is comforting, to say the least.


Now for the most important piece of the puzzle based on personal experience: listening.

Everything mentioned above was about ourselves, investing the time for one-on-one in-person meetings, and being vulnerable and talking about what hurts us to let them in.

However, if we only focus on ourselves, there’ll be no engagement and thus, no forging of a meaningful relationship.

Alright, I know. You might be thinking, “Why is this writer sharing something so rudimentary? Everyone knows listening is important”.

How many of us know how to listen, though? It’s not simply nodding your head, repeating what the other person is saying, or even maintaining eye contact.

It’s taking what he or she is saying, internalising it, and asking yourself, “What would I do if that happened to me?” Yes, it’s empathy. We all know what it means, but find it so hard to practise.

Empathy is a tough topic to tackle, so I’ll leave it for another essay to address. But to not leave you hanging, there one main thing I try my best to do: Ask enough questions to better understand the root causes of the other person’s problems.

Root causes lead to the underlying emotions of what the person is feeling, and are their band-aids to the dark corners of their lives.

Call to action

Challenge yourself if you’re more of a text person. Meet the people whom you want to build relationships with, one-to-one and in person. Even if you’re not a text person, invest more time in in-person meetings.

Spill your guts out, metaphorically, let them know what hurt you in the past. Listen, understand, and offer help. The other person will do the same if he or she looks at you the same way as you do.

Let’s engage in deep and difficult conversations with the people who matter the most to us.

“The only way to have a friend is to be one.” – Ralph Waldo Emerson

About the author

Vance Wong

Brain-picker. Cinephile. Koreaboo.

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by Vance Wong


Vance Wong

Brain-picker. Cinephile. Koreaboo.