Why I always have a set of go-to icebreakers, and why you should too

As part of the preamble for a previous blog post, I mentioned my current go-to icebreaker. And, I thought it’d be cool to unpack why I do this.

It’s something I’ve done for a while now, since high-school days. It was definitely born out of a mild anxiety in social situations. So by having a set of seemingly random questions in my back pocket, I could always keep a conversation going.

Early days, when I was just a measly teenager figuring out my identity and place in the world, I’d honestly Google “questions to ask people to get know them better”. The original NYT article on ‘36 questions to fall in love’ came in clutch – not because I was trying to fall in love during these convos, but because these questions were a great model to initiate deep and thoughtful discussion. 

As I practiced this, there were questions I naturally gravitated toward and found myself re-using in different contexts, with different people. I can say in retrospect, that I probably leaned into these questions because they maximised response variance; i.e. you could tell a lot about a person depending on how they would respond.

These days, icebreakers have morphed into a form of market research. If there’s something I’m curious about, I can get a decent ‘lay of the land’ simply by asking an appropriate question.

So here’s a few questions I’ve used as icebreakers, with my answers too.

Q: "If you could change one thing right now, about yourself, about the world, about whatever, what would it be?"

A: First and foremost, have a think. I would urge the world to think with just a ‘lil bit more of an open mind and tiny bit more of an open heart <3. Oh and, fix your posture when you’re on your phone.

Q: "If you could ask an all knowing being one question, and get a definitive answer, what would it be?"

A: People I’ve asked this question to either:

• (a) have some entirely nice response, or
• (b) say something along the lines of:
  • 'am I on the correct path?'
  • ‘how can I be happier?’
  • ‘what would I be like if I made a different decision at point -x- in my life?’.

I live for the people who give type (a) answers because it always puts a smile on my face :)). And to the people who give type (b) answers I say, no one event can be classed as entirely good or bad – sometimes, things just happen. And as a certified nerd, I like to think of life as a test that you get to mark yourself. So why not give yourself 97/100 here and there?
Anyways, tangent aside, my response to this question is: if there was an even all-er knowing being, what would you ask it??

Q: “What’s something you are actively working on or working towards?”

A: This one is for me to know and for you, the reader, to find out ;)

PS. I was at a party recently where I was told: “You seem like someone who’d get along with all different kinds of people.” Besides being incredibly flattering, this person asked me a great question: “So how can you tell if you’re genuinely connecting with someone vs. just having a well performed chat?”.

For me, a genuine connection through conversation is hallmarked by flow.

When chatting with someone unfamiliar or new, I’m consciously tuned-in to a lot of cues – like tone, cadence, eye-contact, body language, and other subtleties, like outfit and jewellery. It’s a high-dimensional process, and as a conversation unfolds, I’m consciously piecing together appropriate responses. There are many layers of processing that underlie the art of the conversation.

However, when I’m speaking to someone familiar, or just someone I’m vibing with, there’s really not much on my mind. The high-dimensionality is stripped down and I feel free to respond with whatever comes to mind. I’m not too bothered about how my words will be received; I’m just flowing.