How do you strike up a real, genuine conversation?

Here’s one of those questions attributed to Alan Alda which I tucked away in my potential blog bank.

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As someone who regularly finds themselves in conversations with all manner of people – be they strangers or someone I already know – on all manner of subjects, there’s a general assumption that it’s easy for me, and that I’ll have all the answers to this question. And while I do have thoughts and observations, I’d like to preface them with saying, it’s not always easy. As a socially awkward teen, there were many utterly gruesome experiences and, although much of my adult life has seen a significant improvement, there’ve been periods in my life when those gruesome experiences have re-occurred.

These days I understand that my self-esteem and self-confidence are fragile, and when they are wobbly, social interaction can result in anything from simple awkwardness and discomfort, to an emotional battering leading to periods of self-imposed social isolation. I know this because I’ve been around the same group of people and been either shunned, or welcomed and thrived – the only difference being how I was feeling about myself. Like children and dogs (or sharks with blood in the water), people can pick up your vibe. One vibe is attractive, the other is most decidedly not.

It took me a while to work out that I don’t need to radiate confidence, just feeling secure is enough. And on that score, discovering how much impact having the wrong people in my life can have was a revelation, for there’s no doubt I’ve felt a great deal more secure without the input and influence of certain individuals.

So, assuming that a healthy degree of contentment in myself exists, here’s what I’ve observed are the next steps I take in order to have a real, genuine conversation.

With people who are new to me, obviously the basics of making eye contact, smiling and saying hello come first. Next the standard social chit-chat type of things while I observe the response and body language of the other person. If the person appears unwilling to engage, I leave it, but if their posture is open and they mirror me with the eye contact, smiling and social chit-chat, I ask an open question (one which requires more than a yes/no answer), then (and this is the important bit) I genuinely listen to the answer rather than simply wait for my turn to speak. If the conversation drifts onto a topic I know nothing of, instead of withdrawing politely or changing the subject, I ask them about it, as people love to share their enthusiasms and/or knowledge.

That’s the easy bit. It becomes trickier when there’ll likely be an ongoing relationship and it’s clear there’s significant differences. This is where I make the effort to find common ground. I start with the mindset that all the people in my life don’t need to share all my likes/dislikes, my political views, my principles and values, so long as shared aspects can be found. Let me offer you an example.

My new chiropractor is a fan of Charlie Kirk. I discovered this while still a new patient when the subject came up at the time of the fatal shooting. My immediate reaction was “oh no, how far am I going to have to travel to find someone else?” But instead of acting on that knee-jerk reaction, I engaged in calm and explorative conversations, and so discovered a significant range of topics where we are as one. We now get on so well, I’m one of only two patients who is aware his marriage has broken down and quite how heartsore he is about it. Simply speaking, we have demonstrated respect of and trust to one another, through the means of open and honest conversation, active listening, and humour.

I’m not suggesting there’s a need to have this type of conversation with everyone, and of course you cannot achieve this unless there is willingness and effort from both parties. I also hope I don’t need to say that when you can find nothing shared, feel free to step away and/or get those boundaries rapidly in place.

These are my thoughts on the subject, but what are your practices when meeting new people? Do you have techniques you use when you find yourself in an on-going relationship when your views don’t always align?

© Debs Carey, 2026