3 Quick Tips To Become 10x More Interesting In Conversation

Stephen Hussey

In a recent commencement speech the New York Times columnist David Brooks said: “Marriage is a 50-year conversation”. In our search for a life partner he then asks us to reflect on the question: “Have I met someone I can talk to for that length of time?”

I love this quote because it underscores one of my beliefs that relationships are largely about finding someone we can be constantly curious about, someone who makes us always want to explore their mind further and who stimulates our brain in just the right way.

But how do we become that person for someone else?


Part of relationships come down to natural chemistry,  but they also come down to how much we work on our communication and conversation skills so that we know how to bring our best to the table.

So here are 3 quick things I’ve learnt about making great conversation:

1. Ask better questions

Quality questions make you more interesting than nearly anything else.

People love being able to talk about their views and opinions, and the more you give them permission to do it, the more they’ll look forward to conversations with you.

For example, you’re both on a date in an art gallery. You could say: “What’s the most moving piece of art you’ve ever seen?”, or if that sounds too conceptual, say: “What kind of art would you fill your ideal room with?”

On a more personal level, you can ask someone about their history, e.g. “When did you first realise you loved being a teacher?” , “What made you decide to move to another country?” People love talking about how they got to where they are now (as well as where they’d like to go), so don’t be afraid to dig into their past and future.

2. Read more

Great conversation is essentially two minds interacting, so it’s important to keep your brain fed with interesting thoughts to share. 

There are no shortcuts or “hacks” for this: the best advice is simply to read and learn more. Articles, books, blogs, podcasts (if you’re being lazy) – anything that gives you meat to chew on and something fascinating to add on a given topic.

Although you never want to show off you’re learning (it should always be revealed gradually), you can usually find ways to weave it into conversation: e.g. “I found the most incredible theory about relationships today”, or “I read this amazing article about the work habits of film directors”.

If it sounds strange to bring it up, you can just say: “I thought you’d find this interesting…” and then launch into what you read. Usually the person will be flattered you thought of them.

3. Show “confident vulnerability”

When you give more in conversation, you get more back.

The author Brené Brown writes: “Staying vulnerable is a risk we have to take if we want to experience connection.”

People often mistake vulnerability for spilling out all their sadness and worst experiences. They assume that it means letting out their weakest sides. But that need not be the case. 

What we need is a confident vulnerability: this means checking our ego at the door, being willing to drop our guard and be real. Vulnerability is about sharing that story that makes you look less-than-perfect. It’s just being comfortable with your authentic reaction, or giving someone else comfort, or being ok with your dorky side.

The more authentic your emotions are the more someone will feel connected to you, instead of feeling like they’re talking to a mask you wear in public.

* * *
There are so many elements to great conversation that I can’t go into them all here, but I hope these give you a good place to get started. If you want more, make sure to check out my post on how to have deep conversations with a guy.

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