Stop Waiting for Deep Conversations to Happen (And Start Creating Them Instead)

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Here’s a confession that might sting a little.

Chris Burnett had been friends with some people since primary school. Decades of friendship. Countless memories together. And yet, when he sat down to actually interview them about their lives, he discovered he didn’t really know them at all.

“There’s still so much that I actually don’t know, or maybe thought I knew, but didn’t know quite the reality of it,” Chris told me on episode 56 of Friendship IRL.

Think about that for a minute. People he’d grown up with. Friends he’d spent years alongside. And he was still learning the fundamentals of who they were, what shaped them, and what mattered to them.

If that doesn’t make you question what you don’t actually know about your own people, I don’t know what will.

The Waiting Game We’re All Playing

Let’s get real about what’s actually happening here.

We’re all walking around assuming we know our friends and family because we’ve been in each other’s lives for years. We think depth will just… happen naturally. That one day we’ll magically find ourselves in those meaningful conversations we see in movies.

But here’s the truth: we’re all waiting for someone else to go first.

We’re waiting for the “right moment.” Waiting for them to open up. Waiting for some crisis or celebration to create the space for real talk. Waiting for permission to ask the questions we actually want to ask.

Meanwhile, our relationships stay exactly where they’ve always been. Comfortable, familiar, and honestly? Kind of surface-level.

Chris discovered this during the 2020 lockdowns when he felt disconnected and homesick (he’s Scottish, living in Australia at the time). After reading Tuesdays with Morrie, he decided to stop waiting and start creating the conversations he wanted to have.

What started as weekly catch-up calls turned into something extraordinary: 75 recorded interviews with his friends and family about their lives.

And here’s what he learned: the conversations we avoid having are exactly the ones that will transform our relationships.

Why We Keep Things Surface-Level

“I think interview is probably the word that people can kind of latch on to and understand,” Chris explained when I asked how he approached people about this project.

But here’s what I love about his approach: he wasn’t trying to become a professional interviewer. He was just a friend who decided to get curious about the people he cared about.

The problem is, we’ve convinced ourselves that going deeper requires some special skill or perfect timing. We think we need to wait for a crisis to ask real questions, or that casual friendships can’t handle vulnerable conversations.

We’ve made the connection way more complicated than it needs to be.

Chris proved that wrong by creating a simple three-part structure that anyone can use. No special training required. No perfect timing needed. Just intentional curiosity about the people you already care about.

The Three-Part Formula That Changes Everything

Here’s Chris’s framework, and honestly, it’s brilliant in its simplicity:

Part 1: Their Life Story

“Questions about their life. And that usually is the longest part. And it literally just goes through the chronology of child to school to career to what they’re up to at the minute.”

This isn’t rocket science. You’re asking: What were you like as a kid? What teachers or subjects stood out? What shaped who you became?

But here’s what Chris discovered: even with friends he’d known since childhood, there was still so much he didn’t actually know. Different teachers mattered to them. Different memories stood out. Their perspective on shared experiences was completely different from his.

“Some friends are quite adamant about turning the questions on to me when we talk,” Chris shared. Because once you show someone they matter enough for you to be genuinely curious about their story, they want to know yours too.

Part 2: Three Words

This part gave me actual chills. Chris asks each person to come prepared with three words they’d use to describe him, and he does the same for them. Then they share the words and explain why they chose them.

“It is a little awkward at first, especially with guys,” Chris admitted. “We just don’t really take the time to sit and actually say what we appreciate about one another.”

But here’s what happened: “Afterwards, they have been like, ‘You know what? That was great.’ It’s just a really nice thing to do.”

In the full episode, Chris goes much deeper into how this simple exercise opened doors in his male friendships that had never been opened before. The vulnerability, the appreciation, the permission to actually tell each other what they valued about their friendship. It changed everything.

One friend literally used “Scottish” as one of his three words, which sounds like a cop-out until Chris explained: “If somebody was like, ‘What do you mean Scottish?’ He would actually have an answer… most of our shared memories together have involved alcohol and I’ve got a really dry sarcastic sense of humor.”

It’s not about the perfect words. It’s about taking the time to really see each other.

Part 3: Memory Lane

“We took a trip down memory lane. So again, it’s a little bit of homework beforehand, I asked them to write down a few shared experiences, memories that come to mind when they think of us.”

This is where things get really fun. Chris discovered that what he considered insignificant moments were often the most meaningful memories for his friends. They’d remember completely different details from the same experiences.

“Part three could go on for an hour, an hour and a half, two hours easily,” Chris said about friends he’d known for years. “Your cheeks are sore from laughing.”

What Actually Happens When You Stop Waiting

Here’s the part that’s going to surprise you: this isn’t just about having one nice conversation and moving on.

“With people that I’d maybe lost a bit of touch with, doing the deeper dive recorded chat has brought us close together again,” Chris told me. “Quite a few friends have since returned to the ‘hey, it’s been a minute’ message to reach out.”

When you show someone they matter enough for you to be intentionally curious about their life, it removes their uncertainty about whether you actually care.

Think about it. How many friendships fade because we start doubting whether the other person still wants us in their life? How many family relationships stay surface-level because no one knows how to bridge the gap between small talk and real talk?

Chris’s project solved this by creating undeniable evidence that these relationships mattered to him. Not just “I’ve been thinking about you,” but “I’ve been thinking about you so much that I want to sit down and really understand your story.”

The complete episode explores how this played out in Chris’s family relationships, too. Sitting down one-on-one with aunts and uncles for the first time, learning things about cousins he’d somehow never known despite growing up together. His aunt was nervous beforehand because she didn’t feel “important enough” to be interviewed, but afterward said it was amazing.

Permission to Get Curious Right Now

Here’s what I want you to take away from this: you don’t need permission to get curious about the people you care about.

You don’t need a crisis to ask real questions. You don’t need to wait for them to go first. You don’t need special skills or perfect timing.

You just need to decide that the people in your life are worth knowing on a deeper level.

Chris wrote a book about this project because he wants just one person he doesn’t know to read it, try one conversation, and message him to say it mattered. That’s his goal… one person.

But I think he’s going to get a lot more than that. Because once you hear about this approach, it’s hard not to think about who you’d want to try it with.

Your Turn to Stop Waiting

So let me ask you this: Who in your life do you think you know, but maybe don’t really know?

Is it the friend you’ve had since college, but somehow never learned about their childhood? The family member you see at every holiday but never one-on-one? The person you used to be close with but have lost touch with over the years?

What if you stopped waiting for the perfect moment and just… asked?

What if you sent that “hey, it’s been a minute” text? What if you said, “I’ve been thinking about our friendship and I’d love to sit down and really catch up. Like, really catch up”?

I share so much more in the full episode about how Chris navigated the awkward parts, what happened when people opened up about difficult experiences, and why this project became his favorite hobby. His insights about creating space for vulnerability and the specific questions that led to the most meaningful conversations might give you exactly what you need to try this yourself.

Ready to stop waiting and start asking? [Listen to the complete episode here] and subscribe to Friendship IRL wherever you get your podcasts. Because the conversations that will change your relationships are the ones you create, not the ones you wait for.

And if Chris’s book inspires you to try even one interview with someone you care about, both he and I want to hear about it. The conversations we avoid having are exactly the ones that matter most.

Keep the conversation going.

Hi. I'm Alex.

I’m obsessed with helping people build the support systems they actually need. Through my book, podcast, and community, I share the frameworks that transformed my life from lonely and overwhelmed to deeply supported.

What’s your take? Let me know in the comments below.

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Hi. I'm Alex.

I believe everyone deserves a support system that actually holds them.

Friends to call after a rough day, emergency contacts, a neighbor who will grab your mail – I teach you how to create it all.

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