5 Unexpected Ways to Go Beyond Small Talk and Build Deep Connections
If your friendships feel shallow, you’re probably making these mistakes
I used to believe deep conversations just happened. If you come across the right people, the ones meant to be in your orbit, words would spill out naturally and instant connection.
Yeah, no.
What actually goes down? You sip your drink, nod at predictable chit-chat, and replay the same tired script for the millionth time. How’s work? Crazy weather, huh? How ‘bout that traffic? Meanwhile, part of your brain is throwing furniture, screaming, Please, for the love of all things holy, let’s talk about something real.
Well, turns out, if you want that? You gotta make it happen.
Here’s how.
Ask Questions That Don’t Suck
Most conversations are doomed from the jump. Why? Because people ask questions that make talking feel like a chore.
"How’s work?" gets you "Busy."
"What do you do?" gets you "Uh, marketing."
Dead ends. Nothing to latch onto.
Instead, throw out questions that force people to think—questions that feel like flipping a switch in their brain.
"What’s something you’ve been obsessing over lately?"
"If you had an extra hour in your day, how would you actually use it?"
"What’s a totally useless skill you’re weirdly proud of?"
People wake up when they’re asked something they haven’t already answered five hundred times this week.
Let Silence Do Some of the Work
You ever see two people who are close? They sit in silence like it’s no big deal. That’s the kind of thing you gotta start getting comfortable with.
Most people panic the second a pause hits. They scramble to fill it with whatever nonsense spills out of their mouth. That’s how you wind up talking about the price of avocados at Costco for twenty minutes.
Instead? Pause longer than feels normal.
Ask a good question, then zip it. Give the silence a beat longer than your instincts tell you to. People will fill it, and most of the time, they’ll finally say something real instead of just reacting on autopilot.
Yeah, it feels awkward at first. Like you’ve forgotten how to function. But once you get it, You’ll notice how much better conversations get when you stop rushing to fill every space.
Drop the Fake and Share Something Real
Have you ever been in a chat where both of you are waiting for the other person to get real first? So you just hover in this weird, polite limbo, talking about nothing?
Fix that. Go first.
Skip the default "Yeah, I’m good." and try "Honestly? This week has been kind of a mess. I’ve been feeling stuck." Then watch what happens.
People mirror the energy you bring. You keep it surface-level, they do too. You let something genuine slip out, and suddenly, they’re following your lead.
This doesn’t mean unloading your deepest traumas on some poor stranger. Just lead with something human.
For example:
"I’ve been thinking a lot about how much people change over time. Ever feel like you’re an entirely different person than you were five years ago?"
4. Build Shared Stories Instead of Just Talking
Deep friendships don’t come from a never-ending game of Let’s Talk About Our Feelings. They come from doing things together—from shared stories, inside jokes, and ridiculous moments you can look back on.
Road trips? Why do they bond people so fast? Because unexpected stuff happens, stupid jokes are born, and, you have history.
Start doing things instead of just talking.
Drag someone into something out of the ordinary. Doesn’t have to be huge—just different enough to break the script.
Work on literally anything together. A project, a dumb idea, a weekend plan. Collaboration breeds connection.
If every interaction you have revolves around coffee and surface talk, you’re missing one of the fastest ways to make real friendships stick.
5. Say the Thing Everyone’s Thinking
Some of the best conversations start when someone finally says what’s been hovering in the air.
"I feel like we always talk about work, but I don’t actually know what excites you. What’s something that makes you light up?"
"We’ve known each other for a while, but I don’t think I’ve ever asked—what’s one of the biggest turning points in your life?"
"Okay, I suck at small talk. Can we just get straight into the non fake stuff instead?"
People want depth. They’re just waiting for someone to give them permission. Might as well be you.
Try one of these today. See what happens.
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