The Habit That Saved Me

My love life could best be described as a series of near-misses, not unlike the Toronto Maple Leafs’ playoff runs—right there, so close, only to unravel spectacularly at the last minute. It wasn’t awful, but it wasn’t great either; somewhere between “How does this keep happening?” and “Maybe I’ll just adopt a cat.” However, about two years ago, I stumbled into a life-saving habit that changed the game—not just in dating, but in my overall approach to relationships. This singular habit sounds deceptively simple, but trust me, it’s like switching from dial-up to high-speed Wi-Fi. Ready? Here it is: I started actually listening.

I’ll explain. But first, let’s rewind.

“Sorry, What Did You Say?”

I used to think I was a good listener. I mean, I nodded thoughtfully during conversations. I offered advice when prompted (sometimes even when not prompted). I remembered one or two things people told me—birthdays, the occasional favorite Netflix series. But looking back, my approach to listening was about as deep as a puddle after summer rain. What I was doing wasn’t listening; it was waiting for my turn to talk.

This hit me during a date at a cozy sushi joint in Kensington Market. She was talking about her job—something to do with creating climate policies—but I was too focused on trying to come up with an impressive follow-up question to make her think I was “intellectually stimulating.” When she paused to sip her sake and looked at me expectantly, I froze. I’d heard words—climate, policies—but I couldn’t string them together in any meaningful way. My reply? A painful, vague “Wow, that must be so, uh, fulfilling.” Her response: polite smile, distant glance, check, please.

That night, I realized my mind had turned into a talk show panel, constantly preparing whatever clever line would secure the final rose. And while I was doing this, I was missing the actual person sitting across from me.

The Turning Point: From Listener to Learner

Changing this worn-out habit didn’t happen overnight. It started small—almost embarrassingly so. I resolved to shut up during conversations. Profound, I know. Like most habits, this one had to be intentional at first, requiring an embarrassing number of mental sticky notes to check myself. During a conversation, whenever my brain jumped six steps ahead (usually plotting how to flex some bit of trivia about 19th-century Canadian literature), I reminded myself to come back to the present.

To make things stick, I used this question as my compass: What can I learn from this person in front of me right now? Not in a job-interview, “What’s your biggest weakness?” way, but as an invitation to move past myself. Suddenly, listening wasn’t something I did passively; it became an active choice.

You wouldn’t believe what happened next—or actually, you probably would.

The Ripple Effects of Real Listening

This habit—the act of truly, actively listening—didn’t just help me avoid awkward silences on dates. It transformed every interaction I had, romantic or otherwise. Here’s why:

1. People Feel Seen (And That’s Magic)

Have you ever had someone light up simply because you remembered their niece’s name or asked for an update on their DIY refinishing project? It’s like offering someone a double-chocolate Timbit when they’ve only expected plain. Listening goes beyond words; it tells people, “You’re worth my attention.” In the dating world, this is like discovering cheat codes. People aren’t looking for perfect; they’re looking for present.

2. You’ll Hear What They Really Want

When you listen closely, people reveal themselves in ways no dating app bio ever could. An ex-girlfriend once casually mentioned she’d always wanted to try pottery. A few weeks later, we found ourselves elbow-deep in clay at a studio downtown. While the relationship didn’t last, her delighted reaction taught me to tune into the subtext. Listening isn’t just about hearing words; it’s about decoding what matters beneath them.

3. You Stop Overthinking Your Responses

When I stopped focusing on what I was going to say next, something wild happened: I started enjoying conversations. By leaning into curiosity instead of performance, I suddenly didn’t feel the need to “act smart” or “win points.” Conversations started flowing more naturally, like the jazz quartets I once saw in London pubs—imperfect, unpredictable, but infinitely better for it.

How You Can Build This Life-Saving Habit

Let’s translate my trial-and-error success into practical steps, shall we? Think of these as the relationship self-improvement plan you never knew you needed:

  1. Pause and Paraphrase
    Before responding to someone, habitually paraphrase what they just told you in your head. (Ex: “She feels stuck at work but loves the community garden she joined.”) This helps you process what’s been said and ensures you truly understand before replying.

  2. Ask Follow-Ups, Not Fixes
    Instead of offering advice—which, let’s be honest, often lands like spam emails—try asking follow-up questions. Example: If someone vents about their awful roommate, resist the urge to solve the problem. Instead, ask: “What would your dream living situation look like?” Listening is about connection, not problem-solving.

  3. Resist the Interruption Monster
    It’s tough, I know. Sometimes the perfect “me too” anecdote is on the tip of your tongue. But here’s the challenge: Let them finish. Hold back even when you’re dying to jump in. You can always share later.

  4. Put Away Distractions
    This one seems obvious, but it needs repeating until it sticks: Phones on silent. No checking for Leafs roster updates mid-conversation. Staying present starts with being physically there.

It’s Not All About You, But You’ll Change Too

Here’s the kicker: While attentive listening is a gift you give to others, it’s not a selfless act. In becoming a better listener, I started noticing changes in myself. The nervous chatter in my brain got quieter. I worried less about “being interesting” because I stopped putting that pressure on myself. “Hey, what are you about?” became the most fascinating question in my vocabulary—and the answers were gloriously varied. From a jazz singer dreaming of opening a café to a baker-turned-cartographer (long story), the stories I uncovered enriched my life in ways I couldn’t have predicted.

Even my friendships deepened. A buddy told me recently that he finally felt like I wasn’t just “hitting the mental snooze button” when we talked. Ouch, but fair. The habit spilled over into my writing too. My conversations gave me richer material—new voices, experiences, and perspectives to capture.

One Small Habit, One Giant Leap

Sometimes the smallest shifts cause the biggest waves. Learning to listen didn’t just “save” my love life—it dragged it out of the recycling bin, dusted it off, and rewired how I connect with people altogether. This habit taught me that attention is one of the rarest, most intimate gifts we can offer, and most people are dying for even a little of it.

So if you’re stuck on that romantic treadmill—cycling through meh connections and halfhearted coffee dates—my advice isn’t to learn pickup lines or rehearse date-night banter. It’s this: Close your mouth, open your ears, and see what happens. You might be surprised who sticks around to listen too.