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What I Learned About Storytelling in Dating

author: lionel kalles finding stories life & everyday storytelling relationships & dating stories storytelling tips

The screen flashes a countdown: Round one begins in 3… 2… 1…

And then… nothing.

Just me, my webcam, and the echo of awkward silence.
My first date was a no-show.
Not exactly the start I imagined.

I signed up for a virtual speed dating event with local singles in my area.
Seven dates, seven minutes each.

The goal was simple. Meet people, make a connection, and maybe, just maybe, turn conversation into chemistry.

The night begins with doubt, regret and a small voice in my head saying maybe this was a bad idea.

I remind myself, “I’m here for the experiment”, and before I know it, round two begins…

 

Date #2: Finding the First Beat

Samantha appears on screen. She smiles, immediately leans in, and says,

“OMG! What’s behind you? Are those drums? Do you play?”

I laugh. “Yeah. I play. Not professionally, it’s kind of like therapy for me. Something that keeps me balanced”.

And there it was, the first real spark of connection.

We start talking about rhythm, creativity, and how we all need something that keeps us grounded.

We aren’t trying to impress each other; just sharing small truths that make us human.

Nearing the end, my cat (Ninja) decides to crash the date, jumping across the camera like he’s trying to keep me as a single cat dad. Luckily, she laughs.

I notice the timer ticking down, so I decide to ask my go-to question:

“When these seven minutes are up, what’s one thing you want me to remember about you?”

She thinks for a second and says, “I’m really good with my students, they’re special needs, so they need lots of attention. And I’m also pretty creative.”

A story comes to mind, and I nearly interrupt, but I catch myself. After all, this moment’s hers, not mine.

I realize that can’t be easy, and instead I say “Wow. Sounds like you’ve got a lot of patience.”

“Exactly,” she says, and I can tell she feels seen. Like I understood something she hadn’t quite named out loud.

The screen goes black, and before I know it, the first official virtual date is over.

I’d go on to learn my first lesson of the night.

Storytelling isn’t only about what I share — it’s about helping someone else uncover their own truth in the moment.

 

Date #3: Not so black and white

My next date, Serena, appears on screen with a blank white background and a black dress.
No bookshelf, no art, no distractions. Just her.

The conversation starts with a bit of small talk, the usual early dance of “where are you from” and “what do you do.” It feels a little empty and not particularly memorable.

So I went back to my anchor question:

“When these seven minutes are over, what do you want me to remember about you?”

She thinks for a moment. Then giggles.

“That I really love the colour pink. Like, everything I own is pink. My apartment, my dishes — even my personality, I’m very girly.”

I never would’ve guessed that, looking at her now, framed in black and white like a photograph hiding all its colour.

It was light, funny, and unexpected. and yet the answer told me everything.

Pink wasn’t just her favourite colour; it was her identity in disguise.

Serena would teach me that stories don’t always arrive as big revelations or emotional breakthroughs. Sometimes they’re hiding in the smallest details: the colour you choose, the things you collect, the parts of your life you don’t think twice about.

 

Date #4: The Detective

The next round begins with Betty.

“You’ve got a very professional setup,” she says, eyeing the drums and mic.
“Are you a podcaster… or maybe a musician?”

Laughing, I say. “A bit of both, actually.”

“I knew it!” she claims proudly.

That’s when she tells me she was basically Inspector Colombo — the old-school, trench-coat-wearing detective who notices everything and solves mysteries by paying attention to what everyone else misses.

We spend the next few minutes playing verbal ping-pong between curiosity, logic, and wonder.

I eventually share how I used to love mystery books as a kid — Encyclopedia Brown was my favorite— and that I’ve always been drawn to what makes people tick.
It was the most naturally flowing conversation of the night.

It reminds me that great stories are built on observation.

The more you notice, the more human things become.

And connection doesn’t come from grand gestures,. It comes from noticing what’s already there.

Date #5: Scheduled Break Time…

 

Date #6: Talking about our origins

By date six, I’m in rhythm, my nerves are gone, and I’m really enjoying the night.

Nina appears on screen with the warmest smile and for the first time, I feel a little spark of anticipation.
There’s a softness in her voice, an accent I can’t quite place

“Where are you from?”. I ask

“I grew up in the former Soviet Union,” she explains.

We start comparing notes on what it means to leave one place and start over somewhere else.

She talks about rebuilding her life, and eventually shares a story about learning to trust again. I can tell it wasn’t easy and share that with her.

I can hear the weight in her voice. There’s strength there, but also a kind of ache I recognize.

I tell her I know that feeling, that sometimes starting over means letting go of parts of yourself you didn’t even realize you were holding.

I notice there’s less than two minutes, and so I decide to take a risk and share something personal — the story about my red hair. How it got me teased as a kid, how I once punched a bully who called me “red-headed girl,” and how that moment taught me to stop hiding who I am.

As I talk, she leans in closer, her eyes fixated on me, smiling intensely.

And for a moment, the screen between us disappears, and I see vulnerability resonate in real-time.

I hadn’t just shared stories, I made a deep connection and a lasting impression.

My seven minutes with Nina would teach me that when you share honestly, you give people permission to do the same.

 

Date #7: Cats, Chaos, and Connection

The night ends with my final date — Rose — and, of course, Ninja, who can’t resist making another appearance.

“Is that your cat?” She laughs and smiles.

“Yeah — He’s been a third-wheel most of the night.” I explain, and instead of derailing the moment, it opens a door.

I tell her how I found Ninja and his sister, Samurai, on the street five years ago — how I couldn’t separate them, and how they’ve basically been my emotional support team ever since.

She nods, smiling, then tells me she’s been through a lot of change — leaving one career, figuring out what comes next, trying to rebuild trust in herself and in people.

I get it. I’ve started over, too. Left behind a whole different life to find something that actually feels like mine.

For the entire seven minutes, we managed to share stories about change, resilience, and finding new meaning in the middle of uncertainty.

I discovered the more real I am, the more real people become.

That vulnerability builds connection faster than charm ever could.

 

The Results

By the end of the night, I’d had five actual dates (one no-show and one break) — and two of them turned into matches.

For the analytical folks, that’s a 40% match rate, compared to the event average of about 12% (66% if you consider I was only interested in three out of the five dates).

Out of 618 participants, only about one in five walked away with a single match, and some didn’t connect with anyone at all.

So what changed the odds?

Not charm. Not rehearsed lines. Not luck.

Storytelling.

 

The Takeaway

Seven minutes at a time, I learned that storytelling isn’t just about being more memorable or entertaining.

Every time I shared a small story, they leaned in.
Every time I asked a real question, they opened up.
Every time I just showed up as myself, they did too.

A night of virtual speed dating would teach me that:
  • Patience creates space. When I listen, people open up.
  • Details reveal personality. Even a favourite colour can tell a story.
  • Observation builds trust. Paying attention is its own form of respect.
  • Honesty invites honesty. When I share my red-hair story, others share their own scars.
  • Vulnerability connects faster than charm. The more real I am, the more real people become.

And it turns out, storytelling works beautifully in the dating world — because what people want most isn’t a performance.

It’s honesty and genuine connection.

 


Author: Lionel Kalles
Storyteller · Coach · Marketing, Brand, & Sales Consultant


 

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