Yes, I’m flirting with you.

On hand-written notes, the seduction of certainty, and finding pleasure in discomfort

I’d never been asked out in person before this year, but suddenly it’s happening all the time.

That alone would be enough to warrant commentary. But it’s the format, not just the content, which has surprised me most.

Over the past couple of months, multiple people have delivered me hand-written notes asking me out.

In the quiet room of my co-working space, I left my laptop to grab some water and came back to a folded note on my desk. I glanced around at the two men working quietly at the shared table, and opened the note. You have great energy, it said, would you want to go to dinner with me? The note was unsigned. I looked up again. The guy across from me was grinning.

Once was a fluke. But then it happened a second time.

I sat wedged near a potted plant, hunched over my laptop. Someone I’d chatted with briefly earlier that day walked past my desk and handed me a folded note. “This is for you,” he said with a smile, and kept walking. I noticed a fun energy between us, the note said, want to grab coffee sometime?

Reader: I loved it. It felt like Valentine’s Day in elementary school! It felt like middle school, if I’d ever been asked out back then! (I mean, I told them both no. But still.)

This note-passing phenomenon became a parody of itself. My favorite was when a crush heard about the trend and surprised me with a bundle of cookies, along with her own hand-written note, simultaneously out-doing and roasting the poor guys I’d turned down.

Mostly, I was delighted to discover I was unknowingly radiating this new, magnetic energy. I’ve always considered myself to be very bad at flirting.

flirting definitely involves hair-twirling, I know that much

**

In the past, I’ve been told I come off as unapproachable. The word “intimidating” got thrown around a lot. Maybe as a nicer way of saying frigid, robotic, and/or off-putting?

I always envied my flirty friends and the easy way they charmed people. I wrote about this in detail in the Nashville Scene’s Love issue, in an essay about my ill-fated, post-divorce dating spree:

I'd been studying the mechanics of flirting. In high school, I’d watched my best friend do it effortlessly: a hair flip, lingering eye contact, a casual knee touch. It came instinctually to her, but I felt like Jane Goodall observing a strange creature's behavior in the wild. Telegraphing my desire in that way felt unthinkably vulnerable.

That last line—the strong aversion to vulnerability—was the real issue.

Flirting activated my key fears: being seen in any capacity, wanting something I might not get, interacting with strangers who would probably hate me. But primarily, a deep-rooted fear of uncertainty.

I’m a Type A, Enneagram 3, Gifted & Talented™️ oldest sister. I wasn’t one for taking risks. My entire life has been orchestrated around knowing the expectations for success and performing exactly that.

That approach didn’t work with flirting. It couldn’t be studied, planned, or prepared for. Flirting is an exercise in improv: fluid, unscripted, and completely unpredictable.

Fundamentally, flirting requires comfort with uncertainty.

Historically, I’ve done everything possible to avoid that.

**

For me, these past two years have been a crash course in getting comfortable with risk and uncertainty.

If you’re new here (perhaps because I offered to French kiss my thousandth subscriber) a quick recap: In 2022, I sold all my things, went leaseless, and bought a one-way ticket out of the country. I’ve traveled solo, lived abroad and roadtripped across the US. I’ve been living out of a suitcase ever since.

When I first considered taking that leap, I was terrified. There was a not-small part of me still desperate to stay on the clear, paved path where things felt safe and certain. It was boring, yes, and even suffocating at times. But I always knew what to expect.

Certainty is seductive. It tempts us with the idea that if we just follow the correct steps, we’ll get a guaranteed outcome. That’s what religion promised. That’s what the default path (college-career-marriage-mortgage-retirement) promised. Hell, that’s what dating apps promise! A frictionless experience that eliminates the need to sit in the messy, horrible complexity of not-knowing.

In her fantastic essay, “The death of sex,”

Haley Nahman

explains how “sexlessness” — the absence of risk, friction, and discomfort in our over-optimized modern lives— robs us of real pleasure.

I’ve started thinking of this quality as sexlessness. I’m using sex here as a euphemism for the natural arousal that attends life in 3D, sexual or not. […] The techy pursuit of immediacy and frictionlessness which have become hallmarks of modern progress are comically at odds with genuine pleasure. Here my use of sex becomes more literal: Imagine it without friction.

For the illusion of certainty — because it’s always just an illusion, isn’t it? — we are too willing to give up all kinds of good things.

We miss out on the sticky, strange, gloriously awkward tension of real-life encounters. We take the well-trodden path rather than charting a course for ourselves. We deny ourselves the experience of facing the unknown and coming out alive, enlivened. We never get to meet the person that risk turns us into, and all the new things it makes us capable of.

Despite its allure, certainty had never really served me. My aversion to risk and discomfort had only ever made my life smaller and less interesting.

Real pleasure—real transformation—requires friction.

**

On that very first trip in 2022, I eased into uncertainty. I treated it as an experiment. Discomfort could not be avoided, so I would choose new discomfort: the option that felt unconventional, surprising, or slightly risky. Growth lives on the edge of the familiar.

From The Artist’s Way:

“There is something enlivening about expanding our self-definition, and a risk does exactly that. Selecting a challenge and meeting it creates a sense of self-empowerment that becomes the ground for further successful challenges.

That first risk spawned many more. I stopped drinking, got strong, and talked to strangers. I released old beliefs, retired default societal scripts, and created my own blueprint for a fulfilling life. I started writing my first book.

What have these last two years been if not a whole-hearted, full-send attempt to put myself into new situations, expose myself to the unknown, and trust that I will be transformed by it?

Perhaps nowhere was this more clear to me than in my creative practice. When we don’t know, we get to find out. We engage with the world from a place of attentiveness and curiosity. We embrace a sense of exploration and play, asking “What would happen if…? We hold things loosely. We’re receptive and fluid, ready for whatever reveals itself.

Uncertainty keeps us awake to possibility.

Honestly, isn’t that exactly what flirting is?

**

I haven’t stopped thinking about this line from

Sherry Ning

since I read it:

“Flirting turns uncertainty, something we usually fear, into pleasure.”

All the best things in my life have emerged from risk and discomfort. Uncertainty isn’t something to be avoided. Uncertainty is a portal.

Now that I’ve experienced its transformative power, I’m not just tolerating it—I’m chasing it. And it has turned me into a shameless flirt.

To be clear, this isn’t just about romance. Alain de Botton describes flirting as “the attempt to awaken somebody else to their attractiveness” through showing genuine interest, and adding playfulness and warmth to any human interaction. By this definition, flirting is not a means, but an end in itself.

I’ve come to see flirting as a spiritual practice. It’s a way of engaging with risk, uncertainty, and possibility—and inviting others to do the same. It’s how I want to approach life: Existing in a constant state of play, exploration, attentiveness, and curiosity. Open to whatever unfolds. Awake to possibility.

**

Now that I’ve flipped on the flirting switch, there’s no turning it off.

There’s chemistry between me and everyone now. The mailman. The old couple at the post office. The grocery store clerk. Every single person at my co-working space. It’s obscene. I can’t stop. And I don’t want to!

I have no intention of dialing it back. In fact, I want more. More banter, more office kitchen compliments, more hand-written notes.* If a few loverboys get caught in the crosshairs, so be it. 😏

Love,

Lane 💋

*DM for my mailing address.