“You had that

masculine thing down:

Shoulders, back straight,

Never slumpin’,

never round.

It would turn me on

Just to see you walk

Into a room,

across the room,

Out of the room…

You really impressed me.”


— Jill Scott



“Men flourish in the gray area,” he says.

Don’t I know it, I think. Experience—and more than a few exes—has taught me well.

I’m perched at the counter of an upscale diner in Chicago, enjoying what may be the best pulled-pork sandwich I’ve ever had (and that bar is set pretty high). Both were the recommendation of my tall, dark-ish and very handsome brunch partner, who is demonstrating an unexpected candor, along with his great culinary taste.

I study him for a moment. It’s only our second meeting in person, after years as online acquaintances. Our first—only a few weeks before—had been fleeting, if a bit unsettling…

Wait. I should start at the beginning, shouldn’t I?

Truth is, I’d been aware of him for some time. An avid lover and occasional collector of fine art photography, I was excited to see someone advancing the visual conversations of greats like Gordon Parks and Roy DeCarava, both of whom I’d deeply admired.

But it’d only been a passing interest—passing through my news feed, that is—until I unexpectedly fell hard for one of his works. Strangely, it wasn’t one of the black-and-white portraits I generally gravitated towards, but a conceptual image: a red door against a blue sky on a barren desert landscape.

It was stark, and surrealist, and stunning. For days afterward, I couldn’t stop thinking about it. Intrigued, I finally felt compelled to inquire about buying it. Just a quick message in his inbox (though I suppose one could say I “slid into his DMs”)…

He responded within minutes. Alas, the object of my desire was far outside my current budget, but the inquiry initiated a brief but pleasant thread of communication—and a deeper interest in his work.

He explained that the image—one in an ongoing series—represented possibility.

Oh. I see.

So, when I discovered that my visit to our shared hometown coincided with his appearance at a local art show, it seemed only natural to stop by and say ‘hi’. You know, finally meet in person and show a little support…

Okay, so maybe I’d become interested in a little more than his work. And maybe, I was hoping to kill my swiftly growing curiosity. Truth was, it was becoming distracting—especially when my dating life had become so dull, as of late. There was absolutely no point in cultivating even a minor crush on a man in an entirely different time zone. Been there, done that, disaster.

Besides, no doubt the cute, charming and seemingly single lensman I’d suddenly become so aware of online would disappoint in person. It was inevitable. After all, if my now six-month-long crash course in online dating had taught me anything, it’s that our online presences are more often than not deceptive. Hell, most of us can’t even begin to live up to the personas we’ve so carefully curated for ourselves. (Me being the exception, of course. *wink*)

Yes. This was the thing to do: drop by for a quick meet-and-greet that’d snap everything right back into focus. Then, I’d go on my merry way—all the way back to New York, and my lackluster, but at least local dating life. Please and thank you. The end.

As my mother—another acquaintance of his—and I made our way through a labyrinth of vendors toward the booth where his work was displayed, I prayed: Be short. Like, way-shorter-than-me short. Like, tiny. (Note: I’m 5’10”. Height’s not a deal-breaker, but it is a factor.)

Speak in a ridiculous voice. Smell funny. Be obnoxious. Be inexcusably awkward. Be rude. Be repugnant.

I spotted him from several yards away, engrossed in conversation with a client he easily towered over. As we approached, I could hear the deep rumble of his voice and an irresistible South Side of Chicago drawl. He glanced up at us, sudden recognition coupled with a twinkle in his eye and a dazzling flash of teeth.


Damn, damn, DAMN!

He greeted me with an engulfing hug, and I was effectively disarmed—because I’m a sucker for a great hug. So much so, that I can’t recall what was said for the next five minutes or so that we lingered. It all became white noise, as I avoided making further eye contact by focusing on the incredible images adorning the walls…not the least of which was that red door.


This was a horrible idea. Everywhere I turned, I saw something I wanted. Including him.

Thankfully, we kept our visit blessedly short. Frankly, I’m not sure how much more time I could’ve spent staring everywhere but at him.

Okay, so that backfired

Good thing I was returning to New York, because, sweet Jesus: Tall, good-looking, intelligent and ridiculously talented? Even for a superwoman like me, this man was officially Kryptonite. And I had no doubt that he knew it.

So, I did exactly what one does when they find themselves irrationally attracted to a virtual stranger: I completely ignored it. I returned to the East Coast, to work and writing. I threw dinner parties, went to brunches, sipped cocktails and carried on with my usual routine…

Until he slid into my DMs, to tell me how great it’d been to meet me in person. How, oddly enough, when he’d hugged me it’d felt like he’d known me for years. How he’d love to get together sometime to chill and have a drink.


Damn, damn, damn.

And this is how, several weeks later and back in Chicago, I find myself sharing brunch with Mr. Gray Area, talking about art, the highs and lows of being career creatives, and about men, women, and the whole spectacular mess that is modern romance.

“Trust me, (men) will keep things ‘gray’ as long as we possibly can,” he says, chuckling.

“Yeah. No sh*t, Sherlock,” I counter with a smirk.

He chuckles again, before getting the check and leading me across the snowy street to a lounge at Soho House. We settle into a leather loveseat with our bourbons and banter, and it’s warm, and fun, and strangely familiar. And oddly, as attracted as I am to him, the air between us doesn’t feel heavy with desire. We’re just a woman and a man, tucked snugly away on a blustery Chicago afternoon, riffing on our respective lives. Harmlessly.

Maybe he isn’t Kryptonite, after all. Maybe he’s just a very likeable guy.

In fact, when he deposits me at my mother’s doorstep a few hours later, bidding me farewell with another of those fantastic—but friendly—hugs, I find myself wondering whether it’d even been a date. Gray area, indeed. But at the very least, I’ve made a new friend, which is a far more realistic scenario, anyway.

Once again, I fly back east the following day. It’ll be another couple of weeks before we communicate again, when he writes to congratulate me on an article I’ve had published.

This time, the exchanges continue—at first, sporadically, and then, in increasing and unexpected bursts that never fail to delight and entertain me. Over the weeks that follow, I become his de-facto fashion consultant, and he a welcome and hilarious distraction from a somewhat dark and difficult winter.

The ease with which we communicate is refreshing. We both have the habit of writing exactly as we speak, and therefore even our most mundane texts seem to have the same ease, cadence and humor as our conversations. And yet, I still can’t discern if we’re anything more than kindred spirits…

Until the day he casually mentions how “mesmerizing” I’d been in our brief afternoon together. And I’m so relieved, because I can now crush openly.

My reciprocity seems a relief to him as well, since our exchanges now become peppered with vague but potent innuendos and allusions to future meetings. While we make no definite plans, I become increasingly convinced that we should indeed meet again; sooner than later. Because he’s beginning to take up space he’s never physically occupied, and making it increasingly difficult for me to cultivate other…interests.

More importantly, I foresee us swiftly slipping into a gray area: Already, we are neither lovers, nor ‘just’ friends. And while he—by his own admission—is bound to flourish there, I know the gray area is well outside my comfort zone. I need to have a sense of my boundaries, and my bearings. The gray area is far too foggy for that.

And, whether it’d simply be to get it out of our systems, or actually explore some real possibility of one another, I frequently begin to wonder what it might be like if/when we see each other again, now that desire is most definitely in the air. It’s far too early to have any expectations—or even hopes—but the possibility is…intoxicating.

And it’s this possibility that has made its way into my dreams when the buzz of a text message awakens me late one recent morning. It’s Mr. Gray Area; greeting me with a picture of himself at an event the night before. I’d consulted on the suit.

We jump into our now-rhythmic repartee. As I’m still bleary eyed, I’m a bit slow on the take, despite the lateness of the hour. I reluctantly admit as much—and that I haven’t even risen from bed yet, having slept far later than usual.

“Hmm,” he replies.

I begin to protest that I’d been up until dawn, when he continues:

“Just had a thought of you rolling over towards me.”

The world seems to pause for a moment, before I realize it’s just my breath. Nothing gray about that—at all. I’m the writer; and yet, I think those ten words might comprise the most intimate, evocative and unexpectedly erotic sentence I’ve ever heard—or at least, that has ever been said to me. I have no idea if this is the first or fortieth time he’s said it, but once again, I have no doubt that he knows it.

Yeah, he definitely knows it.

Damn. Kryptonite.

About the author

Who me? I'm just your average Grammy-nominated goddess next door. May I borrow a cup of sugar? But seriously: I'm a musician, model, writer, all-around creative and devoted auntie. Like you, I'm just out here in the universe, trying to make it happen...whatever that is.