On a sunny Tuesday morning, somewhere between my third cup of coffee and the crush of Brooklyn commuters, a stranger hit me with a line so simple and profound, it all but rearranged the furniture in the living room of my mind. I still think about it—not just because it was clever, but because it reminded me that inspiration doesn’t always have to come from poetry or self-help books. Sometimes, it steps off the train in a wrinkled pinstripe suit and scuffed Oxfords.

The Elevator Incident

Let me set the scene: I was running late for an editorial meeting—big surprise—and darted into one of those old elevators with heavy, clunky doors that seem like they have all the time in the world. Inside stood a man, mid-40s, gray at the temples, who looked exhausted in a way only New York commuting can achieve. You’ve seen the type—a face like someone just told him the price of rent went up again.

As the elevator lurched and groaned past the first floor, he sighed, glanced my way, and said, “You’ll waste your youth sweating over the little things. It’s better to sweat over people who matter.”

I blinked. Was this man my subway-stranger-psychic? Did I exude an energy that screamed, This one’s been spiraling over a vague text for three hours?

The doors slid open before I could respond, and he was gone, leaving me with nothing but a cryptic nugget of unsolicited advice.

Why It Stuck

The thing is, he wasn’t wrong. As someone raised in a Nigerian household where achievement was practically a family heirloom, I’ve spent my life obsessing over the tiny, easily-ignored details. From what font to use on a high school essay to the best way to bring up “career goals” on a second date (spoiler alert: don’t overthink it), I’d perfected the art of sweating the small stuff.

And if you’ve ever dated—or tried to—there’s plenty of small stuff to sweat. Ghosting etiquette. Interpretive text dance-offs. Should your laugh in a group chat be a “lol” or a “😂”? I was always playing it safe, afraid of looking too eager or not eager enough. But this stranger’s offhand remark made me rethink the whole game.

Shift the Focus: People > Perfect Plans

If I’ve learned anything—both from my dating life and my parents’ 35-year partnership—it’s this: Connection trumps perfection, every single time. Of course, my mom always threw in an extra dash of “presentation matters,” too, but that’s neither here nor there.

The point is, the energy you spend agonizing over your quirks or future plans could be better spent learning about the person right in front of you. Ask yourself:

  • Are you getting to know who they actually are, or are you too focused on the version of them you’ve idealized in your head?
  • Are you trying to unlock their favorite conversation topics, or are you counting how long it’s been since you texted them back?
  • Most importantly, are you (gasp) ignoring how you feel in the process?

Vulnerability Is Sexy (Yes, Even If You're Awkward)

Here’s the thing: nobody’s expecting you to be perfectly smooth all the time. If there’s one thing I’ve learned from writing contemporary romance, it’s that awkward, messy moments often make for the most cinematic love stories. Trust me, I’ve stolen more inspiration for my characters from strangers fumbling on first dates than from Nicholas Sparks novel adaptations.

Case in point—back in college, I accidentally quoted a lyric from Fela Kuti while trying to impress someone, only to discover they thought I was referring to a Drake song. Mortifying? Sure, at first. But it became one of those funny little moments we laughed about several dates later, back when we still thought popcorn was a meal for two and “splitting utilities” was a far-off adult concept.

The moral of the story? People appreciate effort, even when it occasionally faceplants into awkwardness. What they don’t appreciate is someone holding back because they’re sweating the details.

Micro-Moments That Matter

Here’s something I took to heart after my brief encounter with Pinstripe Philosopher on that Tuesday morning. Often, the connections that feel the richest are built not on grand gestures, but on little micro-moments—grins exchanged over a terrible joke, the way someone remembers you hate celery without you having to tell them twice, or a perfectly-timed “thinking of you” text that hits on a random Wednesday afternoon.

The next time you feel compelled to overthink, breathe deep and focus on these small, meaningful ways to invest in someone instead of obsessing over their interpretation of your every move. A few ways I’ve tried it:

  1. Worry less about your next text and more about what they’ve already told you. Remembering details goes a long way.
  2. Lead with curiosity. Ever notice how asking, “Tell me more about that!” feels infinitely more attractive than, “What did you mean by that emoji?” Exactly.
  3. Normalize some level of uncertainty. Sometimes, you won’t know exactly where you stand with someone—and that’s okay. Connection grows in stages, like good Jollof rice. Don’t rush it.

Circle Back to What Matters

Fast-forward a few months from that stranger’s impromptu pep talk in the elevator. My editor didn’t kill me for being late that day (thank you, caffeine), and what started as harmless advice from a stranger turned into a mild obsession. I started mentally grading my interactions with new people based on whether I was focused on building a genuine connection—whether that meant my conversations were brimming with ridiculous tangent stories or simply sprinkled with quick, direct questions like, How’s your week going?

The results? Game-changing. I laughed more. Felt less stressed about getting it “right.” I even stopped trying to reverse-engineer dates to avoid looking awkward—because spoiler alert: everyone’s awkward sometimes.

Make Every Meeting Count

When I think back to that Tuesday morning, I still wonder if the stranger was dispensing life advice to everyone he met that day or if I just looked particularly frazzled. Either way, he was a reminder that random encounters often carry unexpected lessons. A passing stranger challenged me, in just a few words, to sweat less and love more.

And isn’t that kind of the whole point? Regardless of whether you’re starting something new, rekindling something old, or just trying to figure out what’s next, the question isn’t, “Did I get this perfectly right?” The question is, “Did I spend my energy on what matters?”

Because trust me: the elevator doors won’t always wait for you.