It was one of those sticky summer afternoons in D.C., the kind where you regret leaving the house the second you step outside. But there I was, standing in line for an iced coffee at a downtown café. Who needs cold drinks more than a guy trying to meet his deadline in 90-degree weather? The line snaked in slow motion—you’d think we were waiting for Beyoncé tickets, not caffeine. Behind me, a woman cleared her throat, leaning slightly to my right.

“Pretty hot today, huh?”

It was the kind of opener that could’ve gone either way—small talk or the prelude to something tangentially profound. I nodded and grunted an agreement. By my mental clock, I had about 20 seconds before I had to shuffle forward, order, and get back to pretending I was a productive member of society. But then she added something:

“You know, some people think small decisions don’t matter, but sometimes it’s the smallest thing—like choosing to wait in line—that leads to the best stories.”

Something in me had to pause. And not just because there was a double entendre about coffee brewing here.

The Unexpected Philosopher

She introduced herself as Ruby. Late 50s, silver-framed glasses, the kind of smile that made you wonder if she knew a secret the rest of us didn’t. We fell into easy conversation, her questions cutting past the usual D.C. “What do you do?” dance and landing somewhere more vulnerable.

“What do you care about?” she asked, after I mentioned that I was a writer.

I fumbled for an answer. Not because I didn’t know—it’s just that nobody ever led with that question. Most strangers at coffee shops keep it surface-level: the weather, traffic, maybe venturing into complaints about Metro delays if they’re feeling adventurous.

But Ruby wasn’t letting me off easy. An Amtrak train whistle in human form, she wanted to pry open different tracks.

“I guess… stories. Connecting with people,” I managed. That was safe, right? “What about you?”

She laughed and said, “Connection’s the same. But I also care about kindness. At this age, there’s nothing I want more—and nothing rarer than meeting someone who’s genuinely kind.”

There’s something about the way strangers can gut-check you. It’s like holding up a roadside mirror under the harsh glare of sunlight. Ruby didn’t say anything revolutionary, but her timing hit me like a long-overdue reminder—the kind of wisdom I’d heard from my Jamaican mother while she pulled double shifts, or from my dad over domino games. It’s the still, small truths that linger.

The Ice Bucket of Reflection

Later that night, I was running through the mental highlight reel of our conversation. Her words had seeded this itch in my brain: Am I being kind enough to the people in my life—friends, partners, even strangers?

Full transparency: Entering D.C. politics after undergrad doesn’t breed saintly habits. Navigating Georgetown’s hyperambitious culture meant I learned how to craft clever arguments, flex intellect like a weapon, and smooth-talk negotiations like a pro. But kindness? Backburner.

It made me think about past relationships: times I’d defaulted to being clever when I needed to be vulnerable, when I prioritized being right over being present. Maybe all those arguments over dinner didn’t need to escalate like HBO drama plotlines. Was I treating important people like busywork, expecting connection to survive on autopilot?

When Ruby told her own stories—about growing older, losing friends, and learning to let go of small grievances—she wasn’t aiming for Hallmark sentimentality. She knew the stakes. Her voice had that truth-serum quality, laughter flecked with gentle sadness.

“When you look back, Marcus,” she said as if we were already old friends, “you won’t regret being soft. You’ll only regret rushing past people who tried to show you their heart.”

Lessons From Ruby: Building Kindness Into Relationships

Ruby left me with food for thought (and no, not the overpriced muffin I considered but didn’t buy). If you’re reading this, wondering how any of this connects to your messy dating life, let me save you some time. Here’s the cliff-notes version of her wisdom:

  1. You Don’t Have to Be Flashy to Be Seen.
    Sometimes we’re so busy trying to impress people—crafting perfect first date outfits, curating Instagram-worthy vacation couples’ pics—that we fail to prioritize the small but meaningful ways to show someone we care. Ruby reminded me of the power in sincerely asking, How was your day—really?

  2. Kindness Costs Nothing, But It Changes Everything.
    Remember when we all thought giving the cold shoulder was cool? That performing emotional detachment was stealthily sexy? Yeah, no. Real connection happens when you’re bold enough to plant small seeds of compassion, even if it feels awkward or makes you vulnerable.

  3. Stay Curious.
    Ruby wasn’t afraid of diving deep—and that curiosity made her magnetic. Whether it’s in romance or friendship, people light up when they know you’re interested in them beyond surface-level polish.

  4. Apologize—and Mean It.
    One thing she mentioned in passing? The underrated magic of a genuine apology. Not the half-hearted “I guess I’m sorry you’re upset” non-apology but real ownership of your mistakes. Relationships aren’t about winning debates; they’re about repairing and recommitting without keeping score. Pair “I’m sorry” with “How can I fix this?” It’s a double-shot of healing energy.

  5. Let People Show You Who They Are.
    Ruby spoke about a former friend who tried to dominate every interaction, never pausing long enough to listen. It didn’t last. “Eventually,” she said, “people’s actions tell the story. Believe them the first time.”

Filling the Coffee Cup

The next time you find yourself in line—whether it’s a Starbucks queue, the DMV, or some metaphorical plateau in your love life—don’t ignore the Rubys around you. They’re walking reminders to slow the hustle and pay attention, not just with your eyes but with the softer parts of yourself.

Real love, real connection? It’s rooted in kindness. Not the grand gestures of rom-coms or viral Instagram posts, but the small, unglamorous, everyday choices. Like taking the time to ask what someone cares about—or even choosing the long coffee line just to see what story it serves up.

So take a page from Ruby’s book, and while you’re at it, add a little sweetness to your order. Life’s too short for bitter coffee—or shallow conversations.