I dated a lot, but I never really had anyone who was worthy of an

Host: The night had settled over the city like a slow exhale, pressing against the windows with the soft hum of distant sirens and the rhythmic flicker of neon. The bar was nearly empty—just the low throb of jazz from a forgotten speaker, the smell of citrus, alcohol, and lonely laughter hanging in the air.

Jack sat in a corner booth, sleeves rolled up, his grey eyes dull but steady. His glass was half-full of something that looked like amber regret. Across from him, Jeeny sipped water through a straw, tracing a slow circle on the rim of the glass.

On the napkin between them, scrawled in his rough handwriting, were the words she’d made him write down earlier that evening:
“I dated a lot, but I never really had anyone who was worthy of an anniversary. And most girlfriends never made it to a year, anyway.” — Wale.

She looked at the napkin, then at him, and smiled—not mockingly, but with that quiet, surgical empathy she carried like a blade.

Jeeny: “That’s a confession disguised as bravado, Jack. You sound like you’re proud of being untouchable.”

Jack: (smirking) “Untouchable? No. Just realistic. Some people are built for forever. I’m built for the moment. Why pretend otherwise?”

Host: The bartender wiped down the counter in slow, hypnotic strokes. Outside, a streetlight flickered, throwing quicksilver shadows across the wet pavement.

Jeeny: “You mean you’re built for escape. You think cutting things off early saves you from pain, but it just leaves you numb. You can’t build a home in a series of hotel rooms.”

Jack: “Homes burn down. Hotel rooms don’t.”

Jeeny: “You say that like temporary is safer than empty.”

Host: The air between them tightened, full of the kind of silence that tastes like truth. Jack leaned back, his voice low, sardonic, but soft around the edges—as if mocking himself more than her.

Jack: “You know what happens when you give someone a year? They start expecting a next one. Expectations turn love into obligation. I’d rather be honest from the start.”

Jeeny: “Honesty without vulnerability is just self-defense, Jack. You call it truth, but it’s just fear in a leather jacket.”

Jack: “Maybe. But at least I don’t lie about it. Wale had it right—some people just aren’t anniversary material.”

Jeeny: “No one starts as anniversary material. You become it. You earn it. Love’s not a trophy you find—it’s a rhythm you keep when everything else starts to sound off-beat.”

Host: The light from the hanging lamp above them caught in Jeeny’s eyes, turning brown to bronze. She leaned forward slightly, her voice lowering to a whisper.

Jeeny: “You ever wonder if the problem isn’t that they weren’t worthy, but that you never stayed long enough to find out?”

Jack: “Maybe. Or maybe I knew early. Maybe it’s better to walk away than drag something past its expiration date.”

Jeeny: “Love isn’t milk, Jack. It doesn’t go bad—it changes. You can’t judge connection on how smooth the beginning feels.”

Host: He looked away then, toward the bar mirror. His reflection stared back, warped by the glass—older, distant, the kind of man who built walls out of charm.

Jack: “You sound like you’ve never had your heart kicked in.”

Jeeny: “No, I have. But I didn’t build a fortress. I built a garden. Some things die there—but others grow back.”

Host: A soft song started on the jukebox—an old soul track, the kind that makes the air feel heavy with someone else’s memory. Jack’s fingers tapped unconsciously against the table.

Jack: “You think people like me can change?”

Jeeny: “I think people like you want to. You just hide behind cynicism because it feels safer than hope.”

Jack: “Hope’s for fools.”

Jeeny: “Then maybe that’s what it takes to fall in love—being foolish enough to think this time could be different.”

Host: He laughed quietly, the sound sharp but tired, like glass clinking against ice. He took a long drink, eyes on the window where rain had begun to trace crooked paths down the glass.

Jack: “You ever notice how everyone talks about love like it’s a destination? Nobody talks about how much maintenance it takes just to stay there.”

Jeeny: “Maybe because the best parts of love don’t happen in the grand moments. They happen in the ordinary—in the mornings when you don’t feel like talking, or the nights when silence says enough.”

Jack: “You really believe that? After everything?”

Jeeny: “I do. Because I’ve seen people stay even when it stopped being easy. You call that foolish—I call it sacred.”

Host: The rain thickened, drumming softly against the window, each drop like a ticking clock. Jack looked down at the napkin again, at the quote he’d written in a moment of careless honesty.

Jack: “You know, when I wrote that, I thought it sounded cool. Detached. But now it just sounds... lonely.”

Jeeny: “It is lonely. But admitting that’s the first thing that makes you less so.”

Jack: “So what—just keep trying until someone decides I’m worth a calendar date?”

Jeeny: “No. Keep trying until you decide you are.”

Host: The words hung there, soft and immovable. The neon sign outside flickered, reflecting against Jack’s face, splitting his expression into two—half shadow, half light.

Jack: “You make it sound so simple.”

Jeeny: “It’s not. But simplicity isn’t the same as ease. Love isn’t a victory, Jack—it’s a practice.”

Jack: “And what if I’m out of practice?”

Jeeny: “Then start small. Remember someone’s favorite song. Text first. Show up. Stay through the quiet. It’s not about a year—it’s about being present long enough to matter.”

Host: The music faded, replaced by the soft buzz of the city outside. Jack leaned back, exhaling, a faint smile tugging at the corner of his mouth—the kind that hides an ache behind humor.

Jack: “You’d make a terrible cynic, you know that?”

Jeeny: “That’s why I keep you around.”

Host: Their laughter rippled through the empty bar, gentle and tired but alive. Outside, the rain slowed to a drizzle, leaving the streets slick and gleaming under the soft glow of streetlights.

Jack reached for the napkin, folded it carefully, and slipped it into his pocket.

Jack: “Maybe next year, I’ll have someone to argue about this with.”

Jeeny: “Or maybe you’ll realize you already do.”

Host: For a long moment, neither of them spoke. The city exhaled. The air smelled of wet pavement and small beginnings.

And as the last note of jazz faded, Jack looked at Jeeny—not the way one looks at a friend, but the way someone looks at something they’re almost ready to believe in.

Because somewhere between bravado and vulnerability, between detachment and desire, he finally understood—

that anniversaries aren’t counted in years,
but in the moments when you finally stop running
and decide to stay.