I think you create your own hipness.

Host: The neon hum of the downtown diner bled through the half-open blinds, painting the walls with slow-moving stripes of pink and blue. It was late — that fragile hour when the night has gone quiet but hasn’t yet surrendered to morning. Vinyl booths glistened beneath dim light, and the air carried the mingled scents of coffee, cigarettes, and the faint echo of old soul music leaking from a jukebox in the corner.

Host: Jack sat at the counter, spinning a spoon in his half-empty cup, his reflection distorted in the metal surface. Jeeny slid into the stool beside him, her hair loose, her eyes alive, a smirk curling like a lyric.

Jeeny: (playfully) “Peabo Bryson once said, ‘I think you create your own hipness.’”
(She glances at him.) “So tell me, Jack — do you think you’re hip?”

Jack: (deadpan) “Hip? No. I’m too tired for that. Hip takes energy. It’s for people who still think cool means something.”

Jeeny: “Cool always means something. Even when it doesn’t.”

Jack: “That sounds like a line from a bad jazz song.”

Jeeny: “Or a good one.”

Host: The jukebox clicked, changing tracks. Marvin Gaye now — “Trouble Man.” The bassline rolled through the diner like smoke, soft and confident.

Jack: “You really believe that? That people can make their own hipness?”

Jeeny: “Absolutely. Hipness isn’t a trend; it’s a state of mind. It’s the art of being unapologetically yourself — even when nobody claps for it.”

Jack: (sipping his coffee) “So, what, it’s confidence?”

Jeeny: “Not confidence. Authenticity. There’s a difference. Confidence is loud. Authenticity hums.”

Host: The rain began, tapping gently on the windows, the drops catching the neon glow like liquid rhythm. Outside, the street reflected the lights of passing cars, rippling in puddles like melted color.

Jack: “You make it sound poetic. But the world runs on image, Jeeny. You can ‘create your own hipness’ all you want — but if no one’s watching, does it even exist?”

Jeeny: “It exists the moment you stop needing to be seen. That’s the paradox, Jack. The truly hip don’t chase relevance — they radiate it.”

Jack: “So, hipness is radiation now?”

Jeeny: “Exactly. A quiet glow. It doesn’t announce itself. It infects the room.”

Host: Jack chuckled — that low, rare sound that broke the weight of his cynicism for just a moment.

Jack: “You know, when I was younger, I used to chase that — the feeling of being cool. Every bar, every band, every crowd. It was like oxygen. Then one day, I woke up and realized… nobody remembers who was hip ten years ago.”

Jeeny: “And yet, here we are, still quoting Peabo Bryson.”

Jack: (grinning) “Touché.”

Host: The waitress, an older woman with tired eyes and red lipstick, refilled their cups without asking. She smiled faintly before walking away, her steps syncing to the rhythm of the music.

Jeeny: “You know what I think he meant? That hipness isn’t external at all. It’s alignment. When who you are, what you love, and how you move all finally agree.”

Jack: “That’s a pretty definition.”

Jeeny: “Pretty and true.”

Host: The lights flickered, as if in agreement. Jeeny leaned forward, her chin resting on her hand.

Jeeny: “Think about it. Miles Davis. Prince. Nina Simone. None of them were chasing fashion — they were the fashion. They didn’t care if you got it. They created worlds where you had to catch up.”

Jack: “You’re talking about icons.”

Jeeny: “No. I’m talking about conviction. That’s the real currency of cool.”

Host: Jack looked out the window — a man in a trench coat hurried through the rain, his shadow stretching across the slick pavement. The city glowed like a living thing — flawed, alive, and utterly unbothered by who was watching.

Jack: “You know, I miss that. People having edges. Everything’s so curated now — even rebellion comes with filters.”

Jeeny: “That’s why real hipness is rare. It’s not about rebellion anymore. It’s about resistance. Quiet resistance. To imitation, to performance, to fear.”

Jack: (nodding slowly) “So being hip means being brave enough to be boring.”

Jeeny: (laughing) “Exactly! The courage to not care who’s ranking you. The grace to look ordinary while living extraordinary.”

Host: The rain intensified — not angry, just honest. The sound filled the empty spaces in their conversation.

Jack: “You ever wonder if people like Peabo Bryson ever worried about that? About staying relevant?”

Jeeny: “Maybe. But he was smart enough to realize that relevance isn’t about staying trendy — it’s about staying true.”

Jack: “You sound like a lyricist tonight.”

Jeeny: “Maybe I’m just listening right.”

Host: The music faded, replaced by the faint whir of the coffee machine shutting down. The clock on the wall struck midnight — that soft, uncertain time when even the city seems to breathe slower.

Jack: (after a pause) “You know what’s funny? The older I get, the less I want to impress anyone. I just want to mean what I do.”

Jeeny: “That’s it, Jack. That’s hipness. Right there. Doing what you do because it feels like you.”

Jack: (smiling faintly) “So, authenticity is the new rebellion.”

Jeeny: “Always has been. We just keep forgetting it.”

Host: The waitress turned off the neon sign by the door — “Open” flickered once, twice, then died, leaving only the soft glow of the streetlights outside.

Jeeny: “You know what I think, Jack?”

Jack: “What’s that?”

Jeeny: “I think every time someone stops chasing approval, the world gets a little cooler.”

Jack: “You think the world notices?”

Jeeny: “No. But maybe it doesn’t have to.”

Host: He looked at her — really looked — and for once, there was no irony in his eyes. Just calm.

Jack: “Maybe hipness is just honesty with better rhythm.”

Jeeny: (grinning) “And you’ve finally got both.”

Host: Outside, the rain began to ease. The street shimmered like glass. Somewhere down the block, a saxophone player began to play under an awning — slow, soulful, unapologetically his own.

Host: They sat in silence, listening — not to the notes, but to the truth inside them.

Host: And in that still moment, Peabo Bryson’s words found their echo —
that hipness isn’t borrowed or bestowed,
but created, quietly, defiantly, from within.

Host: For some chase trends.
Some chase time.
But the rare ones — the truly hip ones —
simply live in rhythm with their own soul.

Host: And that, Jack finally realized,
was the coolest thing of all.