I have a tendency to sabotage relationships; I have a tendency to

Host: The night hung heavy over the city, its skyline a silhouette of half-lit windows and sleeping dreams. Inside a dim bar tucked beneath an old brick building, the air was thick with the scent of whiskey and regret. A single neon sign flickered — Open Late — its light pulsing like a tired heartbeat.

Host: Jack sat at the counter, a glass of bourbon untouched before him. His jawline clenched tight, his eyes grey and distant. Jeeny sat across from him, her small hands wrapped around a chipped cup of coffee, steam curling between them like ghosts of unspoken words.

Jeeny: (quietly) “Michael Bublé once said, ‘I have a tendency to sabotage relationships; I have a tendency to sabotage everything. Fear of success, fear of failure, fear of being afraid. Useless, good-for-nothing thoughts.’”

Host: The words hung in the air, fragile, trembling like a thread stretched between confession and surrender.

Jack: (gruffly) “He’s not wrong. That’s the real disease — not failure, not heartbreak. Just… fear. The kind that keeps you from even trying.”

Jeeny: “But isn’t that the same as dying before you’re dead, Jack? To live in fear of feeling, to stop before you begin — it’s like pulling the plug on your own heart.”

Host: The bartender wiped down the counter, the rhythmic motion of the rag sounding almost like the ticking of a clock. Time itself seemed to be listening.

Jack: “You think fear is some poetic tragedy. It’s biology. Self-defense. You get burned enough times, you learn not to touch the fire.”

Jeeny: “But if you never touch the fire again, how do you stay warm?”

Host: The question slipped through the silence like a blade through silk. Jack’s fingers tightened around his glass, his knuckles white.

Jack: “Warmth isn’t worth the burns. You think courage means ignoring the pain, but it’s just stupidity dressed up as hope.”

Jeeny: “No, Jack. It’s faith dressed up as defiance. You talk like a man who’s already accepted his sentence. But what if sabotage isn’t self-defense — what if it’s self-punishment?”

Host: The light from the bar’s window caught her face, and for a moment, her eyes glowed with something fierce — not anger, but compassion sharpened into truth.

Jack: (after a pause) “You think I don’t know that? Every time something good starts, I can already see the ending. So I end it first. Before it leaves me.”

Jeeny: “That’s not control, Jack. That’s surrender disguised as strength.”

Host: Outside, a train roared in the distance — a low, trembling sound, like the city itself was sighing. The neon light flickered again, washing them both in blue.

Jack: “You ever notice how the best things in life demand the most of you? Love, work, dreams — they all ask you to risk everything. And the moment you give in, they find a way to hurt you.”

Jeeny: “But isn’t that what makes them real? Pain doesn’t cancel meaning, Jack. It proves it existed.”

Host: Jeeny’s voice was soft, but it carried the weight of someone who had been broken and rebuilt, piece by fragile piece.

Jeeny: “You remember Vincent van Gogh? He painted the stars while losing his mind. He didn’t paint because he was sane. He painted because that was the only way to stop drowning. His art was both the wound and the bandage.”

Jack: (bitter smile) “And it killed him in the end.”

Jeeny: “No. The silence did. The part of him that no one wanted to hear.”

Host: The rain began to fall, slow at first, then heavier, each drop tapping against the window like restless fingers. The bar grew quieter.

Jack: (looking down) “You think fear can ever go away?”

Jeeny: “No. But it can learn its place. It’s not supposed to drive; it’s supposed to ride shotgun.”

Jack: “And what if it refuses?”

Jeeny: “Then you teach it. Every time you choose to stay instead of run, to love instead of hide — you teach it who’s in charge.”

Host: Jack’s eyes lifted, his expression unreadable — part cynic, part child lost in memory. The glass trembled slightly in his hand.

Jack: “You make it sound easy.”

Jeeny: “It’s not. That’s why most people never learn. Fear is seductive — it promises safety but steals your life in small, quiet pieces.”

Host: Jeeny leaned forward, her voice almost a whisper now, intimate and raw.

Jeeny: “Tell me, Jack. When was the last time you let yourself be loved without calculating the exit?”

Jack: (after a long silence) “Maybe never.”

Host: A faint hum filled the room — the kind of quiet that feels louder than any sound. The clock on the wall ticked once, twice.

Jeeny: “Then maybe the real sabotage isn’t fear of losing. It’s fear of being seen.”

Host: Jack looked at her, eyes heavy with the kind of truth a man doesn’t want but can’t deny. His voice dropped low, almost breaking.

Jack: “You ever look in the mirror and feel like the person staring back isn’t someone you deserve to be?”

Jeeny: “All the time. But I still look. That’s the difference between hating yourself and trying to love yourself.”

Host: The rain softened. The neon light flickered one last time, then steadied.

Jack: (half-smiling) “You talk like you’ve never sabotaged anything.”

Jeeny: “I have. Plenty. But I stopped calling it fate. I started calling it fear. It’s easier to fight something when you name it.”

Host: The bartender turned off the radio, leaving the soft hum of the refrigerator as the only sound. Jeeny sipped her coffee, watching Jack with quiet patience.

Jeeny: “You know, success frightens people more than failure. Failure confirms what they already believe — that they’re not enough. But success? Success asks for transformation. It demands that you outgrow your old wounds.”

Jack: “And some wounds are comfortable.”

Jeeny: “Exactly. That’s why we cling to them. They remind us who we were when no one else was watching.”

Host: The rain stopped completely now, and the city outside began to glow — reflections of streetlights trembling in puddles like fractured constellations.

Jack: “So what do you do when the fear comes back?”

Jeeny: “You let it. But you don’t feed it. You tell it: I see you. But I’m moving anyway.”

Host: The silence after her words felt like a kind of peace. Jack looked down at his empty glass, then at Jeeny, and for the first time, his eyes softened.

Jack: “You make it sound like there’s still time.”

Jeeny: “There always is — until you stop believing there is.”

Host: Outside, a train horn echoed again, this time distant, almost like a farewell. Jack stood slowly, placing a few bills on the counter, his movements deliberate, thoughtful.

Jack: “Maybe next time, I’ll try not to sabotage it.”

Jeeny: (smiling faintly) “Maybe next time, you’ll let yourself win.”

Host: As they stepped outside, the air was cool and clean, the rain now just a memory. A soft wind brushed past, carrying the faint smell of earth and light. The streetlights shimmered above them, tiny halos on the wet pavement.

Host: Jack looked up at the sky, and for a fleeting moment, something like calm crossed his face — a man no longer at war with himself, but not yet at peace either. Somewhere between fear and freedom.

Host: Jeeny walked beside him, her steps steady, her shadow merging with his. Together, they disappeared down the quiet street, two silhouettes beneath a city learning how to breathe again.

Host: And as the last light faded from the bar window, the neon sign flickered one final time — Open Late — before going dark. Only the word Open remained, glowing faintly in the night.