I assume everything I do in life is gonna be a failure, and then

Host: The city night glowed in muted orange, the rain falling slow and steady over dim streetlights. A lonely diner sat at the corner, its neon sign flickering, humming faintly like the pulse of insomnia. Inside, the smell of burnt coffee lingered — familiar, weary, oddly comforting.

At a booth near the window, Jack sat hunched, his hands wrapped around a chipped mug, the kind of man who’d learned to measure hope in spoonfuls. Across from him, Jeeny stirred her tea slowly, her eyes bright yet pensive, the kind of woman who could find beauty even in a confession of defeat.

The rain tapped gently on the glass, like time itself whispering reminders of how fragile we all are.

Jeeny: “Jonah Hill once said, ‘I assume everything I do in life is gonna be a failure, and then if it turns up roses, then I’m psyched.’”

Jack: smirking slightly “Ah, a realist after my own heart.”

Host: The diner light flickered, catching the faint steam rising from his cup, turning it into a ghost of warmth.

Jeeny: “Realist? No. That’s someone protecting himself from disappointment.”

Jack: “Same difference. You can’t be disappointed if you never expect much.”

Jeeny: “And you can’t really live if you never expect anything at all.”

Host: The rain deepened, its rhythm heavier now, a quiet percussion on glass. The world outside blurred — lights melting into each other, reality softening at the edges.

Jack: “Expectations are traps. The higher you climb them, the harder you fall. Failure’s inevitable — better to make peace with it than pretend it won’t come knocking.”

Jeeny: “But if you live assuming failure, you stop aiming for anything worth falling for.”

Jack: “That’s not true. I aim. I just don’t miss sleep if I don’t hit.”

Jeeny: “That’s not peace, Jack. That’s resignation.”

Jack: dryly “Maybe they’re the same thing. I’ve learned to lower the volume on hope — it’s quieter that way.”

Host: Jeeny leaned forward, her eyes steady, the way someone looks when they’re trying to peel truth from someone else’s armor.

Jeeny: “You’re afraid.”

Jack: “Of what?”

Jeeny: “Of wanting. Because wanting means risk. And risk means loss.”

Jack: “No. I’m afraid of wasting time. There’s a difference.”

Jeeny: “No, there isn’t. Both come from the same wound — disappointment.”

Host: The jukebox in the corner came to life suddenly, playing a slow, forgotten tune — something about heartbreak and highways. It filled the silence like a sigh.

Jack: “You ever notice how people romanticize failure? Like it’s some kind of badge of honor? It’s not. It’s just pain wearing better lighting.”

Jeeny: “Maybe. But failure’s the only teacher that doesn’t lie to you. It doesn’t flatter. It just shows you who you are.”

Jack: “Or who you aren’t.”

Jeeny: “Sometimes that’s the same thing.”

Host: Jack stared at her, his expression unreadable, though his eyes softened for the first time that night. He took a slow sip, the coffee bitter and grounding.

Jack: “So you think Jonah Hill’s wrong — that expecting failure isn’t smart?”

Jeeny: “No. I think he’s human. But there’s a difference between being prepared for failure and living inside it before it happens.”

Jack: “You sound like someone who still believes in happy endings.”

Jeeny: “Not endings. Just good chapters.”

Host: The rain softened, turning into mist, the windows fogging slightly. Jeeny traced a shape absentmindedly into the condensation — a small spiral, endless, hopeful.

Jeeny: “You know what I think Hill meant? That he found freedom in detachment. But that freedom’s lonely, Jack. You can’t love the world and assume it’ll fail you at the same time.”

Jack: “Maybe loving the world because it fails you is the point.”

Jeeny: “That’s not love. That’s masochism.”

Jack: laughing quietly “Same thing some days.”

Host: The waitress passed, refilling their cups with practiced indifference. The sound of the pour filled the silence — steady, almost sacred.

Jeeny: “You hide behind irony because it’s safer than sincerity.”

Jack: “Sincerity’s overrated. It gets people hurt.”

Jeeny: “And irony gets them hollow.”

Host: Her words lingered, floating above the steam between them. Jack looked out the window, his reflection merging with the city’s — one man, infinite lives unlived.

Jack: “You ever think failure’s addictive?”

Jeeny: “Only to those who mistake it for identity.”

Jack: “You’re saying some people need to fail?”

Jeeny: “Some people need to stop defining themselves by what breaks them.”

Host: The music faded, replaced by the hum of neon and rain. A soft melancholy filled the space — the kind that feels both familiar and intimate.

Jack: “You make it sound easy. Just stop expecting the worst, right? Like flipping a switch.”

Jeeny: “No. It’s harder. It means risking joy again. It means believing that maybe — just maybe — things can go right.”

Jack: “And if they don’t?”

Jeeny: “Then you get up, call it experience, and try again — but not with bitterness. With grace.”

Host: Jack leaned forward, resting his elbows on the table, studying her face as if searching for the flaw in her faith.

Jack: “You really live like that? Hoping for roses, not expecting thorns?”

Jeeny: “No. I live knowing both exist — and trusting that I’ll bleed and bloom in equal measure.”

Jack: softly “You make failure sound almost holy.”

Jeeny: “Maybe it is. Every failure is proof that you dared. And daring — that’s where living begins.”

Host: The rain stopped, leaving the world slick and glistening, the streets reflecting the diner’s neon sign — “OPEN” — as if the universe were offering a metaphor no one asked for.

Jack: “You think that’s what he meant? That expecting failure was just his way of keeping his heart open without expecting it to be broken?”

Jeeny: “Yes. It’s armor disguised as modesty. But maybe, if you live long enough, you learn to take it off.”

Host: A long silence. Then Jack smiled faintly — not cynical this time, but fragile, real.

Jack: “You know, Jeeny… maybe you’re right. Maybe assuming failure isn’t realism. It’s rehearsal for disappointment.”

Jeeny: “And life deserves better than rehearsal.”

Jack: “Yeah. Maybe it deserves improv.”

Jeeny: “Exactly. That’s how roses happen.”

Host: Outside, the clouds parted, revealing the faint shimmer of moonlight on puddles — each one catching a fragment of light, imperfect but bright. Inside, the diner’s hum softened, the night stretching wide and kind for once.

Jack looked out the window, the city reflected in his eyes — messy, uncertain, alive.

Jack: “Maybe I’ll aim higher tomorrow. Just to see what happens.”

Jeeny: “That’s the spirit.”

Jack: “And if it fails?”

Jeeny: “Then at least it’ll be your own story — not life’s punchline.”

Host: The camera pulled back, the two of them small against the city’s vast glow, framed by neon, steam, and the quiet courage of trying again.

And somewhere between laughter and surrender,
the truth lingered like the aftertaste of coffee and rain —

That expecting failure may protect you from pain,
but only hope, fragile and foolish,
ever turns life into roses.

Fade out.