You have to pretend that your life is a financial pleasure even

Host: The neon hum of the city bled through the narrow window of a third-floor bar, the kind that pretended to be timeless and failed beautifully. The smell of old whiskey, dust, and tired hope hung in the air. It was nearly midnight. The rain had just stopped, leaving the pavement slick and reflective, like a mirror no one wanted to look into.

At the corner booth, Jack sat — tall, tired, grey-eyed — with his jacket folded neatly beside a half-empty glass. Across from him, Jeeny stirred the last of her coffee, her fingers trembling just enough to betray her calm.

They’d been talking for hours. About everything and nothing. But now, the topic had turned to Kinky Friedman — and his bitter, laughing truth: “You have to pretend that your life is a financial pleasure even when your autographs are bouncing.”

Jeeny: “I love that line. It’s tragic and funny at the same time. The kind of truth you can only say with a grin — when you’ve already fallen, but you want people to think you’re still dancing.”

Jack: “Or it’s just denial. Pretending success while drowning in debt. That’s not poetry, Jeeny — that’s survival wrapped in sarcasm.”

Host: A bartender walked past, the glasses clinking softly, the jukebox murmuring some forgotten blues tune. The light above their table flickered, as if even the electricity was tired of lying.

Jeeny: “Maybe survival is poetry, Jack. Maybe the whole act of pretending — keeping the smile when the bank calls, when your cards get declined, when your dreams are one rent payment away from vanishing — maybe that’s its own kind of courage.”

Jack: “Courage? You think faking stability is courage? It’s theater. Everyone out there pretending they’ve got it figured out, buying drinks they can’t afford, posting pictures that lie. We’ve built an entire culture on appearances. It’s not brave — it’s pathetic.”

Host: Jack’s voice was low, but it carried weight, like a knife against velvet. Jeeny leaned back, watching the rainlight flicker against the window.

Jeeny: “You ever think that maybe pretending isn’t lying — maybe it’s protecting yourself? Think about Kinky Friedman — a musician who never quite fit the mold, a writer who turned failure into a joke. When he said that line, he wasn’t boasting — he was confessing. He was saying: I’m broke, but I’ll laugh before I cry. Isn’t that more honest than despair?”

Jack: “Honest would be admitting the failure without dressing it up in irony. All that ‘fake it till you make it’ nonsense has turned people into walking performances. There’s nothing noble about pretending to be okay. It’s the death of authenticity.”

Jeeny: “No, it’s the cost of dignity. You call it performance — I call it poise. People wear masks not because they want to deceive, but because the world punishes rawness. Look at anyone trying to build a dream — the artist, the small business owner, the parent who can’t afford their kid’s medication — they all have to act like they’re doing fine. Otherwise the wolves come closer.”

Host: A train rumbled in the distance, a slow mechanical growl cutting through the night. Jack’s hands tightened around his glass. The liquid trembled slightly, catching the light.

Jack: “You sound like my father. He used to say, ‘Never let them see you sweat.’ And he died sweating — heart attack on a construction site. Still had his tie on.”

Jeeny: “Then maybe he died with dignity. That tie was his way of saying: I’m not beaten. The world didn’t get the last word.”

Jack: “The world always gets the last word, Jeeny. That’s the problem.”

Host: The silence between them pulsed — thick, electric, almost alive. Outside, a taxi honked, and the reflection of red taillights spilled across the wet floor, painting their shadows crimson.

Jeeny: “You ever heard of F. Scott Fitzgerald’s last years? He was living in Hollywood, broke, forgotten, writing screenplays no one read. He’d sign autographs for fans — and those same autographs were bouncing at the bank. He pretended to still be the golden boy of the Jazz Age. But you know what? He kept writing. Even broke, even broken. That’s the kind of pretending Friedman meant.”

Jack: “Fitzgerald died thinking he was a failure.”

Jeeny: “And we remember him as one of the greats. Maybe that’s the point. You pretend long enough, and sometimes the world catches up to the version you were pretending to be.”

Host: The bartender refilled their glasses without a word. The ice clinked, and the sound lingered — like a heartbeat in an empty room.

Jack: “So you’re saying illusion can create reality? That’s a dangerous line, Jeeny. That’s how we end up with fake gurus, empty influencers, and politicians selling fantasy as fact.”

Jeeny: “There’s a difference between performance and delusion. The first keeps you moving — the second keeps you blind. Friedman wasn’t lying about success; he was laughing at the absurdity of chasing it. You have to pretend, because if you stop pretending, you stop creating.”

Jack: “That’s idealism with a hangover.”

Jeeny: “Maybe. But even idealism with a hangover can sing.”

Host: The rain began again — soft, insistent — tapping against the window like a rhythm that refused to end. The bar seemed smaller now, more intimate, like a confession booth.

Jack: “You really think this ‘pretend success’ game is healthy? I see people go broke chasing images of themselves. They spend what they don’t have to look like what they aren’t — and then call it resilience.”

Jeeny: “Maybe that’s because the world only listens when you look successful. No one funds failure, Jack. No one hires honesty. You wear the mask until you can afford to take it off.”

Jack: “And what if you never can?”

Jeeny: “Then at least you lived with style.”

Host: Jack let out a low laugh, dry as paper. It wasn’t joy — it was surrender.

Jack: “You’re impossible.”

Jeeny: “No, just tired of seeing good people drown quietly because they thought dignity wasn’t worth the lie.”

Host: The clock above the bar struck one. A single neon sign buzzed and dimmed, painting their faces in blue.

Jack: “You know what’s funny? I think I used to believe that too. That pretending could buy time. But after years of acting fine, you forget where the mask ends. You lose the real face underneath.”

Jeeny: “Then maybe pretending isn’t about the face. Maybe it’s about the heart. You keep smiling until it believes the smile.”

Host: The music changed — a slow, tired guitar, playing something that felt like both a goodbye and a beginning.

Jack: “So what are we pretending for now, Jeeny?”

Jeeny: “Maybe just for the right to keep trying. Maybe that’s all any of us can afford.”

Host: The light caught her eyes, and for a moment, they glowed — full of warmth and defiance. Jack’s expression softened, a rare crack in his armor.

Jack: “You really believe pretending can save you?”

Jeeny: “No. But it can save the dream long enough for reality to show up.”

Host: The rain stopped. Outside, the city shimmered — not new, but somehow renewed. The pavement glowed like silver, and a faint fog curled through the streetlights, softening everything it touched.

Jack stood, tossing a few crumpled bills on the table — too few to cover the drinks, but enough to make it look like he tried.

Jeeny smiled, shaking her head.

Jeeny: “See? Even now, pretending.”

Jack: “Guess Friedman was right. We’re all performing solvency in the theater of collapse.”

Jeeny: “And some of us still find the courage to bow before the curtain falls.”

Host: They walked into the wet street, their reflections trailing behind like forgotten ghosts. The city exhaled — smoke, light, and music rising into the night — and somewhere, far off, the echo of laughter lingered, the kind that hurts a little because it knows the truth:

We all pretend to be rich in purpose, even when our autographs are bouncing.