I have in the past overly trusted people and was, in turn, let

Host: The rain had stopped, but the pavement still glistened — a mirror of the city lights, fractured by puddles and footsteps. The air outside the café was cool and heavy, touched with the faint smell of espresso and asphalt. Inside, the night hummed quietly: a few late customers, the hiss of the coffee machine, and a jazz tune spinning softly in the background.

By the window, Jack sat with his hands wrapped around a mug, the steam curling upward like memory. His reflection — half shadow, half light — blurred in the glass. Across from him, Jeeny rested her chin in her palm, a half-smile on her lips, her eyes clear and steady, like she could see the truths hiding behind his silence.

Jeeny: “Do Won Chang once said, ‘I have in the past overly trusted people and was, in turn, let down by some. Since then, I have learned the difference between putting faith into people and blindly trusting them.’”

Jack: sighing softly “That’s a lesson they don’t teach in business school — or anywhere else that pretends to prepare you for life.”

Jeeny: tilting her head “Because it’s not theory. It’s scar tissue.”

Jack: smirking “And scar tissue doesn’t show up on résumés.”

Host: The café door opened briefly, a gust of wind sweeping through — carrying the smell of rain, damp coats, and passing ambition. Jack glanced toward it, then back at Jeeny. The light from the hanging lamp flickered over his features — the sharp lines of cynicism softened by something weary but kind.

Jack: “You know what’s funny? Everyone tells you to trust — your team, your partners, your gut. No one tells you that trust’s the fastest way to get cut open.”

Jeeny: “Only if you confuse trust with surrender.”

Jack: raising an eyebrow “Is there a difference?”

Jeeny: “Yes. Trust says, ‘I see who you are, and I choose to believe in you anyway.’ Blind faith says, ‘I’ll close my eyes and hope you don’t hurt me.’”

Jack: pausing, thoughtful “So one’s love, and the other’s denial.”

Jeeny: “Exactly.”

Host: The rain began again, a soft drizzle tapping against the windowpane. The city lights blurred into watercolor — red, gold, blue — like emotion itself spilling beyond its edges.

Jack: “You know, I used to think trust was binary — you either did or you didn’t. But maybe it’s more like balance. Too little, and you live guarded. Too much, and you live wounded.”

Jeeny: “And the right amount means you live awake.”

Jack: half-smiling “Awake’s overrated. Sleep is safer.”

Jeeny: smiling back “But sleep doesn’t build anything. Chang didn’t found an empire by hiding behind closed eyes.”

Host: The steam rose from their cups, the air thick with warmth and words. Outside, a passerby held an umbrella that caught the neon light, glowing faintly like a halo — fragile, fleeting, human.

Jack: “You ever think about how trust feels like risk disguised as virtue?”

Jeeny: “Because it is. Every time you trust, you gamble on humanity — theirs and your own.”

Jack: “And what happens when you lose?”

Jeeny: “You don’t stop playing. You just learn how to read the table better.”

Host: The music in the café shifted, a saxophone now — slow, melancholic, full of longing. Jack leaned back, eyes tracing the ceiling, his voice quieter, almost confessional.

Jack: “I used to trust people like they were safety nets. I thought good intentions guaranteed good outcomes.”

Jeeny: softly “That’s the most dangerous belief in the world.”

Jack: “Yeah. I found that out the hard way. The higher you climb, the more the fall hurts — especially when the ones who let you drop smile on the way down.”

Jeeny: after a pause “But here you are. Still building. Still showing up. That’s faith, Jack — not blindness.”

Host: The rain thickened, the sound rhythmic and grounding. The reflection of the city rippled across the window like an echo of something unspoken. Jeeny took a sip of her tea before continuing, her voice quiet but certain.

Jeeny: “You know, I think that’s what Chang was really saying — that faith in people isn’t about believing they won’t disappoint you. It’s about trusting that you’ll survive it when they do.”

Jack: nodding slowly “And maybe come out wiser.”

Jeeny: “Wiser — but not colder. That’s the trick.”

Jack: with a faint smile “You make it sound easy.”

Jeeny: grinning “If it were easy, it wouldn’t be worth learning.”

Host: The lights dimmed slightly, the café now bathed in gold and shadow. Outside, the streetlights reflected on the puddles like tiny constellations scattered across the asphalt. The rain slowed, and in the stillness between drops, Jack’s voice cut softly through.

Jack: “You ever forgive someone who broke your trust?”

Jeeny: after a moment “Yes. But not for them — for me. Because forgiveness is the only way to keep the door open without walking through it again.”

Jack: “So forgiveness isn’t reconciliation.”

Jeeny: “No. It’s release.”

Host: A long silence settled. The world outside felt far away now — just rain, just light, just the hum of the espresso machine. The moment between them carried the weight of shared experience, not as confession, but as recognition.

Jack: “You know, sometimes I think people like Chang — the ones who build from nothing — trust because they have to. Because if you don’t believe in others, you end up alone, and alone can’t build empires.”

Jeeny: smiling softly “And yet, they still learn the cost.”

Jack: “Maybe the cost is the proof. You can’t know integrity without betrayal.”

Jeeny: nodding slowly “And you can’t know wisdom without pain.”

Host: The rain finally stopped, the city exhaling as if relieved. Jack glanced at the empty mug before him, then at Jeeny, and for the first time all night, his expression softened completely.

Jack: “You know, maybe trust isn’t a weakness after all. Maybe it’s a kind of courage — the quiet kind.”

Jeeny: smiling “The bravest kind. The kind that risks being let down — and still keeps believing.”

Host: The street outside gleamed, reborn under the lamplight. People hurried past, their reflections fleeting but real. The night felt lighter now, less about pain and more about resilience — the kind that grows in silence, in patience, in lessons learned the hard way.

As they rose to leave, their footsteps echoed faintly against the tile — the sound of two people who knew that even disappointment could be a teacher.

And as they stepped into the cool air, the words of Do Won Chang lingered between them like a benediction — not bitter, not naïve, but earned:

That trust is not blindness,
but bravery with boundaries.

That to believe in people again after betrayal
isn’t weakness —
it’s wisdom learning to breathe.

And somewhere in the glow of that rain-washed night,
Jack smiled — not at Jeeny, not at the past —
but at the quiet, stubborn truth of it all:

To trust again is to begin again.