The best time to buy a home is always five years ago.

Host: The rain was falling hard — that rhythmic, hypnotic kind of rain that made the city look half-washed, half-dreamed. The real estate office sat on the corner of a dimly lit street, its glass windows fogged from the inside, reflecting rows of empty desks and framed photos of smiling couples holding keys under blue skies.

It was late. The neon “SOLD” sign in the window flickered intermittently, like a heartbeat unsure if it wanted to keep going.

Jack sat in one of the cubicles, sleeves rolled up, a pile of brochures spread before him — all the glossy lies of ownership: perfect lawns, bright kitchens, couples caught mid-laughter. His expression was one of reluctant irony.

Jeeny walked in, shaking off an umbrella, rain still caught in her hair. She wore no pretense of the corporate grin the posters demanded. She walked straight to Jack’s desk, sat on its edge, and said the line that would become the night’s truth.

Jeeny: “Ray Brown once said, ‘The best time to buy a home is always five years ago.’”

Jack: (smirking) “Ah yes — the real estate prophet. Or the pessimist with a calculator.”

Jeeny: (laughing) “Or maybe the realist. The kind that knows hindsight pays better than advice.”

Jack: “So basically, we’re all five years too late for something.”

Jeeny: “Exactly. That’s the joke and the lesson.”

Host: She leaned back slightly, eyes wandering to the rain streaking down the glass. The reflection of the streetlights painted her face in silver and shadow.

Jack: “You think he meant it literally? Or philosophically?”

Jeeny: “Both. Property or purpose — it’s all about missed timing. People only see value once it’s gone.”

Jack: “You’re saying we’re cursed to recognize opportunity only in the rearview mirror?”

Jeeny: “No, I’m saying we mistake patience for paralysis. We wait for certainty, but certainty only shows up after the chance has expired.”

Host: Her words landed like quiet thunder — not loud, but resonant. Jack leaned back, tapping a pen against the table.

Jack: “You sound like someone who’s lost a few chances.”

Jeeny: “Haven’t we all? Houses. Jobs. People. Timing’s the cruelest landlord — always charging late fees on regret.”

Jack: (grins faintly) “That’s poetic. Should I write it on our next brochure?”

Jeeny: “You should write it on your conscience.”

Host: The rain softened. The office lights dimmed on a timer, leaving the room half-shadowed. Papers on the desks fluttered faintly under the hum of the air conditioner.

Jack: “You know, there’s something absurd about all this — about selling permanence in a world that moves so fast. You buy a home for stability, and then the market shifts, the neighborhood changes, life outgrows it.”

Jeeny: “Maybe the house isn’t what’s supposed to stay still — maybe it’s you.”

Jack: (looking at her) “And if I don’t?”

Jeeny: “Then you keep renting your life — moving from moment to moment, waiting for the perfect one that never comes.”

Host: A silence fell — not uncomfortable, but contemplative. The kind that made the ticking of the clock sound louder, like time mocking the indecision of human beings.

Jeeny stood, walked to the window, and traced a finger along the condensation.

Jeeny: “You know what Ray Brown’s quote really means to me? It’s not about houses at all. It’s about commitment. Every meaningful thing in life has that same principle — the best time to start was always five years ago.”

Jack: “Relationships. Dreams. Health. Hell, even happiness.”

Jeeny: “Exactly. We think we’re protecting ourselves by waiting. But what we’re really doing is starving our future.”

Host: Her reflection in the glass looked like a double exposure — her and the storm, both caught between stillness and motion.

Jack: “You ever wish you’d started something earlier?”

Jeeny: (quietly) “Everything.”

Jack: (nods) “Same.”

Jeeny: “But wishing’s a tax on time you can’t get back.”

Host: The neon “SOLD” sign flickered again, lighting the room in pulses — red, then dark, then red again. It cast both of them in a strange rhythm, like actors caught between frames.

Jack: “You know, I’ve sold hundreds of homes. Families walk in, nervous but hopeful. They’re never thinking about the mortgage, or the market. They’re thinking about Sunday mornings — light through the window, laughter in the kitchen. That’s what they’re buying.”

Jeeny: “And what are you selling?”

Jack: (pauses) “Security, maybe. Or the illusion of it.”

Jeeny: “You can’t sell something that doesn’t exist. You can only sell the promise of trying.”

Host: Her voice was gentle, but it carried truth like a blade wrapped in velvet. Jack stared at his papers, the faces in the brochures smiling back at him — perfectly posed, perfectly happy, perfectly impossible.

Jeeny: “You ever notice how every house ad uses sunlight? No one ever shows the rain. No one ever shows the cracks in the walls or the silence after the fights.”

Jack: “Because people don’t buy homes — they buy hope.”

Jeeny: “Exactly. And the best time to buy hope was always five years ago too.”

Host: A laugh escaped her, soft and sincere. Jack smiled — the kind of smile that carried both fatigue and fondness.

Jack: “You think there’s still time?”

Jeeny: “There’s always time. Just never enough certainty.”

Jack: “Then maybe the lesson is to start anyway — to buy into something before you can afford to be sure.”

Jeeny: “That’s not just real estate advice, Jack. That’s life.”

Host: Outside, the rain stopped. The streets gleamed — clean, reflective, forgiving. The city lights shimmered across puddles like scattered constellations, proof that even after the storm, the world kept trying to shine.

Jack stood and walked toward the window beside her. They stood shoulder to shoulder, watching the street below.

Jack: “You know, it’s funny — all the people who waited, thinking they’d get a better deal… they end up paying more in the end.”

Jeeny: “Because fear inflates cost. Action deflates it.”

Jack: “You really believe that?”

Jeeny: “Completely. You either pay now with courage, or pay later with regret.”

Host: The rain began again — soft, rhythmic, patient.

Jeeny turned toward him, her expression warm, steady.

Jeeny: “So, Jack… what’s the house you’ve been too afraid to buy?”

Jack: (after a pause) “My own future, I guess.”

Jeeny: “Then stop renting it.”

Host: The neon sign flickered once more, then held steady. The hum of the city grew softer, as though even the streets were listening.

And in that small, fluorescent room filled with the ghosts of sold dreams and waiting signatures, the wisdom of Ray Brown found its truest echo:

That the best time to begin anything worth having —
a dream, a love, a home, a life —
is always five years ago.

That hesitation is the most expensive thing we’ll ever buy,
and the only thing that depreciates faster than property
is time.

And that the real investment
is not in bricks or land or equity —
but in the simple, terrifying act
of saying yes
while you still can.

Host: The city lights blurred in the glass.
Two silhouettes stood still —
not waiting anymore,
just deciding.