As far as cities, one of my favorite stops every year is Rome I

Host: The sun was sinking behind the ancient skyline of Rome, painting the stones gold and the air with a faint hum of eternity. The city pulsed like a living relic — scooters darting through cobbled alleys, church bells echoing off marble walls, laughter spilling from cafés where the wine never stopped breathing. The Tiber River shimmered like molten bronze beneath the bridges that had seen empires rise and fall.

Jack and Jeeny sat on the steps of Piazza del Campidoglio, tennis bags at their feet, the sound of distant applause from the Foro Italico still lingering in their ears. The evening air was warm, fragrant with basil and rain, and the street below was alive with musicians — Rome itself, serenading them.

Jeeny: “Madison Keys once said, ‘As far as cities, one of my favorite stops every year is Rome. I think it’s super fun to play there, because the tournament is really cool and the fans are super engaged, but also you get to walk around going to dinner, and the history — it’s truly one of the most amazing cities in the world. I love it.’”

Host: Jack leaned back on his elbows, his grey eyes watching a group of kids chasing a soccer ball across the square. He smiled — not with irony this time, but with something gentler.
Jack: “She’s right. Rome doesn’t just host tournaments — it hosts time itself. You feel it everywhere, like the city’s playing its own eternal game.”

Jeeny: “Exactly. It’s not just the matches. It’s the layers — the way history sits beside espresso, beside laughter, beside the roar of the crowd.”

Jack: “Every stone here’s a witness. Every street’s a victory lap for someone — emperors, poets, gladiators, or tennis players.”

Jeeny: “That’s what makes it amazing — the overlap. You win a set, then you walk out and have dinner where Caesar planned a conquest.”

Jack: “Or maybe just pasta.”

Jeeny: “Same difference.”

Host: The wind picked up, carrying the faint sound of a violin from somewhere near the Forum. A couple strolled past, hands intertwined, whispering in Italian — that rhythm of speech that sounds like music and argument in equal measure.

Jack: “You know what I like about what Keys said? It’s not about the glamour of the sport. It’s about gratitude. She’s talking about the privilege of being alive in a place like this.”

Jeeny: “And being part of something ancient — competition, performance, art — all woven together. Rome’s always been a stage, hasn’t it?”

Jack: “Always. From the Colosseum to the clay courts. The difference is the weapons changed.”

Jeeny: “Now it’s racquets and applause instead of swords and cheers.”

Jack: “And the crowd still wants the same thing — spectacle.”

Jeeny: “But it’s not cruel anymore.”

Jack: “You sure about that? The internet can be a pretty ruthless arena.”

Jeeny: “Touché.”

Host: The sky deepened into indigo, the first stars timidly showing themselves above the domes. The city lights flickered on, golden and forgiving.

Jeeny: “It’s funny — people come here to see ruins, but nothing about this place feels ruined. It’s alive. Like history learned how to breathe again.”

Jack: “That’s because Rome doesn’t mourn its past — it celebrates it. Every broken pillar, every faded fresco — it’s all part of the rhythm.”

Jeeny: “That’s what art does — it makes decay beautiful.”

Jack: “And what sport does — it makes effort eternal.”

Host: Jeeny smiled, tucking her hair behind her ear as she looked out over the rooftops.
Jeeny: “You think that’s why she loves playing here so much? Because Rome matches her — elegance with endurance.”

Jack: “Maybe. Rome’s like an athlete too — scarred, stubborn, graceful, still competing with time.”

Jeeny: “And still winning.”

Jack: “Always.”

Host: A waiter walked past carrying a tray of wine glasses, the scent of Chianti trailing behind him. Somewhere nearby, a street performer began to sing — low, melodic, ancient. Jeeny closed her eyes for a moment, letting the music settle around her.

Jeeny: “You know, there’s something spiritual about cities like this. They remind you that greatness doesn’t have to be new — it just has to be alive.”

Jack: “And that beauty doesn’t come from perfection, but from persistence.”

Jeeny: “Exactly. That’s Rome — imperfect, chaotic, magnificent. The city’s not trying to impress anyone. It just is.”

Jack: “That’s why it’s timeless. It’s confident enough to crumble.”

Jeeny: “And still be adored.”

Host: A pause stretched between them — not silence, but fullness. The kind of quiet that carries meaning without needing words. Jack leaned forward, elbows on his knees.
Jack: “You ever think about how many people have stood right here, saying the same thing? Poets, lovers, travelers — all trying to describe what can’t be described.”

Jeeny: “That’s why people keep writing about Rome. It refuses to fit into a sentence.”

Jack: “Even Keys — she wasn’t trying to sound profound. She just said what everyone feels here: it’s amazing.”

Jeeny: “And honest. She wasn’t talking about monuments. She was talking about the feeling. The way the city makes you feel infinite and small at the same time.”

Jack: “Like winning and losing on the same day.”

Jeeny: “Like life.”

Host: The church bells began to ring in the distance — long, rolling tones that drifted over the rooftops like slow thunder. Jack glanced toward the sound, his expression softening.
Jack: “You know, every great city has a heartbeat. But Rome — Rome has a soul.”

Jeeny: “A big, messy, beautiful soul.”

Jack: “One that doesn’t care if you understand it — only that you feel it.”

Jeeny: “And you always do.”

Host: The bells faded, replaced by the whisper of evening — footsteps, laughter, the clink of cutlery, the low hum of stories still being written. Jeeny stood, stretching, her silhouette outlined by the glow of streetlights.

Jeeny: “I think Madison Keys said it perfectly — it’s not just about history or beauty. It’s about connection. Rome doesn’t let you pass through; it pulls you in.”

Jack: “Yeah. You don’t just visit Rome — you join it.”

Jeeny: “For a meal, a match, or a lifetime.”

Jack: “And it never lets you forget.”

Host: The two of them gathered their bags, walking down the marble steps toward the hum of the city below. The cobblestones gleamed from a light drizzle, catching reflections of storefronts, statues, and headlights — ancient and modern light coexisting on wet stone.

Jeeny looked back once at the skyline — the domes, the ruins, the eternal glow.
Jeeny: “You know, if cities could sing, Rome would sound like this night.”

Jack: “And every note would say, ‘I’m still here.’”

Host: They disappeared into the narrow streets, laughter trailing behind them, blending with the sounds of a city that never truly sleeps — only waits for the next story to unfold.

And as the wind carried the faint echo of the crowd still cheering somewhere near the clay courts, the truth of Madison Keys’s words shimmered through the Roman night —

that some places aren’t just visited,
they’re felt.

That Rome is not a destination,
but a dialogue — between past and present,
between beauty and endurance,
between every soul that ever dared to say,
“I love it.”