You never thought you’d see Chuck Bass behind the wheel of an old black Aston Martin, wind in his hair and not a skyscraper in sight. But there he was—smirk in place, sunglasses reflecting the Italian countryside—as if the entire world was just another deal he’d already closed.

It started when you needed a break. Life in Manhattan had become suffocating—endless deadlines, drama, and the same skyline that once thrilled you now felt like a cage. Chuck had seen it in your eyes before you ever said a word.

“You need to get out,” he’d said, leaning against his bar at The Empire. “So do I. Europe, maybe? Just… drive until we run out of roads.”

“You’re serious?”

“Deadly. Pack a bag.”

Two days later, you were standing with him in Paris, your passport barely stamped before you were in his car, no schedule, no destination—just the hum of the engine and the soft chaos of his presence.

The first few days were quiet. Chuck wasn’t one for small talk when the scenery could do it for him. But somewhere between the vineyards of France and the cobbled streets of Prague, you saw something no one in New York ever had—the real him.

He still had his sharp tongue, of course.

"You really think you can outdrive me?” he’d tease whenever you tried to take the wheel.

“You’re not the only one who knows how to take control, Bass.”

“Careful. I might like the competition.”

Every stop felt like a story—nights spent in small hotels under fake names, mornings wandering marketplaces where nobody cared who you were. He’d buy you coffee, always black and strong, and tell stories about his father, his losses, the world he’d tried to conquer and the parts of himself he couldn’t.

In Florence, he kissed you for the first time—under a balcony lit by streetlamps, laughter echoing through narrow alleys. It wasn’t planned, it wasn’t polished. It was real. And that scared you both.

“This was supposed to be a distraction,” you whispered.

“It still can be,” he said softly, brushing your hair back. “Or it can be something worth remembering.”

By the time you reached the coast of Spain, the line between adventure and intimacy had blurred completely. Nights turned to stolen moments in candlelit rooms. Days were spent chasing sunsets, his hand occasionally finding yours across the console.

But as the trip drew closer to its end, reality loomed. Manhattan would still be there—the business, the expectations, the people who would never understand this version of him, or of you.

"What happens when we go back?” you asked one night, sitting on the hood of the car overlooking the ocean.

“We don’t,” he said simply, taking your hand.

“Not really. Maybe the city gets us back… but we leave the best parts of ourselves here.”