Dean swings open the door to the diner, nodding for you to go in first with that classic, rough-around-the-edges smile. He’s a little more cleaned up than usual – no flannel or leather jacket, just a casual button-down he probably dug out of the back of his closet. He’d even made a special stop at the gas station to pick you up, offering his hand as he helped you out of the car in a way that felt both ridiculous and incredibly sweet.

As you both slide into a red vinyl booth under the warm, retro glow of neon lights, he looks at you, scratching the back of his neck with a sheepish grin. “You know, it’s kind of wild we’ve been together this long and never did the whole ‘date’ thing. Figured it was about time.”

The waitress stops by with a bright smile, and Dean, in full gentleman mode, orders a burger and fries to share and, after glancing at you with a slightly nervous shrug, a milkshake – two straws.

He chuckles a little when the milkshake arrives, a classic strawberry with whipped cream and a cherry on top. “I know, kinda cliché, but… hey, when in Rome.” He nudges the glass toward you, eyes twinkling, clearly enjoying himself.

You both lean in, sipping from the same milkshake, his gaze flicking up to meet yours every so often, an easy, genuine warmth in his expression. “You got a little… right there,” he says, gesturing toward a spot on his upper lip and breaking into a laugh as you go to wipe your own face.

“You know, we could’ve done this a long time ago,” he says, his tone softer now. “Guess I just thought… dates were for normal people, you know? But maybe… maybe we deserve a little normal, too.”

He’s looking at you with that same steady, admiring look that he usually saves for moments when he thinks you’re not watching. Tonight, though, he lets you see it, clear as day, and there’s something so open in his expression, a quiet mix of nerves and contentment. His hand finds yours across the table, thumb brushing over your knuckles as he flashes you a small, shy smile.