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The diner Dean picked wasn’t fancy just a little place off the highway with red vinyl booths and a jukebox in the corner. The kind of joint that served burgers with real grease and coffee that could fuel a hunter for a week. It felt right. Familiar. Comfortable.
But nothing about tonight felt comfortable.
Dean Winchester had fought demons, vampires, ghosts, witches, even gods but nothing had prepared him for a quiet corner booth at Rosie’s Diner with Cas sitting across from him and not talking.
Dean shifted in his seat for the third time in as many minutes, one hand rubbing nervously at the back of his neck while the other stayed planted protectively over the pocket of his leather jacket. Inside was a velvet box. And inside that box was a ring.
Across the booth, Castiel Novak sat ramrod straight, blue eyes flickering between Dean and the menu, which he had already read cover to cover. Twice. He wasn't much of a diner food guy, but that wasn’t what had him sweating under the collar of his coat tonight.
He, too, had a ring in his pocket.
"So," Dean said, clearing his throat. His voice cracked slightly, and he mentally kicked himself. “Uh… food’s good here. Real good.”
“Yes,” Cas replied too quickly, nodding. “The… fries. I enjoy the fries.”
Dean stared at him for a second, then gave a half-smile. “You okay, man? You look like someone kicked your puppy.”
Castiel blinked. “I was going to ask you the same thing. You’ve barely touched your beer.”
Dean looked at the sweating bottle on the table like it had betrayed him. “Yeah, just, big night. You know.”
Cas tilted his head, brows furrowed in concern. “Is something wrong?”
“No! No, not… wrong.” Dean rubbed his palms against his jeans. “Just something on my mind.”
Cas studied him carefully. “You seem tense.”
Dean let out a short breath and forced a grin. “What, this?” He shrugged, throwing one arm over the back of the booth like he was trying to fake being relaxed. “Nah, man, just tired. Long week. Demons, salt rounds, ungrateful townies…”
“Dean.”
His name, quiet and steady, stopped him cold. Cas’s voice always did that, somehow gentle and immovable all at once. His eyes were soft but unwavering as he leaned in slightly, elbows on the table.“You don’t have to pretend with me.”
Dean flinched a little. He knew Cas meant well. Hell, he always meant well. That was the problem.
“I’m not pretending,” Dean lied, too quickly. He reached for a fry and tossed it in his mouth, chewing like it might buy him time. “I mean, c’mon, you’re the one who looked like you were going to throw up when the waitress asked if you wanted coffee.”
Cas hesitated, then sat back slowly. “I wasn’t expecting such an aggressive question.”
Dean snorted, grateful for the shift. “Yeah, she really came at you with that coffee pot. Classic sneak attack.”
Cas allowed a small smile to form, the corner of his mouth twitching up. But his eyes still lingered on Dean, watchful.
“You’re deflecting.”
“Damn right I am.” Dean leaned forward, pointing a fry at him. “And I’m damn good at it. Don’t try to out-stubborn me, Cas. It’s a suicide mission.”
Cas didn’t push again. He just sat there, that calm patience radiating off him like a space heater, like he knew Dean was hiding something but wasn’t going to force it. Like he trusted Dean to tell him when he was ready.
Dean hated how that made it harder.
Because he wanted to blurt it out. To shove the box across the table, to say, You’re everything to me. Will you marry me? But the words were stuck behind a wall of fear and doubt, and he’d spent his life building that wall brick by brick. It wasn't coming down in one dinner.
So instead, he reached for his beer again and raised it in a half-assed toast.
“To meatloaf that probably isn’t meat, and a night we’re both clearly nailing.”
Cas clinked his glass of water against the bottle without hesitation. “To barely edible food and successful emotional repression.”
Dean laughed, too loud, too grateful. “Now that’s a Winchester-Nova—wait, Novak—family motto if I’ve ever heard one.”
They both smiled, the tension easing just enough to breathe, but only just. Beneath the laughter, the boxes in their pockets waited, heavy as anchors.
Neither one of them was ready to open the floodgates.
Not yet.
But soon.
Silence fell again, thick and clumsy. Somewhere in the back, the jukebox clicked and started playing Elvis’s Can’t Help Falling in Love.
Of course it did.
Dean groaned softly and glanced at the ceiling, then back out the window beside their booth. Neon lights from the diner’s sign flashed red and white across the hood of the Impala. Outside, the parking lot was quiet, save for the occasional hiss of tires rolling past on the highway.
He had planned this. Hell, he’d been practicing what he was going to say for a week. Running lines in his head during hunts, muttering to himself in the shower like a lunatic. But now, across from Cas—his best friend, his partner, his everything—his throat felt like it was closing. His heart thudded like it wanted out of his chest.
“So, uh…” Dean cleared his throat and gestured toward the corner. “Jukebox’s got that old Zeppelin track you like. Not that Stairway crap. The good stuff.”
Cas nodded slowly, not quite meeting his eyes. “Mm. Yes. I… noticed.”
Dean’s eyebrows climbed halfway to his hairline. “You noticed? That’s it?”
Cas finally looked at him, eyes flickering with something unreadable. “You seem… distracted.”
Dean let out a sharp breath through his nose, half-laugh, half-sigh. “Yeah, well, you’re not exactly winning the Mister Relaxation award over there.”
Cas tilted his head, faintly defensive. “I’m perfectly calm.”
Dean raised an eyebrow. “Uh-huh. Right. That’s why you’ve been staring out the window for ten minutes like you’re watching for a damn omen.”
Cas shifted in his seat. “It’s… peaceful out there.”
Dean smirked. “You hate traffic.”
“I’m trying to focus on something neutral.”
“Neutral?”
Cas’s lips pressed into a thin line. “You’ve looked like you’re about to hurl since we sat down. I assumed talking about storm clouds or passing cars might be safer than whatever you’re really thinking.”
Dean blinked. Then looked down at his beer bottle, turning it slowly between his fingers.
There it was again, that thing Cas did. Saw too much. Said it too plain.
Dean’s voice came out quieter than he meant. “You always gotta go straight for the jugular, huh?”
“I’m not trying to pressure you,” Cas said gently. “But I know you. And I know when you’re not okay.”
Dean forced a crooked smile. “I’m okay.”
Cas didn’t answer, just watched him with those damn eyes that never let him squirm away completely. The silence stretched.
Dean reached for the first lifeline that came to mind.
“You hear Sam’s thinking about going back to school?” he asked abruptly. “Like, real school. Lectures and dorms and the whole deal.”
Cas blinked at the sudden pivot. “That’s… good. If that’s what he wants.”
Dean nodded too fast. “Yeah. I mean, he deserves it. Kid’s smart. Smarter than me, anyway.”
Cas tilted his head again. “Dean—”
Dean raised his bottle in a quick, deflecting toast. “To Sam, huh? Finally getting his nerdy college dreams back.”
Cas hesitated… then clinked his glass against the bottle with a soft tink. “To Sam.”
They both took long drinks, pretending it helped. Outside, a semi rumbled past, headlights sweeping across the window, briefly catching the glint of Dean’s leather jacket right where a velvet box sat hidden in his pocket, heavy and silent.
Neither of them said anything more. The jukebox changed songs. Neither of them noticed.
“So,” Cas said finally, his voice strained. “Nice weather.”
Dean looked up at him. “Cas, we fought a poltergeist in a hailstorm last week.”
“Yes,” Cas replied. “That’s what made me think of it.”
Dean exhaled slowly and leaned back in the booth, casting a glance out the window like maybe it would offer him a lifeline. The flickering neon outside painted them both in pulses of red and white, and the muted clink of silverware and murmured conversations filled the silence between them.
Cas was stirring the last of his drink with a straw like it had personally offended him. Dean had stopped picking at his food ten minutes ago, most of it still sitting there cold and untouched. Neither had said much since Elvis started crooning.
The waitress returned with her notepad in hand and a hopeful smile.
“You boys want dessert? Got fresh apple pie, chocolate cream, and some cherry I probably wouldn’t recommend.”
Dean didn’t even hesitate. “Nah, we’re good. Just the check, thanks.”
Cas blinked, startled. “No dessert?”
Dean avoided his gaze, reaching for his beer again. “Not really hungry.”
The waitress nodded and headed off, leaving the quiet behind her like a dropped curtain.
Cas was still watching him.
“You always get pie.”
Dean shrugged, still not looking at him. “Yeah, well. Not tonight.”
The air between them shifted. Something sharp flickered across Cas’s face, surprise, maybe. Or realization.
Wordlessly, he reached into the inside pocket of his coat, presumably for his wallet, but his fingers hesitated. He was clumsier than usual. Dean noticed.
More importantly, Dean noticed what slipped halfway into view.
A velvet box.
Cas saw the shift in Dean’s expression before Dean said a word, his eyes going wide, shoulders tensing, as if someone had just sucker-punched him through the ribs.
Dean didn’t blink. “What’s that?”
Cas froze, hand still inside his coat. His mouth opened like he might try to deny it, or talk his way around it. But there was nothing to say. Not really.
Cas said softly, “This is why I’ve been… strange. I was going to wait. After dessert. Or if you smiled. But I can’t do it anymore. It’s killing me.” He let out a sigh that sounded almost like defeat and slowly, silently set the small black box on the table between them.
Dean stared at it. Then stared at him. Gave a breathless, disbelieving laugh, scrubbing a hand down his face. “You’ve gotta be kidding me.”
Cas looked at Dean like a man caught in headlights. “I was going to wait.”
Dean blinked, and his hand moved on its own, reaching into his own coat and pulling out his box.
He placed it beside Cas’s.
The air between them shifted like something had finally exhaled.
Now Cas was the one blinking, his eyes flicked between the boxes, then back to Dean. “You too?”
Dean nodded, slow, dazed. “Yeah. I was gonna do it after pie.”
Cas smiled softly. “You didn’t order pie.”
Dean snorted, the tension in his shoulders finally beginning to ease. “Because I thought I was gonna puke.”
Cas’s mouth twitched. “So did I.”
They both stared at the boxes for a long moment, two small symbols of everything they hadn’t been able to say.
Then, simultaneously, they both broke into laughter, nervous, relieved, almost disbelieving laughter.
Cas shook his head. “I don’t understand. Why is this so hard?”
Dean leaned back, running a hand over his face. “Because we’re both idiots, that’s why.”
Cas tilted his head. “I don’t think that’s entirely accurate.”
Dean barked out another laugh, hollow and frustrated. “You’re telling me this is how you pictured it? Us, on a date, barely speaking, both about ready to pass out from nerves?”
Cas looked down at his plate. “No,” he said quietly. “I imagined it… differently.”
Dean’s shoulders slumped. “Yeah. Me too.”
Another beat of silence.
“I was gonna propose tonight,” Dean said, eyes wide.
“I am proposing tonight,” Cas replied, leaning in, a soft, crooked smile tugging at his lips.
“Well,” Dean said, rubbing his chin. “I guess we’re both saying yes then.”
Cas reached across the table and took Dean’s hand in his. “I suppose we are.”
Dean grinned, the tension finally breaking, all the nerves dissolving into warmth. “God, we’re idiots.”
Cas squeezed his hand. “Idiots in love.”
They opened the boxes at the same time, and there they were—two simple rings, matching in metal but chosen separately, like they’d known each other’s hearts all along.
Cas swallowed hard. “So much wasted nervousness.”
Dean shook his head, his smile soft now, real. “Nah. We cared. That’s what it was.”
“Dean.”
“Yeah?”
“Yes.”
Dean blinked. “I didn’t even ask yet.”
“You were going to.”
Dean let out a breathless laugh. “Damn right I was.”
Dean took his and slid it onto Cas’s finger. Cas followed suit, his touch reverent.
“Looks good on you,” Dean said, voice low, rough with emotion.
Cas looked up, his eyes soft. “So does forever.”
The jukebox switched songs.
They didn’t notice. They were too busy kissing across the table.