Pairing: Dean Di Laurentis x Reader
Dean Di Laurentis had been planning this date for two weeks.
That was already suspicious.
Dean did not plan anything unless someone forced him to or he wanted to make a point. So when he showed up at your apartment in a dark button-down and a jacket that made him look unfairly good, you knew immediately that something was happening.
You opened the door and stared at him. “Why are you dressed like that?”
Dean smiled, very pleased with himself. “Hello to you too.”
You crossed your arms. “Dean.”
He leaned in and kissed your cheek before stepping back. “Get dressed.”
You frowned. “That is not an explanation.”
You hated that he won that stare-down almost immediately.
“Fine,” you muttered. “But if this is another one of your stupid ideas, I’m making you suffer.”
Dean grinned. “That’s the spirit.”
You changed into the nicest thing you owned while he sat in your living room pretending to be patient and failing because he kept checking his phone like he was nervous.
That alone should have warned you.
When he finally got you outside, he opened the car door for you with exaggerated charm and said, “Ready?”
You squinted at him. “Why do you look like you’re about to ask me a question?”
The restaurant he drove you to was not the kind of place you usually went to with Dean. Not because he didn’t like nice things, but because the two of you were usually much more chaotic than formal. This place had candlelight, white tablecloths, and actual jazz playing softly in the background.
You stopped just outside the door and looked at him. “Dean.”
He raised a brow. “You don’t like it?”
You searched his face for a joke. “Why are we here?”
Dean’s mouth curved, but there was something softer behind it now. “Because I wanted to take you somewhere nice.”
He held your gaze for a second, then added, “And because you keep pretending you don’t deserve nice things.”
That caught you completely off guard.
The words hit a little harder than they should have. Not because they were dramatic. Because he said them so matter-of-factly, like it was obvious.
You looked down for a second before he held out his hand.
“Come on,” he said. “You’re making me nervous.”
You laughed softly and took it.
The evening started perfectly.
Which, in hindsight, was the first sign it was doomed.
Dean was charming in a way that made the waiter smile, you smile, and the older couple at the next table smile like they were watching a movie. He pulled your chair out. He ordered wine without pretending to know more than he did. He listened to you when you talked, really listened, like every detail mattered.
You were beginning to relax.
That was when the first disaster happened.
The candle on the table tipped.
Not dramatically, not dangerously, but enough that Dean’s hand shot out too fast and knocked over the water glass instead. It crashed to the floor with a very loud shatter.
The entire restaurant went silent.
He looked at the broken glass, then at the waiter, then at you.
And then, because he was Dean, he did the worst possible thing.
It started as a single helpless breath, then got worse when he realized how absurd the whole thing looked. You covered your mouth, trying very hard not to join him, but once you saw the waiter’s expression shift from alarm to patient resignation, you lost it too.
The waiter, clearly used to this kind of thing, came over with a fresh napkin and said, “It’s all right.”
Dean looked horrified and apologized three times in a row.
You were still laughing when the second disaster hit.
Dean reached for it at the exact moment you did, and because neither of you was paying attention anymore, the basket tipped over into his lap. Several rolls rolled onto the floor. One hit the leg of the neighboring table. Somebody gasped.
You both stared at it for one second before Dean leaned back in his chair and said, in complete deadpan, “I have no idea how this happened.”
That was enough to make you snort so hard you nearly choked on your water.
By the time the entrée arrived, both of you were already laughing too much to pretend this date was going to go smoothly.
And then the candle on the next table flickered too close to Dean’s sleeve.
He jerked his arm back too quickly, caught the edge of the wine glass with his wrist, and sent half of his drink over the table.
Then he put both hands over his face and muttered, “I cannot believe this.”
That made you laugh so hard you had to set your head on the table for a second.
When you finally looked back up, Dean was staring at you with the kind of fond, helpless expression that made all the disasters suddenly feel worth it.
“What?” you asked, still smiling.
He shook his head. “You’re beautiful when you’re laughing.”
Your face warmed instantly.
“Don’t say that after you just destroyed half the restaurant.”
He looked unbothered. “I’m serious.”
You looked at him for a second, then smiled because there was no good reason not to.
The rest of the night was a disaster in smaller, funnier ways.
Dean spilled a little sauce on his cuff and tried to hide it.
You dropped your napkin and he picked it up only to knock his fork under the table.
The waiter returned three times with increasingly polite concern.
At one point Dean tried to help you cut your food and somehow managed to shoot a piece of bread halfway across the room.
You were laughing so much your stomach hurt.
By dessert, the two of you were openly making jokes about the candlelight, the broken glass, and the fact that Dean now had a bread-related criminal record.
When the check came, you looked at him and said, “So this was your big romantic plan?”
Dean leaned back in his chair and smiled like he had finally accepted defeat. “Yeah.”
You grinned. “You’re not very good at fancy.”
He shrugged. “I’m great at you.”
Dean’s expression softened when he saw it. He reached across the table and took your hand, thumb brushing once over your knuckles.
“I wanted to do something special,” he said quietly. “I know we’re usually a mess. I just thought maybe tonight could be different.”
“You think this wasn’t special?” you asked.
He looked around the wreck of the table, the bread on the floor, the candle wax on his sleeve, and then back at you.
He smiled. “It was special because it was with you.”
You squeezed his hand and laughed a little because he was too good at saying things that hit you right in the chest when you were least prepared for them.
By the time you got back to the car, you were still smiling.
Dean turned to you before starting the engine. “Okay. Be honest.”
You looked at him. “About what?”
Then laughed. “Dean, no.”
He looked relieved immediately.
You leaned over and kissed the corner of his mouth. “It was ridiculous.”
His mouth curved. “Yeah.”
“But it was still you trying to make me feel special.”
Then he smiled, a little shy under all the chaos, and rested his hand over yours on the console.
“Mission accomplished?” he asked.
You looked at him and felt all the frustration and embarrassment and laughter from the night settle into something warm and sweet.
“Yeah,” you said softly. “Mission accomplished.”
He looked absurdly pleased with that answer, then finally started the car.
And because this was Dean, and because he could turn even a disastrous dinner into something memorable, he reached for your hand again before pulling out of the parking lot.
You laughed under your breath, and he smiled to himself like the whole mess had gone exactly the way he’d hoped.
