I Don’t Know How To Do This
Pairing: Dean Di Laurentis x Reader
Dean Di Laurentis had a lot of things under control.
He had his grades under control, mostly. His game was under control. His charm, his reputation, his ability to walk into any room and make people look twice at him,those were all under control too.
Feelings, however, were a completely different story.
You learned that on a Thursday night in Dean’s room, with his hand loosely linked with yours and a half-dead lamp casting gold light over the mess of clothes on the floor.
He was lying on his back, one arm behind his head, looking unfairly good for someone who had been awake since sunrise. You were sitting cross-legged beside him, tracing idle shapes against his wrist while he complained about some awful group project he’d half-carried that day.
“And then,” Dean said, staring at the ceiling like the universe had personally betrayed him, “he says to me, ‘Maybe if you contributed more, this would be easier.’”
You made a face. “You didn’t punch him?”
He turned his head to look at you, that lazy, handsome smile tugging at his mouth. “You support violence now?”
“Only in academically justified situations.”
Dean laughed softly and shifted closer, his knee brushing yours. “That is the most you thing you’ve ever said.”
You smiled, then fell quiet for a second.
Dean noticed immediately. He always did.
“Mm,” he said, clearly unconvinced. “That ‘nothing’ had a tone.”
You huffed a laugh. “You’re ridiculous.”
“And you’re avoiding the question.”
You looked down at your hands, suddenly aware of the way your pulse had quickened for no good reason. It had been building for days, maybe longer. That feeling sitting in your chest, warm and frightening, like standing too close to the edge of something you weren’t sure you were ready to jump from.
Dean reached over and nudged your knee with his. “Y/N.”
He softened a little. “Talk to me.”
The words were simple, but the way he said them made your throat tighten.
You had been together for months now, long enough for the flirty teasing to become routine, long enough for late-night movie marathons and stolen kisses and Dean showing up wherever you were just because he wanted to be there. Long enough for it to start feeling less like a thing you were doing and more like the shape of your life.
Which was probably why the truth had been sitting in your mouth for so long, impossible to swallow back down.
Dean watched you, suddenly alert.
Not silent exactly,there was the hum of the heater, the faint noise from the hallway, somebody laughing downstairs,but the space between you and Dean changed all at once. It went tight. Thin. Fragile.
His face didn’t shift much at first. That was almost worse.
You tried to breathe normally. Tried not to panic at the way his expression had gone unreadable. Tried not to regret saying it the second it left your mouth.
“Say something,” you blurted, because the quiet was unbearable. “Please.”
Dean blinked once, then sat up so fast his shoulder bumped yours. “I,”
You watched him, your heart pounding.
His mouth opened again, then closed. He dragged a hand over his face, and for the first time since you had met him, Dean Di Laurentis looked genuinely thrown.
“Oh my God,” you said, half horrified, half mortified. “Dean.”
“What?” he said, too quickly. “No, I,shit. I did not mean,”
That made you go very still.
He cursed under his breath and shoved a hand through his hair. “That came out wrong.”
You stared at him, already bracing for the blow you didn’t know was coming.
Dean looked at you once, then away, then back again, like he was trying to find the right shape for a sentence and coming up empty.
“Dean,” you said again, quieter now, “what is happening?”
He let out a breath and stood up so abruptly you nearly flinched. He paced two steps toward the window, then back again. The Dean DiLaurentis you knew was smooth, easy, confident. This Dean looked like he wanted to crawl out of his own skin.
“I’m not,” He stopped and laughed once, but it sounded wrong. “I’m not good at this.”
“At this.” He gestured between the two of you, then made another helpless motion with his hand. “Whatever this is. This whole thing where you say something that matters and I’m supposed to be normal about it.”
He saw your face and immediately swore again. “No, no, that is not what I meant.”
“It sounded a lot like what you meant.”
“Then what did you mean?”
Dean dragged both hands down his face and dropped onto the edge of the desk chair like his legs had given out. “I mean I do not know how to do this.”
That caught you off guard.
“This.” He looked at you then, and the honesty in his eyes knocked the air right out of your chest. “Being with someone like this. Real. Serious. Where there’s something to lose.”
He let out a humorless laugh, rubbing the back of his neck. “You said that, and my brain just… short-circuited.”
“Because you don’t feel it?”
“No.” The answer came too fast, too sharp.
He leaned forward, elbows on his knees, eyes locked on yours. “No. Because I do.”
Dean looked almost angry with himself now. “Yes. Obviously, yes. That’s the problem.”
Your brows pulled together. “That is not a problem.”
“It is when I have no idea what I’m supposed to do with it.”
You stared at him for a long second, processing.
He looked almost irritated, but underneath it there was something much more vulnerable, something you had never really seen from him before. Dean always had a joke ready. Always had a smirk, a line, a distraction. He could flirt his way through a conversation like breathing.
You shifted a little, still sitting on his bed, and asked softly, “You’re panicking because you love me?”
He barked out a laugh, short and disbelieving. “That sounds insane when you say it like that.”
He looked at you, really looked.
Then he said, quieter, “I’ve never done this before.”
So he kept going, as if once he started he couldn’t stop.
“I’ve never had to think this hard about somebody. About what happens next. About whether I’m screwing it up or not.” He swallowed, jaw flexing. “I’ve never had a girlfriend I actually cared about enough to be scared of losing.”
That made your chest ache.
He looked away. “And I know that sounds bad.”
“It sounds like I’m an asshole.”
“It sounds like you’re honest,” you said.
You watched him carefully. “Is this why you looked like someone hit you with a chair when I said it?”
He groaned and dropped his head into one hand. “I did not look like that.”
“You were holding my hand one second and staring at the wall like you’d been legally wounded the next.”
He lifted his head and gave you a miserable look. “I was trying to process.”
“By looking like you were about to flee the country?”
You had to bite the inside of your cheek to keep from smiling. The tension wasn’t gone, but something in his confession made it easier to breathe.
Dean saw the small shift in your face and looked immediately guilty. “You’re not mad?”
You blinked. “Should I be?”
“I made you say it and then stood there like an idiot.”
“That is one way of describing it.”
You moved closer by instinct, sliding off the bed until you were kneeling in front of him. “I’m not mad.”
Dean’s expression didn’t fully relax, but some of the tightness left his shoulders. “You’re sure?”
He studied you. “You’re really not?”
You reached for his hand and held it. “Dean, I said it because I meant it. Not because I needed you to say it back right this second.”
Something flickered across his face at that, something almost pained.
“I wanted to,” he admitted.
The words were so quiet you nearly missed them.
You stilled. “You wanted to?”
Dean looked at your joined hands. “Yeah.”
Your heart thudded once, hard.
He continued, voice rougher now. “I wanted to say it. I just,” He exhaled through his nose. “I didn’t want to get it wrong.”
The honesty in that hit you harder than anything else had.
You squeezed his hand. “There is no wrong way to say it.”
Dean’s mouth twitched faintly, but it didn’t become a smile. “That is not comforting.”
“I know. That’s why it’s not comforting.”
You laughed softly, and finally, finally, some of the tension in his face eased too.
He looked at you for a long moment, then said, “Can I tell you something?”
He took a breath. “The second you said it, I stopped being funny in my own head.”
He frowned. “Why are you making that face?”
“Because that is the saddest sentence I’ve ever heard in my life.”
Dean huffed a weak laugh. “I’m serious.”
He rubbed his thumb over your knuckles. “I just kept thinking, ‘Oh, this is real. This is the point where I’m supposed to know what I’m doing, and I don’t.’”
You softened. “Nobody knows what they’re doing.”
Dean made a face. “Garrett knows what he’s doing.”
“That is because Garrett is annoyingly competent.”
“Exactly. Logan somehow knows when to be emotionally available. Tucker has the patience of a saint. And me?” He let out a breath. “I usually just show up and make people laugh and hope nobody notices I’m improvising.”
You stared at him for a second, then said, “I noticed.”
His eyebrows lifted. “You did?”
The question was so quiet it almost broke your heart.
You reached up and touched his cheek. “Dean, I stayed because it was you.”
His eyes closed for just a second.
When they opened again, they were softer. Less guarded. Less panicked.
He swallowed. “Okay. I’m trying.”
Your chest felt too full all of a sudden. “That’s all I need.”
Dean leaned forward until his forehead rested against yours. “You are very calm about this for someone who just dropped the emotional equivalent of a grenade.”
You laughed, breath warm against his mouth. “I was not calm.”
He nodded slowly. “Fair.”
There was a beat of silence, but it wasn’t the bad kind anymore.
Then Dean said, “I love you too.”
He immediately winced. “Too dramatic?”
You stared at him, barely believing what you’d heard.
His face turned a little pink, which was both incredibly unfair and deeply endearing. “I said it wrong, didn’t I?”
You shook your head so fast it almost made you dizzy. “No.”
He searched your face, still clearly nervous. “You’re sure?”
You laughed, watery and disbelieving all at once. “Dean.”
He looked embarrassed now, which somehow made him more Dean than anything else. “I’m trying to be sincere here.”
“And I’m very aware I’m not doing it with my usual level of smoothness.”
“That is because you’re adorable when you’re scared.”
His eyes widened. “Do not call me adorable.”
He gave you a look, then reached out and pulled you into his lap in one quick motion. You squeaked in surprise, then immediately dissolved into laughter as his arms locked around your waist.
Dean buried his face briefly against your shoulder. “This is your fault.”
“Yes. For making me feel things.”
You tilted your head back to look at him. “I thought you just said you loved me.”
He lifted his head slowly, eyes warm now, a little shy, and much more certain than before. “Yeah,” he said. “I did.”
The words sat between you differently this time. Less like a cliff edge. More like a hand held out in the dark.
You smiled, and this time it stayed.
Dean stared at you for a second, then sighed dramatically and dropped his forehead to yours again. “God, I hate how much I like this.”
You grinned. “Like what?”
“This.” He gestured vaguely at both of you, then kissed the corner of your mouth. “The feelings. The vulnerability. The complete loss of control.”
You laughed softly and wrapped your arms around his neck. “You’re such a drama queen.”
Dean’s expression changed immediately, his eyes sharpening with concern. “That was a joke.”
You smiled against him. “I know.”
His shoulders dropped a fraction. “Okay.”
Then you kissed him first, slow and sure, and Dean kissed you back like he had been holding his breath for weeks and finally remembered how to exhale.
When you pulled away, he kept one hand at the back of your neck and looked at you like you were something rare and impossible.
“I’m still going to be awkward about this,” he warned.
You brushed your nose against his. “I know.”
He exhaled a laugh, then kissed you once more, softer this time. “Good,” he murmured. “Because I’m pretty sure I’m in too deep now.”
You smiled, resting your forehead against his.
“Yeah,” you whispered. “Me too.”
