Figuring It Out @stitchintimefan - Tumblr Blog

My Happy Ending

Dean Winchester x Reader

Summary: I told myself it didn’t matter. That Dean flirting with someone else wasn’t a big deal—not this time. But the truth? It broke something, I wasn’t sure if I was ready to walk away… or if he’d even notice if I did. But something was going to give—either my heart, or the silence between us.

🍎🥧❤️🍎🥧❤️🍎🥧❤️🍎🥧❤️🍎🥧❤️🍎🥧❤️🍎🥧

I was becoming tired of it. Watching Dean flirt with the busty diner waitress was making me sick. Seeing the way she completely folded over the table, the minute Dean mentioned her name made me want to jump over the table and straight for the door. But I knew that was kinda dramatic (but at this point, what did it matter?).

Sam watched me across the table as he sipped on his black coffee. Sam was always observant, maybe a little too much at times. But the way Sam looked at me right now, as if he was trying not to look my way, made the tears I tried so desperately to hide much harder.

Daisy was her name. Ugh, what an eye roll, I swear if she told the story to Dean again about how people called her Daisy because she had a touch as light as a feather, and her mother said she reminded her of a sunny day I'd barf. But who was I kidding? Maybe I was easedropping a little too much, but how could I help it when her agonizing laugh lingered longer with every word.

The two were standing too close to each other for my liking, at least. Dean's arm rested against the counter as he oogled at the apple pie (and probably the open buttons of "Daisys" blouse). I'm surprised my vision was crystal clear at the moment. Seeing as a few days ago, I could barely see a sign across the street.

I pushed my plate away. The eggs I had once enjoyed had now gone cold—like everything else in this heartbreaking diner. Dean was still standing at the counter, grin wide from ear to ear, a smile I thought was only reserved for me. Letting Daisy’s syrupy voice fill his ears, she twirled a piece of her hair and leaned a little too close.

I suddenly couldn’t take it anymore, everything became too much.

"I’m gonna get some air," I muttered, my voice barely audible as I stood from the booth. I smoothed my hands over the navy shirt I had chosen to wear only because Dean said it was his favorite color on me, but who was I kidding? Was that another gimic, too?

Sam looked up from his coffee, brows knitting with concern. "Y/N—"

But I didn't bother to hear the rest. I was already gone.

The door swung closed behind me with the sound of a loving chime I might’ve once found charming. But now all that's left is just another reminder of what I wasn’t—a girl worth staying at the table for.

I leaned against the Impala. It was cool beneath my palms, steady, reliable. Everything Dean wasn't.

For a moment, I just stood there, breathing in the morning summer air like it could wash the ache away. But it stayed, only growing worse as it poked right under my ribs. Leaving a constant reminder of everything that I tried to hide.

I heard footsteps but I couldn't turn around. I almost expected it to be Dean, but it wasn't.

"You okay?" Sam asked, coming to stand beside me. He didn't crowd me. Just stood in front of me, blocking whatever sunlight was facing my way. Sam always stood taller than most, but hell, I could remember a time when we were both the same height. I'd never think there'd come a time when Sam Winchester would be comforting me, but now it seems that anything was possible.

"No," I said finally. "But I will be."

Sam nodded tenderly like he already knew. The sun grew brighter behind him, projecting a summer glow to his appearance. I longed to feel the heat of the sunshine in some way to sorta wake me up from this mess, but right now, everything felt cold.

"You don’t have to keep pretending you’re fine Y/N. You’re allowed to not be okay with the way he looks at other girls. How he treats them when your around."

I let the silence stretch between us. Sam’s words weren’t cruel. They were honest. That’s what made them sting.

"I thought he was different," I said. "With me at least."

Sam’s voice was soft. "Maybe he is. But he’s still Dean. And Dean... he doesn’t always know how to deal with what scares him."

"And I scare him?" I scoffed, rolling my eyes. It was pathetic really.

"Yes, of couse you do Y/N," Sam placed a hand across his face in a testing matter, taking a deep breath out. "Because you matter."

Just then, the door opened again, and I turned my head before I could stop myself.

There he was in all his glory, before I knew it my eyes were placed right on his before I could turn away

Dean glanced between Sam and I, frown already forming on his face. Fixing the collar of his jacket Dean starts coming our way. "What’s going on?"

I straightened my back, throwing my hair behind my shoulder. Everything was fine, I was just being dramatic. At least that's what I had to tell myself in order from losing it all. My hands were clenched as I slowly placed them down by my sides. "Nothing. I'm just clearing my head."

Dean’s sighs taking a step closer as he tears his eyes away from Sam and fully onto me now. "Y/N-"

"No," I cut him off. "Don’t do that. Don’t say my name like"

Sam gives me a silent nod before slowly slipping inside, making that stupid chime go off once again. It was just the two of us now.

Dean shoves his hands in his jacket pockets, squinting at the sun made it's way closer. Turning around, he waits until Sam is fully inside the diner to speak. "What the hell is going on with you?"

"Me! You mean besides watching you flirt your way through every woman with a name tag?" I snapped, well I wasnt expecting that to come out. "Or maybe you’re wondering why I’m not just sitting quietly and pretending it doesn’t feel like being gutted every time you look at someone else like they’re the only person in the room."

Dean eyes widen, he looked stunned. Like I’d just hauled off and punched him right in the gut. He was quiet for a moment, a moment too long because after awhile I began to walk away. But before I could make a move Dean lighty grabbed my wrist pulling me right next time him. Right smack in front of him so that his attention wasn't on anything except me.

"Sunshine I wasn’t—"

"Yes, you were-." My voice cracked for a second, and it felt like couldnt breathe. How was I supposed to tell the boy I've known since I was a teenager I was in love with him "-you were. And maybe that’s fine. Maybe that’s who you are. But I can’t keep waiting for you to notice that this is something more. I don't want to be a backup Dean".

He took a step toward me, but I didn’t move. His eyes widen in a way he didnt realize and for a moment I almost wanted to step close, but I never did. "Y/N..I never meant to hurt you," he said quietly.

"But you did," I whispered my eyes teared and I knew I had to look away. "Over and over. And maybe that's the worst part—how easy it is for you to pretend like it doesn't matter."

The wind blew through the parking lot, and Dean still didn’t say a thing. I waited for a response watching for any emotion in those big green eyes I had once loved, but nothing changed.

So I turned. I started walking.

For the first time in 10 years I walked away, and this time Dean didn't follow

---

I didn’t get that far. Just down the street, besides I knew that Sam would panic the minute Dean told him I walked away.

For a moment I didn't realize how far I walked. I had pasted the places I was excited to vist as we drove into the town, but now that all seemed like a far fetched idea. The distance between the two of us was good. I needed a moment to reflect on my thought.

I found myself at a cozy Cafe, a totally difrent vibe from the so called "diner" I had ate at moments ago. There was no agonizing bell, or overly flirty waitress at the counter. The Cafe was tiny and charming everything I so desperately seeked in a moment like this.

After ordering myself a latte, I stepped outside finding comfort in the outdoor seating. The hot drink kept me warm as the sun slowly started to set.

I didn’t expect to hear the familiar growl of bootsteps on rocky pavement.

But neverless there they were.

“Y/N—” His voice was rough, not as confident as he normally was. Like if he wasn’t sure if he deserved to say my name or not right now.

I didn’t turn around, just kept my back faced to his body as I sipped on my comfort drink. Sighing I rubbed my eyes (trying to hide myself from the fact that I could cry at any given moment). “You should be inside. Your pie’s probably getting cold.”

He didn’t laugh. Didn’t try to put on a smile.

“I didn’t mean to make you feel like you were... ” he said.

“Yeah, well, you didn’t try very hard to make me feel like I was anything at all.” I finally turned to face him. His eyes—green, full of a thousand apologies he didn’t know how to say—met mine. I didnt know what to think as I looked at those eyes, and the memories they held.

“I flirt,” he said an octive higher. Dean opens his arms in a wide stance like he was confessing a sin to the sky. “I joke, and you know why I do it because I push people away because it’s easier than getting hurt.”

"And what about me?" I asked, leaving my coffee on the wooden table I begin to stand up. "What do I get to be in that equation? The girl who keeps forgiving you while you hand pieces of yourself to strangers?"

“No,” he said quickly. Dean sighs running a hand through his hair as he tilts his head to the sky once again. His eyes meet mine for a moment again before he begins to speak in a only a whisper him and I could hear.. “You’re not just anyone Y/N. You never were.”

I stared at him, waiting—for once—for more than just words. For something real.

Dean stepped closer, slow, deliberate. “You know what, you scare the hell out of me,” he admitted, pointing a finger in my way. “Because when I’m with you, I feel like I’m not just surviving anymore. I feel like... maybe I could have something good. Something real. And I’ve never let myself have that. Not once.”

He paused, breathing hard like the words were heavier than he meant them to be. “But I can’t do this halfway anymore. I won’t.”

My eyes squint, head tilting in confusion as my heart hammered against my ribs, but Dean was still here and he didn't stop.

“I love you.” The words dropped like thunder between us. “I’ve loved you longer than I’ve had the guts to say it. And I’ve messed it up, I know that. But I swear to God, Y/N, you’re the only thing that feels right. The only thing I want.”

I froze.

Not because I didn’t feel the same—but because I’d waited so long to hear those words, I wasn’t sure they were real.

“You... you love me?” I asked, almost breathless. The air was cold and my brain was foggier then before. Dean Winchester loves me? Dean Winchester loves me!

Dean gives a small, lopsided smile—uncertain, but hopeful. Tilting his head down towards mine he faces his eyes against mine. “Yeah. I do. It’s always been you.”

I just stared at him, all the anger and heartbreak dissolving under the weight of his confession. My voice caught in my throat. I wasn’t ready for that—not the way he said it. Not with that soft, wrecked look in his eyes that made it impossible to doubt him.

“I—Dean, I don’t even know what to say,” I whispered.

He chuckled nervously, a cheesy grin forming on his lips. "Kinda hoping you'd say something like... you love me back. Or maybe just kiss me before, you know I pass out from panic".

A slow smile tugged at my lips as I stepped into his space, fingers reaching up to brush the side of his jaw.

“You’re such an idiot,” I said, voice cracking with emotion. “But yeah... I love you too. You absolute mess of a man.”

He exhaled like I’d just brought him back to life. Leaning his head against mine he stared into my eyes. Never in my life did I think I'd be standing with Dean Winchester eye to eye. But there I was.

Slipping my hands around his neck, I kissed Dean—finally— and for once in my life it finally sememed like everything was going my way.

The kiss wasn’t rushed. It wasn’t desperate or messy or built on everything we’d been running from. It was slow, deliberate—like he needed to memorize the feel of me, like he didn’t want to mess it up now that I was finally his.

When we pulled apart, his forehead rested against mine, breath warm between us.

“God,” he murmured, “you have no idea how long I’ve wanted to do that.”

I smiled, fingers still curled into the lapel of his jacket. “Well, for the record, you’re a pretty good kisser for someone who’s been too busy ignoring his feelings.”

He chuckled, the sound low and genuine, and for a second it was music to my ears. “You bring it out of me, sweetheart.”

He tugged me into a hug, arms wrapping around me like he finally realized how easily I could’ve slipped through his fingers—and how he had no intention of letting me go again.

We slowly made our way back at the motel, Sam was sat at the the kitchen table with a grin that said it all. Dean and I walked, coffee and pastries in our hand. We joined Sam at the table eating and drinking in silence, we didn’t talk much. We didn’t need to.

Later on that night Dean tossed me one of his flannels—soft, warm, and cologne that smelled just like him. Sam was asleep on bed next falling asleep mere hours ago. Dean lowers the TV before making his way over to me, and just like that, I was wrapped in him, in the warmth he only ever showed when he let his walls down.

We curled up on the bed together, his arm around my waist, fingers tracing lazy circles on my hip. The TV was on, but neither of us was listening. Pressing a kiss to my temple he begins to whisper, “You know, this... this could be our new normal.”

Staring up at him I glint “Are you suggesting snuggling in cheap motels after every hunt??” I teased.

Grinning against my skin, he presses a kiss to my ear. “Exactly that.”

For once, there were no secrets. No half-truths. Just me and Dean. And the soft, steady rhythm of something that felt a hell of a lot like forever.

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