Info: Dean never thought he’d be the man to settle down. But y/n (and Sam) changed all that.
Relationship: Dean Winchester x reader
warning: brief mention of death of parent
Dean and y/n had met during a case. Y/n’s father had been taken, and later killed, by a wendigo, not that y/n had been aware of what that was, and Sam and Dean had came by to check it out. Living on her own, y/n was hesitant to allow the two men into her house, but when Dean flashed his smile, y/n grew fond of them. During their research, the brothers seen a pattern on who the wendigo were going for, and y/n matched it. Dean felt protective of the woman he just met, and decided to warn her, but they’d been too late. Dean still remembered the teasing Sam had given them during the hunt to find the wendigo and it’s victims. They had found them under an old tree that had an opening, and y/n had been the one to make first contact with Dean when he cut her down. Pulling him into a hug, she looked at him before kissing him on the cheek.
“Dad’s dead.” y/n spoke, looking at a body that lay on the ground.
“I’m sorry y/n.” Dean spoke, placing a hand on her shoulder.
“He wasn’t the best dad but, he was all I had left of family.” Y/n spoke, tears building in her eyes before she dug her head in Dean’s shoulder.
‘What I do’ Dean mouthed at his brother as he stood still.
‘Comfort her’ Sam mouthed bag, gesturing a hug.
Dean wrapped his arms around y/n’s figure, patting her back before tightening his grip on her. He remembered her sniffles before pulling away, apologizing for being such a mess. The brothers had led y/n away from the scene before calling the cops, the lads telling the story of a ‘bear’ attack while y/n curled in on herself as she was checked over. For some reason Dean felt compelled to stay for the funeral, much to the surprise of Sam, which was small and only really included y/n and some friends of his dad. There was only the two of them, so y/n opted to get him cremated, avoiding all the trouble of burying him.
“I can’t stay here.” y/n spoke as she stood outside the church with the brothers.
“Come with us.” Sam spoke quickly, causing Dean to whip his head to him.
“Sam, are you crazy?” Dean snapped.
“We would love the company.” Sam replied, eyeing Dean as he spoke.
“Really? You’d want me, someone you barely know, join you guys?” Y/n spoke, unsure of what to say.
“Ah how bad can it be?”
“I don’t think y/n would like the living on the road lifestyle Sammy.” Dean stated.
“Actually, I’d love to.” Y/n smiled.
“Really?” Both brothers spoke, shocked at the answer.
“I always wanted to travel.” Y/n shrugged before walking away from the brothers.
“Sammy I swear..”
“You'll thank me later.” Sam smirked before jogging to catch up with y/n.
--
The next few months had been some of the most scary yet thrilling times of y/n’s life. Majority of her time was spent in a motel room while Dean and Sammy went on cases, but each night was spent with Dean at the bar, a beer in hand. Every morning she would go on a run with Sammy, and after she’d grab them some breakfast. She had managed to convince Dean to train her with their weapons, and had even begun to do research with them. Dean had grown fond of the girl that stayed with them, and during the rides Sam would feel like a third wheel with the conversations Dean and y/n would have. He would often but in with some sarcastic remark, and y/n would just go red while Dean would make a snarky reply. But it was no lie that the two had grown close.
Soon the two bedrooms turned to one, and y/n would often wind up in the same bed as Dean. The only time they didn’t was when an argument had entailed, which was very rare. Neither one of them made a move until Sam had cornered Dean one morning while y/n was out grabbing some breakfast.
Y/n remained at the door, staring at Dean as he refused to make eye contact. The room was silent, until y/n cleared her throat, moving to place the food on the table. Dean moved his head to watch her, before sighing and standing up from the bed, moving towards her.
“You know you like her?” Sam stated, once the door closed behind them.
“I don’t know what your talking about.” Dean stated, sitting on his bed.
“You know exactly what I’m on about. You like her, she likes you. Make a move already.”
“No.”
“Why not?”
“Because Sam, you know me. I’ll fuck it over somehow.” Dean stated, throwing his arms out.
“No you won’t Dean, I’ve seen the way you look at her. Ever since she’s joined us you haven’t even looked at another woman, and that’s saying something for you.” Sam stated, his explanation making Dean raise an eye brow at him.
“Yeah well, I’m sure she don’t like me that way.”
“Are you blind?” Sam asked, laughing at his brother, “She idolizes you Dean. Out of both of us she goes out with you most nights to the bar, she asked you to teach her our world, hell she sleeps in your bed.”
“So, what. That means nothing.” Dean tried to deny.
“You and I both know your just making excuses. Your crazy for her Dean, just admit it.” Sam stated, and Dean looked down.
“You like me?” A voice spoke from the door, causing both brothers to look up in shock.
“Damn it Sam.” Dean sighed, rubbing a hand down his face.
“I’m not sorry.” Sam muttered to him, patting him on the shoulder before walking to y/n. “Thanks for breakfast y/n. I think I’ll eat outside today.” Sam smiled, grabbing his food from the girl before leaving the room.
Dean looked into y/n’s eyes, trying to read her. Seeing his weariness, y/n rolled her eyes and decided to close the gap, bringing her lips to his. Feeling her lips, Dean froze but quickly eased into it, grabbing her hips as their lips moved together. It was short and sweet, and y/n quickly pulled away from him, kissing his cheek.
“Y/n, I’m sorry that I like you.” Dean stated, standing behind her.
“Why are you sorry?” Y/n asked, turning around to face him.
“I don’t know, because you clearly don’t like me and..”
“Why says I don’t like you?” Y/n stated, scrunching her eyes in confusion.
“What?” Dean asked, generally confused.
“Your not one to say sorry, so don’t be. And your also not one to care what others think so don’t. I like you Dean, because of who you are.” Y/n stated, moving closer to Dean.
“My lifestyle..”
“OUR lifestyle isn’t perfect, but it’s ours. And I’m glad I joined you guys.” Y/n stated, placing her hands on Deans shoulders as she came closer.
“Let’s see how this goes. What’s the worse that can happen?” Y/n stated.
Dean just smirked before giving y/n a kiss before guiding her back towards the table. He reached behind her before pulling away from her, and y/n smirked when he seen him with his breakfast burrito. He just smirked back before taking a bite, causing y/n to roll her eyes.
---
That was three years ago, and since than their relationship had blossomed, Dean and y/n became closer than ever, and Dean grew protective of his girl when she started doing cases with them. Of course she was a natural, and Dean didn’t have to worry about much, and would smirk when he got to watch her fight for herself. The only time Dean had to save her was when Lucifer had taken her as leverage against the Winchester brothers. That was two years into their relationship, and had scared Dean enough that he knew what he had to do. It was how he ended up asking her to marry him.
Their relationship wasn’t one people would call a realistic relationship. Dean and y/n never done the whole ‘will you be my girlfriend/ boyfriend’ question. They never done anniversaries, they just knew they were together and that was that. So when asking her to marry her, that was no different. There was no engagement ring, he didn’t even get down on one knee. He just ran to her and pulled her into a kiss saying ‘that’s it, we’re getting married babe’ which had caused Sam to chuckle at his antics. But y/n didn’t care, she wasn’t one for flashy, and let’s be realistic, their lifestyle wouldn’t allow for it.
Even their ‘ceremony’ was short. The two went to get the marriage license, and once they had that Dean called Cas, who officiated the wedding for them. They didn’t even have wedding bands, until Sam showed up one day and handed Dean a box.
“What’s this?” Dean asked, looking at the box that was placed in his hand.
“Maybe open it.” Sam mused
“What is this?” Dean asked his brother as y/n came out from the bathroom, drying her hair with a towel from her shower.
“They’re rings Dean. Come on, must I do everything for this relationship that isn’t even mine.” Sam sighed.
“Sam, you didn’t have to.” Y/n gasped, looking at the rings in the box.
“Well I figured you may as well have at least the wedding band to show your with this idiot.” Sam mused, pointing at Dean.
“Hey.” Dean stated ,insulted.
“Your so sweet Sam, I don’t know what we’d do without you.” Y/n smiled, moving to kiss her brother in law on the cheek.
“Probably never be together and die alone.” Sam shrugged, causing y/n to swat at him as Dean shouted at him again.
“Well go on, may as well put them on together.” Sam indicated, sighing as he dragged y/n to stand in front of Dean.
“Y/n Winchester, the love of my life.” Dean smirked, taking the smaller silver ring, which had D & y/initial engraved on it, and sliding it on y/n’s ring finger.
“Dean Winchester, my one and only.” Y/n smiled, doing the same with the larger ring before Dean cupped her cheek and pulled her in for a kiss.