Chapter Text
Thanksgiving Day
Y/N’S POV
You watched in disinterest as your brother got down on one knee and proposed to his girlfriend (of six months) in your family’s living room. Not that you weren’t happy for him, finding love or whatever, but this just meant the next few holidays were going to be absolute hell for you. Everyone in your family was now pretty much married, engaged, or dating. Everyone except you, which sucked extra hard because you were a girl and you were the oldest, which just meant a constant stream of questions like, “Y/N, when are you getting married?” or “Y/N, have you tried this dating app?” or “Y/N, have you found ‘the one’ yet?”. You stifled a scoff. “The one”. What a fucking joke. You tried your best to plaster on a fake smile and pretend to be happy for your little brother, although, besides being bitter about your own mess of a love life, he had only known the girl six months and you didn’t think that it was a good idea all-around. And Thanksgiving? Why’d he had to do it at Thanksgiving? You couldn’t name a more un-romantic holiday.
“Congrats, you’ve beat me to it,” you smiled, as you gave your brother a hug. He just laughed and hugged the next person down the line of family members waiting to congratulate him. You rolled your eyes at the unnecessary commotion and made your way into the kitchen to check on the turkey. At least that was the one good thing left about this holiday: the food.
“So, Y/N,” your aunt began once everyone was sat at the table, about halfway through the meal, “do you have a special someone?”
Dear God, I’d going to murder someone before the night is over, you thought to yourself before putting on what was probably the 50th fake smile of the night and replying, “I don’t.” Your aunt looked at you with sympathy and you hated it. As if you needed sympathy for not having a boyfriend. As if you were just a miserable little hag without a man at your side. It made you want to barf, but you just settled for playing with the mashed potatoes on your plate.
Christmas Day
DEAN’S POV
“You’re sure they know I’m coming? This is our second date, I feel like it’s kinda comin’ on a little strong,” Dean said, as he followed his date up the driveway of her house. He had no clue what he was doing there; he had only been on one other date with this girl and it wasn’t even all that good. But it was Christmas, and his brother was off with his girlfriend somewhere, and he was going to be alone otherwise. So, when Ella invited him over for Christmas dinner, he thought, “why not?”. Now, he was second guessing his decision and praying that they weren’t expecting him to have brought any gifts. Again, this was the second date. He barely knew the girl.
“Yes, and they’re so excited to meet you! I’m so glad you could make it!” Ella chirped, as she rang the doorbell.
Jesus Christ, I’m going to kill myself, Dean thought to himself as Ella’s overly-excited tone rang in his ears. She hadn’t even acknowledged his whole “coming on strong” statement, and that’s when he realized that the chances of this night ending well were slim to none. After two dates, she was bringing him home to meet the parents. Why did he ever agree to this? What the hell was he thinking?
“El-bell!” Ella’s mother exclaimed as the front door opened, pulling her into a tight hug. Dean held back his desire to physically cringe at the Christmas sweater her mom was wearing, only to see that her dad was wearing a matching one as the door opened wider. Now he wanted to throw up. God, they were those people. “And you must be Dean!” Ella’s mom said with a smile as she ushered Dean over the threshold and into the house, pulling him into a tight hug. Yeah, there was no escaping this hell now.
“Yes, ma’am,” Dean replied, trying his best to make his smile look genuine.
“I’m Angie, this is Bill,” Ella’s mom beamed, pointing to her husband who offered his hand to Dean with an oddly cheery smile on his face. Dean shook it and nodded a ‘hello’. “We’re so excited to finally meet you, Dean. Ella’s just told us oodles about you!”
“Oh, has she? This is only our second date,” Dean chuckled nervously, scratching the back of his head as he glanced over at Ella with a curious look on his face.
“Oh, well, yes, but… when you know you know,” Angie beamed, clearly totally oblivious to Dean’s discomfort. Son of a bitch. I’ve found the fucking loony bin, Dean thought to himself. At least he had figured out that Ella wasn’t the one on the second date, and not a year in. “C’mon, Bill is going to finish up on the dinner and I can show you El’s baby pictures!”
Oh, God, no. Please don’t, is what Dean wanted to say. But he settled on, “can’t wait!”, as he followed Angie into to the living room and was sat in between her and her daughter in no time, a photo album in his lap. It was going to be a long fucking night.
Someday Between Christmas and New Year’s Eve
Y/N’S POV
You sighed as you made your way through the crowded mall. You were shopping for a dress for some stupid New Year’s Eve party that you had been invited to, but you weren’t even sure that you were going to go yet. For one, you didn’t have a date, and you didn’t particularly want to be surrounded by kissing couples when the clock struck 12. Secondly, you’ve had it up to your ears with holidays. As if Thanksgiving wasn’t bad enough, Christmas was even worse. Your family insisted on wearing matching Christmas sweaters – barf – and your mother tried to set you up with the next-door neighbor who had just moved in – double barf.
“But Y/N, he’s a doctor,” your mom’s voice echoed in your head.
“But mom, I don’t care,” you had replied.
You turned the corner, spotted the pretzel stand, and began making your way towards it. You needed a snack to get your mind off of how irritated you were with the holidays, because Lord knows if you didn’t show up at that damn New Year’s Eve party, the line of questioning about your love life would extend to be not only from your family, but from your friends as well.
“Hi, can I just get one cinnamon-sugar pretzel please. And an iced coffee,” you asked the woman working at the pretzel stand, who looked like she absolutely hated her job as she nodded and began to fill your order. You understood her mood. If you worked at a pretzel stand in the middle of the mall in the middle of the holiday season, you’d hate your life too. More than you already did. You thanked the woman as she handed you your order and offered her a smile, to which she did not return, not that you minded. You respected her honesty. You spun around on your heels to leave, pretzel in one hand and iced coffee in another, when it happened. You know, that thing that happens in every cheesy Hallmark Christmas movie ever. Because, admittedly, you weren’t exactly watching where you were going, you collided with a random stranger’s chest, iced coffee went everywhere, soaking through your shirt and his, your pretzel fell to the floor, and the whole mall seemed to stop in their tracks for a split second to watch the shit show happen. “Oh my God, I am so sorry,” you blurted out, looking at his coffee-soaked tee.
“Son of a bitch,” he mumbled as he looked down at his shirt. “Don’t worry about it, it happens,” he said, although you could tell by the tone of his voice that he was irritated. Who wouldn’t be? You looked from his shirt to his face, and the air almost left your lungs as you laid your eyes on him. Undoubtedly, he was the most gorgeous man you’d ever seen. This would happen to you. Just your luck.
“No, no, let me buy you a new shirt or something,” you offered, picking your pretzel up off the ground and throwing it in the nearest trashcan.
“Me a new shirt? I think you might want to take care of your shirt first,” he smirked. Your eyes went wide when you realized what he was referring to. You were wearing a light blue shirt, and since it was just the mall, you decided to forego the bra today. Your hands instantly folded across your chest to keep a shred of your dignity. The man chuckled. “Here,” he said, shrugging off his plaid over shirt and handing it to you. Somehow, the coffee had avoided most of the button-down and concentrated on his t-shirt underneath.
You smiled sheepishly and took the plaid from him, quickly putting it on and buttoning it up. “Thanks,” you replied, offering your hand out to him. “Um, I’m Y/N.” He shook it firmly.
“Dean,” he smiled, before glancing over to the pretzel stand and announcing that he was going to get some napkins to clean up the coffee from the floor. You watched him as he asked the woman who hated her life for some napkins and she handed them to him begrudgingly before going back to the register. You and Dean fell to your knees and began sopping up the coffee with the pile of napkins to the best of your ability. After about five trips from each of you to the nearby trashcan to dispose of the soggy napkins, the floor may have been sticky with coffee residue, but it wasn’t a slipping hazard anymore.
“Thanks, you didn’t have to help. That was my bad,” you said shyly, hugging yourself out of embarrassment from the whole situation.
“No, no, it’s fine. Honestly, I shouldn’t have been surprised that it happened to me considering how my holiday season’s been goin’,” Dean chuckled as you both started to make your way away from the scene of the mess. You were heading towards the nearest clothing store so you could buy Dean a new shirt, but you had a feeling he’d protest so you kept the conversation going so he wouldn’t notice where the two of you were headed.
“You too, huh?” You laughed breathily, flashbacks of your own holidays playing through your head.
“You mean to tell me I’m not the only one who had a shit Christmas?” He asked, his eyebrows raised in surprise.
“Shit Christmas, shit Thanksgiving, and I’ll probably have a shit New Year’s, too,” you sighed, turning into the nearest men’s clothing store. Dean realized what you were up to.
“You’re not thinking of buying me another shirt, are you? Honestly, I’m fine. The coffee’s almost dry now anyway and I can just wear that one once you buy yourself a new shirt,” he stated, pointing to his flannel that you were still wearing.
“I feel bad! That shirt is ruined, look at the coffee stain!” You exclaimed with a laugh, pointing at his gray tee.
“This thing? Nah, I got about 15 of them back home. C’mon, let’s find you a shirt so I can get my flannel back and get the hell outta here before there’s another accident,” he teased, and you rolled your eyes in protest and made your way back out of the store. “So, why the shit holiday season?” He questioned, continuing the conversation as the two of you started walking again.
“Ugh, where do I start? On Thanksgiving my little brother proposed to his girlfriend of six months –”
“Who proposes on Thanksgiving? That’s like, the least romantic holiday,” Dean interjected.
“I know! That’s what I said! It just sucks because now I’m the only single person in my family, and being a girl, and being the oldest, it’s like… everyone expects me to be married and have kids by now. So, I’m getting bombarded with questions about whether or not I have a boyfriend at every holiday and it makes me want to rip my hair out. And then on Christmas, as if Thanksgiving wasn’t bad enough, my mother invited her new next-door neighbor over for Christmas dinner so she could try and set me up with him!” You exclaimed.
“Oh, no, that’s rough,” Dean chuckled. “Did you like him?”
“Even if I had, I would never go on a date with someone that my own mother set me up with. I mean, she’s lost it, she wants grandbabies so damn bad. What about you? What made your Christmas so rough?”
“Oh, God. I decided to go over to this girl’s parent’s house for Christmas dinner… it was our second date,” he said nervously, as if you were about to judge him for his actions.
You laughed. “Why would you ever say yes to that?”
“I didn’t want to be alone on Christmas! But after being shown the third baby photo album of hers and then being forced into wearing a matching sweater, I was regretting the decision, trust me.”
“Oh, God. They sound –”
“Crazy? Yeah, it was fuckin’ freaky,” Dean said with a shiver as he recalled the memory. “So, what are your plans for New Year’s then?”
“I got invited to this party at this club but Lord knows I’m not going to find a date by then. So, it’s like, do I want to spend New Year’s alone at home or do I want to spend it alone at a club? That’s why I came here in the first place; to find a dress,” you explained.
Dean nodded as he listened. “Well, I don’t have any plans for New Years,” he hinted. You cringed. It’s not that you weren’t attracted to him, it’s that you genuinely just… weren’t a relationship person. And as much as you would love to have a New Year’s kiss, you wanted to have a New Year’s kiss with no strings attached, and something told you that Dean wanted the strings. You finally reached your favorite clothing store and stopped to face Dean before entering.
“Look, I appreciate the offer but I just really can’t start a whole relationship thing right now and –”
“Woah, woah. I never said anything about a relationship. I’m not a relationship guy myself. I just… I was thinking, because I need a date to this work thing I have going on on Valentine’s Day, if I go to this New Year’s party with you… would you maybe consider returning the favor for me?” He asked hopefully.
“Like a holiday date?” You questioned as you narrowed your eyes at him skeptically.
“Yeah, yeah exactly! Like… like a holidate,” he smiled, clearly quite proud of his pun.
“I was considering it until the pun,” you joked. You had to admit, it was a pretty good idea. It took the stress of finding a date for the holidays, and he wasn’t the worst person to be around. “Fine, fine, I’m in,” you agreed, before making your way into the store.
New Year's Eve
You and Dean had exchanged numbers later that day at the mall, after you had given him his flannel back and thanked him for helping you keep some of your dignity. You hadn’t heard from him until yesterday, when he texted you asking if you wanted him to pick you up. You took him up on the offer, figuring that it would do you some good to save a little gas money. Plus, this was technically a date. A non-romantic date, but a date nonetheless. You took one last look at yourself in the mirror, straightening out your sparkly black skin tight dress that you had actually picked out at the mall that day, after you said your goodbyes to Dean. The dress stopped about mid-thigh and showed off your cleavage quite nicely. You felt good in it. Hot. Sexy, even. You were ready for a night out to ring in the New Year with friends who wouldn’t be bothering you with silly questions about your love life, because for all intents and purposes, tonight, you actually had one. There was a knock at your door and you yelled, “Coming!”, as you rushed out of your room, trying to simultaneously put your heels on as you did so. You unlocked the door and opened it, one shoe on while the other was still dangling in your hand.
“Woah, you look… hot,” Dean stated simply, eyeing you up and down while you steadied yourself on the nearby wall and put your other heel on.
“Thank you, you don’t look so bad yourself. You can, uh, you can come in. I gotta grab my purse and make sure all the lights are off,” you smiled, as Dean stepped through the doorway and closed the door behind him.
“Nice place,” you heard him announce as you ran off back to your room to grab your purse.
“Thanks, it’s not much but it’s home,” you replied loudly, spinning in slow circles trying to figure out where you had left your purse. You finally spotted it on a chair under the clothes you were wearing before you had changed into your current outfit. You headed out of your room, turning the light off on the way out. “Alright, I’m good. Let’s go get drunk,” you smiled, as the two of you headed out the door.
The club was loud and crowded; just about what’d you’d expect, it being New Year’s and all. You found your friends and their dates rather quickly, despite the noise, the bad lighting, and the number of people. You introduced Dean as your date for the night, and judging by the looks on their faces, you knew you’d be getting questions about him later. However, it wouldn’t be the annoying question of, “Do you have a man, yet?”, it’d be the slightly less annoying question of, “So, Dean, huh?”, which you were more than fine with. Honestly, you quite liked talking about Dean. He was a mystery to you, and you liked it that way. Much less of a chance of you falling for him.
“Do you want a drink!?” Dean leaned over to yell in your ear over the blaring music.
You nodded. “Yeah, anything with whiskey in it, I’ll drink!” You replied back to him, just as loud. He smiled and gave you a nod before disappearing to the bar.
The night was moving quickly, and after your fourth drink, you were really having a good time. Dean had gotten a few drinks in him as well, and around 11:00 he had asked you to dance. The music was God awful. Just some new age, pop techno crap. It sounded like noise more than it did music, but neither of you cared. You had your arms around Dean’s neck, and he had one hand on your hip, the other holding a beer, while the both of you swayed to the noise-music. Dean took a swig of his drink and then leaned over to yell something in your ear again.
“I feel like I can say this, because I’m not actually trying to impress you, but I just thought you should know that your boobs look fucking amazing tonight!” He shouted, and you giggled.
“Thank you!” You replied, quite enjoying the open line of communication between the two of you, considering that you didn’t have to be cordial with one another because this wasn’t meant to be an actual, real, romantic date. “Did you see Caroline’s though? She looks so good in that dress, doesn’t she!?” You asked, nodding over to your friend who you had introduced to Dean earlier, who was drunkenly dancing with her date. Dean nodded in agreement as he glanced in her direction.
“Yeah, she does. You didn’t tell me you had so many hot friends!” he said in a joking manner, although you wouldn’t have minded if he wasn’t joking. You laughed.
“Yeah, we’re a good-looking bunch!”
“You’re the hottest one, though!”
You blushed. “You think so!?”
“Fuck, yeah! I mean, c’mon!” Dean replied, taking a step back to motion to your body with his hands. “Also,” he added, leaning back in close to your ear, “are we supposed to kiss at midnight!?”
You thought about it for a moment. “Yeah, I think so! It’d be weird not to, my friends would ask about it!”
Dean nodded as he took another sip of beer and smiled. “This is the best date ever! I mean, I can say whatever I want without having to worry about a damn thing!” You laughed in agreement as the two of you continued to dance.
It wasn’t long before the music stopped so the DJ could announce that it was 20 seconds until midnight, and before you knew it the countdown from 10 had begun as the numbers displayed on the giant screen at the front of the club.
“FIVE, FOUR, THREE, TWO, ONE! HAPPY NEW YEAR!” The crowd roared, as the music turned on again and horns and party poppers went off in all directions. You looked at Dean who grabbed you by your waist and spun you around into a dip, kissing you passionately as all the other couples around you did the same. You giggled into the kiss, not expecting the dramatic take on it, but you didn’t mind. And damn, was he a good fucking kisser. You pushed the butterflies in your stomach down as the kiss ended and Dean placed you back on both feet, reminding yourself that you wouldn’t see him again until Valentine’s Day, per your “holidate” agreement. However, the rest of the night was a little less fun with the kiss constantly playing at the back of your mind and the fireworks that you had suppressed threatening to erupt. You found yourself reminding yourself the same thing the rest of the night: You cannot catch feelings, you cannot catch feelings, you cannot catch feelings…