Chapter Text
Seven Days Until Christmas
Alex could kill Jessica right now.
Hyperbole, perhaps, but here he was in a mall, the week before Christmas tasked with buying a week's worth of ugly holiday sweaters. Sweaters that he'd have to wear and post the evidence every day on Instagram until Christmas. He should have known better than to make a bet with her.
As he walked through the thick crowds of barely moving people, wandering through the mall almost completely unaware, he mostly cursed himself for daring to make such a stupid bet that required him to set foot in a mall during the holidays. He didn't like shopping at the best of times, but visiting a mall just before Christmas was downright right masochistic.
What is too much to ask people to fucking pay attention to where they were walking?
To have some courtesy and keep to the right if walking so slow, it seemed as though they were barely moving?
To not stop randomly in front of him, jaws slack, oblivious as they looked around trying to find where they were going?
To have some iota of control over their children, so they didn't collide with him as they ran, weaving their tiny, hyperactive little bodies through the crowd?
Yep. It was too much to ask.
The worst part was, he didn't even know the first place to look.
He started in the department stores and struggled to find anything that was actually ugly.
Lots of sweaters.
But nothing that Jess would think was ugly enough. And department stores were so big it took a significant amount of time to move through the store and find, or rather not find, what he was looking for. Alex thought about asking a staff member for help. Still, they all seemed so frazzled and overworked that he actually felt bad enough for them that he couldn't foist his own misery on them.
Next, Alex visited every shop that he figured would sell stupid, ugly, Christmas sweaters. Novelty shops that sold movie posters, t-shirts with crude slogans and plastic dick water bottles. There were ugly sweaters in that store, but Alex refused to purchase the red and green sweater that was covered in festive holiday penises. Jess would enjoy that, but Alex could feel his brow furrow and face contort in a frown as a single thought danced through his head: Who actually purchased this crap?
Alex was getting tired when he reached a shop that was tucked away in a lower traffic area of the mall.
It was one of those shops that mostly sold really cheap, mass-produced clothes—racks of $5 t-shirts and two for $20 pants. There was only one store clerk, and the store was dead—finally, some solace from the busy, crowded shops in the high traffic areas of the mall.
Alex slowly moved through the cramped racks of polyester blend clothes that had a faintly chemically warehouse smell when he came upon the proverbial jackpot.
The sign read: Holiday Sweaters 2 for $20
It was still going to cost him almost seventy dollars before sales taxes to fulfil the terms of this stupid bet. Yet, on the plus side, his search was over and he'd be able to leave this wretched place soon.
He started sifting through the almost itchy feeling cheap acrylic sweaters. Alex wasn't sure why he was spending so time selecting sweaters like it really mattered if he found the fucking perfect sweater. He pondered the choice between a baby blue Frosty the Snowman sweater and a shit brown Rudolf the fucking reindeer number, finally settling on why not both and slung both sweaters over his arm.
As he sifted through the rack, clutching his two sweaters, he heard a voice behind him.
"Do you want me to start a fitting room for those?"
Alex turned to see a slim guy with a mop of dark brown curly hair, hazel eyes that twinkled mischievously, lips curled into a half-smirk that almost seemed like it was mocking him. He was dressed far too fashionably to be working in such a cheap clothing store, from his expensive shoes to a scarf that was perfectly arranged around his neck.
"Uh, no I think I'm good." Alex briefly made eye contact, steeled his jaw and went back to his mission to find more ugly holiday sweaters.
"Ok, well, if you change your mind..." the other boy's slightly husky voice trailed off.
"I won't," Alex said curtly, not looking up as started to move the garments along the rack more aggressively.
Alex selected another sweater, this one a bright red with what appeared to be a Christmas tree that had tiny lights that would light up if he added a battery, sold separately of course.
The voice piped again, chuckling, "Nice pick. Really classy. I have to know why you seem to be on the hunt for not one, but three ugly Christmas sweaters?"
Alex sighed, "Don't you have something better to do than watch me pick out sweaters?"
"Clever, answering a question with a question. Can I bring these to the till for you?"
"Sure," Alex replied, hoping this store clerk might leave him alone with his miserable task. However, he was back in a few moments.
"Look, I'm fucking bored, and no, I don't have anything better to do because it is literally my job to help you. You'd think this place would be hopping due to our fine selection of holiday attire, but apparently, the rush for such things occurs in late November before Christmas Party Season. Nobody wants ugly sweaters just before Christmas."
"Well, I guess I'm fucking nobody, " Alex grimaced, selected a green cardigan with red trim and an assortment of holiday images like Santa and mistletoe.
"Shall I stick this with your others?"
"Thanks," Alex nodded and passed the other boy the sweater so he could bring it to the pile that he had started
The clerk returned and started going through another rack, pulling out and holding up a red sweater that had a white image of The Dude and his infamous quote The Dude Abides.
"How about this one?"
"No way! They seriously make sweaters with The Dude on it? The Big Lebowski is one of my favourite movies."
"Yep, they didn't ship us many. I think this is one of the last ones. I am a fan myself."
The clerk licked his lips and grinned, and Alex swore that he might be flirting with him.
"OK, maybe I shouldn't have been so quick to pass up your help. Any other gems?"
"Only if you tell me why you seem to be buying a whole holiday wardrobe of hideous sweaters."
Alex rolled his eyes and let out a breath.
"My best friend and I made a bet, and I lost. Now, I have to wear an ugly sweater for the seven days leading up to Christmas and post pictorial evidence on Instagram every day."
He laughed, "Well, my name is Winston, and I'd be happy to help you select the last couple of sweaters."
Winston was bored until the customer who wanted to buy a week's worth of ugly Christmas sweaters entered his store thirty minutes before close. Average height, light brown hair and pretty cute for a guy wearing the type of scowl mothers warn become permanent if you sport them too long. Most customers didn't want help, but it was his obligation to ask, and if Winston was honest, it was an excellent excuse to get a closer look. As with most customers, he was resistant, but Winston was happy; he finally let him assist.
"So are we going for the ugliest sweaters?"
"I'm not even sure anymore. I mean... shouldn't it be fucking easy to just pick seven sweaters?"
"Easy if you don't care, but you seem to care."
"I just... I don't want something that says Jingle Balls on it . " His picky customer held up a sweater with exactly that saying.
"Ah, ok so PG13?"
"Yeah, and you seem to have a lot of sweaters with this sort of light punny innuendo."
"Like I said before, we sold like half our stock the last week of November. How about this one?" It was a black sweater with the word BOOM! in green with a pickle on it.
Alex laughed, "That's PickleRick from Rick and Morty! Yeah, put that one in the pile."
"Ok, so we need one more sweater."
They continued to sift through the sweaters, Winston periodically holding an item up and the other boy shaking his head.
"Look, I have to close in five minutes, how about this one?" Winston held up a red sweater with a frowning gingerbread man with a bite taken out of its face.
"It's perfect."
Winston was struggling to believe that this person didn't care at all given he'd spent 25 minutes picking out sweaters. But there was something really endearing about him, Winston couldn't help but be intrigued and simply had to see this guy again. He walked purposefully behind the cash register.
"Ok, so that will be $75.10."
"I'll pay debit. Shit, that is a lot of money."
Winston hadn't always had to worry about money, but certainly understood now. He was working that shitty retail job because he no longer wanted the money that came with strings attached from his father. Luckily, his grandparents were paying for his education and his rent. The job was to cover the rest. An idea suddenly came to him as to how he might see this mysterious sweater shopper once more.
"Listen, I get being short on cash, and we have a final sale policy... but I might be able to swing something if you go for coffee with me."
"I um.... "
Winston sensed his nervousness; he was nervous too. It had been a while since he'd done this.
"Not at a date. Just as friends. Looks like you could use a friend that doesn't make bets with you that result in ridiculous wardrobe choices. Just leave the tags on."
"Uh... ok. Just a friendly coffee."
He hoped it might turn into more. He smiled. "Yeah, as friends or at least we could say, potential friends."
Alex smiled, eyes twinkling, "Well, if we are going to be potential friends, you should probably know my name."
Winston grinned, now he could swear this mysterious boy was flirting with him.
"And what would that be?"
"Alex."
Winston grabbed the printed receipt and scrawled his name and number on it before shoving it into the bag.
"Just text me, and I'll have your number, and we can arrange coffee. Now, go, so I can close up before I get any last-minute shoppers," he urged, winking.
"Thanks for your help." Alex smiled gratefully.
"Anytime."
Winston followed Alex to the entrance of the store, pulling the security gate across the entrance of the store watching Alex walk away as he did. What started as a boring shift really turned itself around in the last half hour. He was genuinely intrigued by the grumpy, attractive boy on a mission for not one but seven perfect ugly sweaters.
Especially someone who could power through wearing itchy acrylic for seven days in a row.
Winston shuddered at the thought as he finished closing up for the night.
Six Days Until Christmas
Jessica went over to Alex's apartment the day after his shopping spree to inspect his haul. Alex noted she looked smug, relishing in her win. They'd decided that as part of the bet she'd choose the first sweater and take the first picture for his Instagram post. Alex watched as she laid out each sweater on his bed almost gleefully, periodically laughing loudly at each pick. As she pulled the last sweater out of the bag, the receipt with Winston's phone number on it floated to the ground. Alex tried to grab it before Jessica, but she beat him to it.
"Shit, Alex. Is this what I think it is?"
Her eyes were alight with glee.
"Give that back to me!"
Jessica held the receipt out of reach as Alex tried to grab at it. She hopped up to stand on his bed to try to get it farther away from him.Alex followed her and grabbed her arm, but was unsuccessful in retrieving it.
"Okay, okay, okay... I will give this back to you if you confirm that the shop clerk at the store that you purchased this fine collection of sweaters, gave you his phone number."
Alex blushed.
"Jesus Christ, have you texted him yet? Is he good looking?"
"No I haven't and...." Alex's voice trailed off, and he got a kind of faraway look in his eye.
"Oh my god, he is cute, isn't he?"
"Shut up. Give it back to me."
"I don't know, you never actually confirmed it was the shop clerk."
"It was, and I wasn't going to text him."
"Why not? He's cute, you are single. I actually don't see why you wouldn't."
"I... just I don't know if I'm ready to start dating again."
"Alex, it's been almost a year since you and Charlie broke up. What's holding you back?"
She was right. He had broken up with Charlie just after New Year’s last year. It was after having done four horrible months of long distance through Charlie’s first semester at Harvard. Alex knew he couldn't do another three years in a relationship like that and noticed his feelings for Charlie had grown to be that of deep friendship rather than romantic love and he couldn’t stand the thought of stringing a guy as nice as Charlie along when he didn’t feel the same level of love. It wasn’t fair.
"I don't know, I guess I'm just scared? He invited me for coffee and did say we could just be friends."
Jessica chuckled and raised her eyebrows, "Did he?"
"Yeah, after I hesitated..."
"See? You've got nothing to lose."
"But I got the distinct impression that the friend thing was just to get me to go for coffee with him."
"So what if it was?"
Jessica shrugged, and while Alex was distracted, Jessica grabbed his phone, entered his lock screen password which happened to still be her birthday, and managed to enter Winston as a contact and text him.
Alex (3:26 pm): Hi its alex
After she finished, she handed back the phone and receipt and, for the second time today, looked smug.
"You bitch!"
Jessica put her hands on her hips and flashed a glare at Alex.
"What did you just call me?"
Alex's phone vibrated.
His brow furrowed into a frown. "You heard me. He already texted me back?"
Alex hesitated briefly before looking at the phone.
"What does it say?"
"Just hi alex. "
"Well, it is more of a start than you had before."
Alex rolled his eyes, "Thanks for that."
"You'll thank me one day."
"Will I?"
"Now, let's get your first photo taken and posted."
"Yes. Let's," Alex said dryly, as he pulled the first sweater over his head.
Jessica took the picture and posted it on Instagram. There was something poetic about how Alex's scowl matched the unhappy gingerbread man on his sweater.
Alex realised he was going to see a lot of Jessica's smug smile over the holidays.
Winston smiled when he saw Alex had finally texted him. He half expected to never hear from the mysterious ugly sweater boy. But when Alex didn't text him back, Winston started to worry he'd imagined the last message. He hadn't had a crush on someone like this in awhile. In high school, he'd been pretty quick to hook up with almost anyone who'd have him. Not to mention, his last relationship had been seriously unhealthy and really messed him up. He decided to stay single awhile and hadn't dated or even been with anyone casually for a whole year.
So while outwardly Winston was pretty sure he looked confident, inside he was a ball of nerves. He didn't want to text again without a reply or send a second text too soon and look desperate or clingy. He took a deep breath and tried to talk himself down from the anxious spiral he could sense his brain was headed down. His ex had been horrible about not answering text messages on purpose, withholding responses as a way to manipulate him. He continued to do some deep breathing in an attempt to calm himself down.
Inhale.
Winston closed his eyes and told himself, This isn't the same situation, calm down.
Exhale.
He knew that the best course of action would be to leave his phone somewhere and take a walk to distract himself but was struggling to put this sage advice into practice, and instead, he opened Instagram and tried to find the mysterious boy. With only a common first name to go on, it would likely be impossible, but it would distract him.
It took him about an hour before he found the account. He chuckled to himself because the photo was perfect. It was uncanny and Winston thought that he'd ever see the day that someone's facial expression would so perfectly match the image of a sad gingerbread man on an ugly holiday sweater.
He made a decision right then and there.
Fuck appearances.
He was going to send another text because it was better to have tried and failed than to not try at all.
Winston (7:36 pm): So about that coffee, when would you like to go?
The room was illuminated by the light of the film, alternating light and dark. One of Alex and Jessica's holiday traditions was watching It's a Wonderful Life together. They each sat on one end of Alex's couch holding their own bowl of popcorn. Alex found it a little weird because this would be the first Christmas in two years that Charlie didn't join them. He wasn't sad, but there was a sort of emptiness that came with the absence of a person. Their relationship hadn't ended badly, but they were still working on the whole friend thing and Charlie had been keeping his distance. Alex understood, but it didn’t make it any easier.
Alex's concentration on the movie was interrupted by the vibration of his cell phone. Jessica leaned forward to grab it and the look Alex shot her said, don't you dare.
"Who is it?" she asked excitedly.
"Thanks to you, Winston is asking when I'll be going to coffee with him, " Alex deadpanned.
"And? I don't see how this is a problem. It's just coffee."
"What if it isn't just coffee?"
"Then it isn't just coffee. Stop overanalysing things, Alex and start living."
Alex hated when Jessica was right. He shot her a glare as he picked up his phone, unlocked it, and opened Winston's message. Alex stared at it for a bit, hesitating before composing a reply. He was nervous. Easy for Jessica to tell him to stop overanalysing, much harder for him to actually do it.
Alex (7:45 pm): well i still have 6 more days before i can return the sweaters
Winston (7:48 pm): u do. we can have coffee before that. i'll still uphold my end of the deal later
Alex thinks about it a bit, best sooner rather than later as he'd likely work himself up too much if there were too many days between now and then.
Alex (7:50 pm): tomorrow?
Winston (7:51 pm) : cool, 7 pm at Rise and Grind ?
Alex laughed. Was that actually a real place?
"Uh, Jess, he wants me to go to Rise and Grind , have you heard of it?"
"Oh, yeah- it's that new shop near the University. I've heard it's good."
Alex shook his head in disbelief.
Alex (7:52 pm): cool, see u then
Alex leaned back into the couch, face looking slightly pained as he looked over at Jessica, who was smiling widely.
"What the fuck did I just do?"
"Took the first step in getting back into the dating game."
"He said it wasn't a date."
"Sure he did," Jessica smirked.
"Shut up!"
She made the motion of zipping her lips, but her eyes were still playfully mocking him.
Alex just shook his head and sighed. This would be a long seven days.