Hard to believe it's been about a year since I first started writing this story! What was once supposed to be a one-shot is nearly 70k words and counting. Thanks to everyone who has stuck around :)

"You are a saint for meeting me this afternoon," Caroline gushed as she flipped through hangers on a rack.

"Joys of working nights" Elena yawned. She could still be in bed right now if she hadn't answered her phone while half asleep, thinking it might be Damon. Instead, it was Caroline begging for emotional support. She was shopping for a last minute revenge Halloween costume in Whitmore, where there was better selection. Caroline would not take no for an answer. "Glad it worked out."

"I can't believe Tyler had the nerve to wait until three days before Halloween to tell e he could't handle the pressure of a couple's Halloween costume this year."

Elena could, having had several versions of this conversation over a period of 10 years.

"Which do you think says 'you'll regret letting me go for the rest of your life' more—sexy devil or sexy nurse?" Caroline held up two costumes, taking turns holding them up against her body in front of the mirror. The rustling of plastic from the bagged costumes hid the buzz of Elena's cell phone.

"What about sexy veterinarian? Subtly implies that you could neuter him." Elena suggested, moving further down the aisle to check her messages. The corner of her mouth turned up, as she turned away to type her reply.

Caroline hung the costumes back on the rack and followed Elena further into the store. "Sexy cat?" she volleyed, eying Elena's back. "Subtly implies I can scratch out your eyes and suffocate you in your sleep."

"A reminder that you are now free to roam like one, too." Elena returned her phone to her pocket and picked up a plastic axe, giving it a few experimental swings. "Sexy Lizzie Borden?"

Caroline ran her hand down a fake samurai sword. "Uma Thurman's character from Kill Bill is plain sexy…" she trailed off, deep in contemplation. "But no. I want something with a skirt."

Caroline began to fondle a knife dripping with fake blood. Elena grabbed her shoulders and steered her away from the weapons section, back towards the costumes. They both began halfheartedly flipping through racks of colorful polyester—Elena weighed down by exhaustion, Caroline with regret.

"Serves me right for giving him one last chance," Caroline grumbled, swatting away hangers.

Elena hummed her agreement. After their heart-to-heart in the bathroom at the Grill, it surprised her (kind of) to learn that Caroline and Tyler had gotten back together. She had a sneaking suspicion that the town rumor mill had something to do with it. Talk of Stefan and Caroline together must have stoked a few fires of jealousy on Tyler's part.

"But no more. If he can't even commit to a couple's Halloween costume, then what am I doing waiting around for him to commit to me?"

Another buzz came from Elena's purse. When Elena thought Caroline wasn't looking, she pulled out her phone. Caroline peeked over Elena's shoulder and saw Damon's name flash in the notifications.

"Are you still talking with Damon?" Caroline's eyes lit up, like they always did when she could sense gossip to be had. It was Caroline's version of a sixth sense.

"It's nothing," Elena insisted, pocketing her phone. "Try this one on. I think Sexy Pirate is a real winner." She turned and pressed the hanger into Caroline's hand.

Caroline smirked. "It didn't look like nothing when you left the bar together." She hung the costume back on the rack and crossed her arms. "Plus, you have that post-coital glow thing you always had going when you got back from your "study sessions."

Indeed, Damon and Elena had been sexting ever since she woke up. Elena knew she had been caught. "Fine. It's casual. He's fun to talk to," she conceded, her cheeks tinged pink.

Caroline returned to flipping through costumes with a satisfied look on her face. "Invite him to the Thanksgiving formal."

Elena gestured to their surroundings. "Don't you think Mystic Falls holds too many balls?"

Caroline raised an eyebrow. "We hold exactly the right amount. Don't change the subject. You'll be there, of course?"

"Um," Elena froze, realizing she had yet to request the day off. "Yes, definitely." She opened her phone again to make a quick reminder in her calendar. Her eyes flicked over the November first deadline for Whitmore's Early Decision applications, and her stomach clenched. She should be at home working on her essays. Not sifting through cheap costumes and rehashing the end—or pause, tbd—of Caroline's relationship.

"See if he can come. It'll be fun! I'm dying to know more about the lost Salvatore, and I'm sure he'd make a great date." Caroline wandered off towards another aisle then turned back to look at Elena with a saucy look on her face. "He'd look fabulous in a tux."

Elena rolled her eyes before following behind her friend. "You were never this insistent about getting to know any of my 'study partners'."

"That was college. This is different." Caroline waved her hand in dismissal and went back to perusing a rack of medieval looking dresses. "You're twenty-six."

"You make it sound like I'm a spinster," Elena scoffed. "And as if that's not something to aspire to."

"It's, well…" Caroline stopped her search and turned to face Elena. "You haven't had a relationship since Matt…" Since your parents died, is what went unsaid in the ellipses. More dots connected for Caroline. Elena opened her mouth, ready to protest. "Don't try to tell me it's just because you are busy." Caroline glanced at the bags under Elena's eyes. "I know you are," she said, lowering her voice. "Things have been different since you came back from New York. You've made more time for me. When we're together, you smile more. You're less distracted."

Elena looked away. She felt guilty for thinking about her essays. They were basically done. Had been done for weeks. From what she understood, her application to the research program was a formality, if anything.

Caroline waited for Elena to drag her eyes back to meet her own. "All this tells me is that it's a choice. And you've made good ones since you've met him. So sue me if I'm a little invested in seeing what happens if he sticks around." Caroline underlined her encouragement with a pointed look and a reassuring squeeze before turning back to the costumes. She plucked a few dresses from the rack and made her way towards the changing rooms.

Elena prickled. Typically, she disliked Caroline's tendency to meddle, which is why she never invited her "study buddies" back to their shared dorm room. That said, she conceded Caroline had a point. The past few months, she felt as if coming out of a cloud. Her trip to New York helped her discover the autopilot she had not even been aware she was on.

She trailed after Caroline towards the back of the store. She could invite him. It's not like it changed anything about the long term reality of her residency being in Whitmore and him running a bar in New York. She stopped outside of Caroline's changing room. "I'll think about it. He's probably super busy that weekend."

"He'll be there. That man looks at you like you invented blueberry pancakes." Caroline poked her head through the curtain. "Help me with this?" She beckoned Elena inside.

Caroline wore a deep burgundy velvet gown, closed by a corset. Elena wrestled with the ties. Another buzz came from Elena's phone right as she finished lacing up the dress. Caroline's eyes flashed with intrigue. "What's he been saying?" She asked, catching the blush of Elena's cheeks in the mirror. "Oh, is it spicy? Let me see!"

Elena peeked at the message and burst into a delighted chuckle. She turned the phone around to Caroline.

"I would like to file a formal request for you to show me your tits, spelled with two esses." Caroline read aloud.

"Are you drunk?" Elena texted back. They had been veering towards a super sexy chat, and this was…not the direction she thought he'd take things.

"Accidentally yessss," came the reply, seconds later. "Whiskey tasting, new sales rep."

"What are you waiting for? Do you want me to take the picture for you?" Caroline prodded.

"No, thanks," Elena laughed. She brought Caroline in for a selfie and sent it to Damon.

"Chicken," Caroline tutted.

His reply was instantaneous. "Decidedly not boobs. Say hi to blondie for me."

"Boobs later ;) I'll try to call you before my shift." Elena pocketed her phone with a smirk, and found Caroline inspecting her own reflection, eying the lace trim across her cleavage.

"You know I was planning to get a sexy dress, pair it with some cat ears and call it a day, but I like the vibe this is giving. Very Lady Macbeth." Caroline mused, as she surveyed her reflection over her shoulder.

"It sends a message." Elena agreed. "The meaning is up for debate, but you look great." She stifled a yawn. "I'm gonna need some coffee soon."

"We can go. I'd like to check a few more stores before making a decision. Let me get this off and I'll meet you up front."

*Cannot for the life of me remember how to do a page break on FFN*

"But if I were really interested in taking a gamble, I would buy that. It's where the real returns are."

Damon grunted in a way meant to convey complete and total ambivalence.

It all started earlier that afternoon, before the chaos of operating a college bar on Halloween ensued. Kyle was rolling silverware while Damon updated the point-of-sale software with the evening's drink specials. In an effort to make conversation, he asked Kyle, "What would you do if you won the lottery? Hypothetically speaking." He wasn't telling anyone about his windfall, but he thought about what he might do with it often.

Kyle lit up like he had been waiting for someone to ask him this exact question his entire life. "coin," he whispered, eyes widening like a man possessed, "with 20% stablecoin reserve, 15% speculative on memecoins, and 10% in ETH." Having already heard too much, Damon promptly excused himself to his office. Now, however, it seemed he had opened a door that refused to close. Anytime he was within earshot, Kyle took the liberty of sharing his cryptocurrency investment strategy in excruciating detail.

For most of the evening, it was easy enough to avoid. But it was the early hours of November first, and both sides of Bob's were slammed. Even fully staffed, Damon found himself needed behind the bar to pick up slack, where he was now subjected to Kyle's unfortunate ability to hold a one-sided conversation through a busy rush. The temptation to fire him was strong, but Kyle was slinging cocktails faster than he was rattling off crypto facts. It was as infuriating as it was impressive.

He felt his pocket vibrate. One hand kept shaking a tumbler as he dug out his phone. Text from Elena. It was 3:41am.

Just got home. I extracted one cassette tape from one rectum and only had to pump 15 stomachs, two less than the other resident on my floor tonight, so that's something. How's your Halloween going?

Mood much improved by her unexpected message, he pocketed his phone. "Hey Kyle, fascinating stuff. I just remembered something I have to do in the back. Hold down the fort."

"You got it, boss," Kyle saluted. "When you get back, I want to tell you about Solana."

Damon poured out four shots, set them in front of a pair of neon colored fairies. After wiping his hands on a towel, he grabbed their proffered credit card and set up a tab. As he made his way by, he slapped Kyle on the shoulder. "Sure thing, bud."

Damon wove his way through the gyrating mess of bodies covered in face paint and fake blood and glitter. He noted people went all out for the costume contest this year. His social media person deserved a bonus. Slipping into the back hallway, he was soon in his office. Once there, he plopped in his chair and placed a phone call.

When Elena picked up, whatever she had to say in lieu of hello got lost as she spoke around her toothbrush.

"Come again?" He heard the faucet run before she spat in the sink.

"Shouldn't you be working?" Elena repeated, before gargling her mouthwash.

"Promise me you won't tell my boss. I don't want to get in trouble." Damon was pretty sure he heard her say "Dick," before finishing with her rinse. The lack of enunciation gave the insult absolutely zero bite.

"I wanted to thank you for those photos, since we didn't get the chance to connect the other day." Elena had been on nights for several days in a row. That was the hardest to get in touch, because he was often at work by the time she was awake and sleeping when she got off of work. Sexy pictures took the edge off, though. "How much have you missed me? You can be honest."

"Oh, terribly," she laughed. She grabbed her brush and began working through the mess of tangles in her hair. "It's amazing I can even get out of bed." Her tone was dry, but there was some truth to her answer. Her interactions with Damon were easily growing to be her favorite part of each day.

A chuckle rumbled out of him, pleased with her answer. For a few moments he let the silence born of too many questions and never enough time to ask them all hang between them. He settled on "So…cassette in the rectum?

"Yeah… it was my last patient before the end of my shift, and by the time we were done, Halloween was in full swing, so I stayed on. Can we talk about literally anything else?"

"I don't know how you do it." Damon kicked his feet up on his desk.

"Coffee, adrenaline, savior complex." Elena mused. "Mostly coffee. God I'm exhausted, but still so wired. Maybe I'll go submit my application..."

"New grant?"

"No, it's for me to do a dual track residency and research PhD. Early decision deadline is tomorrow. Err…Today"

All Damon heard was someone incredibly busy about to become even busier. He let out a low whistle. "Damn girl. Do you think you'll get in?"

"Yeah, it should be a sure thing. My advisor made it seem that way, anyway."

"Great!" Damon hoped he sounded enthusiastic. It was exciting for her, but he could already feel the time he could get from her slipping away. It was already so little to begin with.

Elena waited for him to say more. When he didn't, she felt compelled to fill the gap in conversation with an explanation. "Yeah, I'm hoping that with the university's support, I can spend my time doing actual research, instead of filling out applications."

Damon buoyed a little at the news that some of it would be a replacement. Not an entirely new category to fill the minutes of her day. "Fingers crossed," he wished her, this time with a smile behind the words that felt more genuine. "Doctor Doctor Cinderella has a nice ring to it."

"Thanks!" Elena chirped, cheeks tinged pink, pleased with his understanding. "I mean I'm not in yet, but I'm excited about the opportunity to move things forward." She liked telling someone who got it. Caroline huffed and asked her if her research involved time travel, because that would be the only way she could get everything done. Her residency supervisor expressed something similar.

Butterflies made their way around her stomach as she gathered courage to bring up a topic that had been on her mind the past few days. She took out her moisturizer and nearly knocked her phone off of its precarious position balanced on the edge of the sink. Her contented reflection in the mirror shifted as she bit her lip.

"Actually, I'm glad you called," Elena began, rubbing lotion into her face. She took a moment to finger the skin under her eyes, wondering if there was a cream in the world that could make her look like she slept. Probably not. "How busy do things at the bar get around Thanksgiving?"

"Last year was hit or miss, but this is only our second go around, so hard for me to say." Damon replied, sensing hope bubble up through his chest. He pulled his feet to the ground and leaned forward in his chair, buzzing in anticipation of what the question might imply. "Why do you ask?"

"You've only been open for a year and change? The grime on the dance floor seemed like it had been decades in the making."

"Har, har," Damon deadpanned. "It was an acquisition, if you must know. Why do you ask about Thanksgiving?" He repeated her question, softer.

"Sounds like you will be busy, and there's a chance I won't actually get the days off—"

"Elena," Damon cut her off. "Just ask me," he implored, hoping his voice would not betray the simmering sense of desperation to hear what she seemed to be working towards.

"Ok." Having finished her bedtime routine, Elena sat on the edge of her bed, unclear why she felt so nervous. "There's a ball in Mystic falls—"

"Another one?" Damon was incredulous. How many formal events could one small town sustain?

"Yes, another one," Elena laughed, "For Thanksgiving, a charity ball. Caroline was in charge of picking the recipient for the proceeds, so this one benefits Whitmore's PhD research program. I'll be there to talk to people and give a small speech." She closed her eyes and inhaled a sharp breath before asking, "Would you like to be my date?"

Damon collapsed back in his chair with a shit-eating grin on his face."Would I have to wear a tux?"

"True, I forget not everyone has those lying around." Elena pressed a palm to her forehead. "Forget I said anything."

"I have a tux," Damon all but purred, lips still turned up in a smile. He stood and started to meander around the room. "I ask because it needs to be pressed. Would be a shame if your date showed up a wrinkled mess."

Elena fell back on the mattress, releasing a breath she was unaware she was holding. "Really? Ok, great, I'll send you the details." Her unexpected nerves were immediately replaced with delight at his acceptance. Now that he had said yes, she wondered what took her so long to ask. Logically, she knew he would want to come. He had been more than clear about his desire to get together again over the past few weeks. It must have been a latent fear of rejection, given that she had not asked anyone out to do anything in… well, forever.

"Looking forward to it," Damon affirmed, excited to see her in a scenario where he could look extra dashing. Though, something was bothering him. He thought about the picture she sent the other day. The one from when she was out with her friend with the bossy disposition he met at the bar. Suddenly he had to know. "Did Blondie put you up to this?"

"You think I would need outside pressure to want to hang out with you?"

Well yeah, took you long enough to ask yourself, he thought, only slightly bitter. "You have dodged every inquiry I made about when we could get together over the past few weeks." The truth of the statement hit him as soon as it left his mouth. The realization settled uncomfortably in his gut.

Elena's brow furled."I... am out of practice, I think. My schedule doesn't allow for much advance planning." She also wondered if this was the whole truth. "I can't wait to see you," she breathed. That much was.

"Same." Damon mulled over her response and found his stomach quiet at her admission. He sat down on the edge of his desk, overwhelmed by the desire to hold her again. All previous doubts erased with the realization he would be able to in a few weeks.

Damon thought about saying, "I'd give anything to have you in my arms right now." Instead, he listened to the soft rustling of covers as Elena climbed into bed. He imagined what it would be like to be there next to her.

Elena made herself comfortable sitting up against her headboard. She thought about apologizing for taking so long, sad to have caused him seeming discomfort. But there was no lie in her explanation. She opted for, "I'm still not ready to sleep."

Damon sat at the edge of his desk. "You would be if I were there," he said, voice drenched in sultry promise. "I give good cuddle."

Elena slid down under the covers. "Would we be sleeping?" It was a valid question.

"Eventually we'd have to."

"Mmm…sounds nice." For a few moments, Elena lost herself in the possibility of what could happen in a few weeks time. When Damon didn't say anything, she assumed he was doing the same.

"What was your Halloween costume?" she asked through a yawn.

"What? Oh…" Damon cleared his throat, his voice all of a sudden quite rusty. "Vampire." Though he had long taken out the teeth and wiped away the dribble of fake blood. Now he was just a tired bar manager, albeit an exceedingly handsome one. He listened to the slow rise and fall of her breath for a minute before saying, "Go to bed, Elena."

There was a muffled sound as the phone fell from under her neck onto the pillow beside her. He pulled his phone away from his ear, then put it back to listen for a moment longer before he ended the call, a half-smile playing on his lips. Standing up, he adjusted his pants and directed himself out the door.

He made his way back to the main bar, still packed, despite their official closing time in less than an hour. Kyle seemed to have everything under control, so he walked the perimeter, surveying the crowd. Towards the back, he found Bro #3, sitting in his usual booth, but sporting a scarecrow costume in place of his usual hockey jersey. They exchanged head nods. Damon slid into the otherwise empty booth. For some time, they sat in companionable silence, while the rest of the bar pulsed in Halloween revelry. After some time, Damon asked, "What would you do if you won the lottery?"

Chett (he was pretty sure that was his name) thought for a moment before he replied. "'I will make this my winter home, have another house for the monsoon, and dwell in a third during the summer'—lost in such fancies one forgets his final destination."

"Real Housewives?"

Chett shook his head. "The Dhamapadda." He turned to watch the closest screen, where Nosferatu played on repeat, eyes puffy and red.

Damon hummed in surprise, wondering when Bro #3 became such a Buddhist.

"Are you OK?" Damon asked.

"Yes and no," Chett sipped his beer. "I broke my world of delusions, which caused me grief. But I also don't want them back. So yes and no."

Damon nodded in approval. Not what he expected to hear.

"You're busy," Chett said. Damon met Chett's glance as Chett sipped his beer, knocked twice on the table, and set off to see where else he could be useful.

So there we are! You may remember that this section of phone calls was added last minute in order to properly flesh out their long distance relationship. Originally, I intended this all to be one full chapter, but it's amazing how a short synopsis can turn into 15k words! Next chapter will be the last of these, and then we're back into the arc I planned a year ago. Wild. This one would probably hit better when paired with what I have planned for the next, but given I am the world's slowest writer, I figured an update was better than no update!

Not much else to say, then, except I hope you have a phenomenal Halloween. Certainly better than Elena's :P

See y'all here next month-ish! Be well ️