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Summary:

Dean Winchester has owned and operated Book Haven for the last six years since his mother fell ill. Before Dean, she was the proprietor, as her father before her. The book store has been a landmark in the old part of the city for three generations. They have many loyal customers who often come in for a good book, some local gossip (courtesy of Charlie), and a friendly face. Lately, Dean’s business has been threatened with the encroaching presence of a new, mammoth, Garrison Books branch opening barely a stone’s throw from his (admittedly fantastic) window displays. To top it off, the CFO of said behemoth, one Castiel Novak, is possibly the most infuriating, self-righteous asshole that Dean has ever had the misfortune to meet. At least he has his loyal staff, weekly calls from his hotshot lawyer little brother and a budding something with a stranger on the internet he knows only as angelofthursday…

Notes:

This AU has been inspired by one of my favourite romcoms, You've Got Mail. I have taken a few liberties, as fas as story and plot go, but the basic gist of the film is all still there. This has been a year-long project, and the longest piece I've ever written. Longer than everything I've ever written combined. I'm glad it's finally finished, and I'm excited to finally be able to show all of you :)

Enjoy ;)

Chapter 1: Dean

Chapter Text

Dean awoke to the high-pitched whine of a hairdryer coming from the adjoining bathroom.

He had been in the middle of a wonderfully peaceful dream, driving his beloved ’67 Chevy Impala down the unusually deserted streets of downtown New York, windows down, music cranked... When he noted the soft light growing behind his closed eyes and the draft on his leg, bared to the room during the night by the dishevelled duvet, he fought fruitlessly to postpone his return to chilly, noisy consciousness. He lay there for a moment, refusing to open his eyes on the off-chance he’d drift back into sleep. He waited. Tried to envision himself behind the wheel again, speeding down 5th avenue...

No dice. He turned over, away from the light that was slotting in through the half-closed drapes and tucking his leg back under the covers.

A quick glance at the clock on the bedside table told him it wasn’t yet 7:00. Of course he’d be woken up early the one day a week he takes a later shift at the store.

Actually, Dean could have sworn Bela had told him that she had the morning off as well. Why the hell was she up so early?

He heaved a sigh and pulled the covers higher, burying his face deeper into the pillow and trying in vain once more to recapture the dream. The racket stopped and a moment later, he heard the bedroom door open. He pretended to be asleep.

It wasn't that he didn't like Bela... She was gorgeous; tall, blonde, eyes the colour of pale jade, even had an incredibly sexy British accent to boot. He liked her, but lately he'd been wondering if they rushed into the relationship too fast. She was practically living at Dean's apartment and they'd only been dating for four months. She was great, but she could be a bit... challenging to live with at times.

"Dean." Bela thumped him hard on the shoulder. "I can tell when you're not sleeping. Come and see me off."        
Dean cracked one green eye open. She was standing beside the bed, dangerously high heels in hand, wearing a grey pencil skirt, a plum-coloured blouse and an impatient pout.

“Thought you didn’t have work ‘til later?” Dean mumbled against the pillow.

Bela waved her free hand dismissively and stalked over to the chaise at the foot of the bed to slip on her shoes. “That was before the gallery called me for an emergency meeting with a very prestigious potential buyer.”

Dean closed his eye again and groaned, rolling off the exceptionally comfortable memory-foam mattress he’d splurged on shortly after moving into this apartment a year ago.

Bela waited with a hand on her hip as Dean dragged himself out of bed and plodded the few steps over to his well-dressed, sophisticated art dealer girlfriend. She jutted her chin forward and he leaned down to give her a quick peck on the lips.

Down on the already bustling New York City street, a taxi honked its horn.

“That’s me. Gotta run.” Bela snagged her oversized bag from the hook on the back of the bedroom door.

“See you tonight?” he called as she headed for the foyer.

“Let’s get some take-out!” she replied as she rushed out the front door.

He let the peace and quiet envelop him like a soft blanket, and blinked the sleep out of his eyes as he wandered in the direction of the kitchen. He poured himself a cup of coffee from the pot Bela brewed earlier, and turned off the percolator. Mug in hand, beginning to feel more relaxed now that he had the place to himself, he headed to the living room where his laptop was sitting on the coffee table. He dropped to the couch and booted up the computer, excitement tingling under his skin at the thought of another message from Thursday.

A month ago, on his thirtieth birthday, he found himself in a random chat room online. He and his younger brother, Sam, were both thoroughly sloshed at that point, having left the bar early to come back and have a few drinks on their own before Sam’s return to Buffalo in the morning. Sam was in the middle of a pretty high-profile case and he’d had to all but bribe his fellow councillors to give him two days off from proceedings to come down for his big brother’s birthday.

He’d also had to leave his wife, Jess, and their fourteen month old son, Henry, on their own for a couple days. Jess had sent her love and wished Dean a happy birthday on the phone when Sam called to check in upon arrival. Dean was always thrilled to have some one-on-one time with his brother, but he kind of wished they had come down too. It had been months since he’d last seen them.

Sam had been a bit reluctant to leave his wife to deal with their young child alone, but Jess wasn’t feeling up to a long drive, and sent Sam out the door with a knowing smirk and a kiss, professing that she ‘wouldn’t want to get in the way of the drunken brotherly bonding anyway’.

Said brotherly bonding had consisted of a case and a half of beer, a fairly one-sided conversation about Dean needing more friends, and – Dean wasn’t entirely sure how this happened – a ridiculously juvenile game of truth or dare. It was shortly after Sam pointed out that only three people had attended Dean’s birthday celebration at the bar that evening, that Dean had picked ‘dare’, and Sam, cocky after his fifth bottle of Bud decided it would be hilarious if Dean took to the World Wide Web to try and ‘make some friends’. The guy couldn’t count past 10 without using his fingers right now, but he wasn’t too drunk to remember the URL for the chat service his creepy Stanford roommate had always been on.

That’s how Dean ended up on some sketchy website that had likely been featured on Dateline, at 11:45pm on a Saturday, talking to a seemingly normal guy he knew only as ‘angelofthursday’. Dean thought the username sounded a bit feminine at first, and was frankly, a bit surprised to discover that he was talking to a man after a few minutes of alcohol-induced flirting, which he promptly ceased; mostly out of consideration for the other guy and just to cover his own ass. You never know who swings in which direction or how pissed off they’ll be if you get it wrong.

Dean had discovered a long time ago that he was more or less equally attracted to women and men alike. It wasn’t until his senior year of high school that he discovered the official term, and not ‘til his twenty-third birthday that he worked up the courage to tell his brother. Surprisingly enough, Sam wasn’t completely shocked. He was, however, very supportive and happy that Dean had felt comfortable telling him. Dean was grateful for that, but he couldn’t figure out how Sam had known. His wise younger brother had cocked an eyebrow and delivered unto him three words: Doctor Sexy, MD.

Sam convinced him to tell their parents at dinner a week later. With Sam smiling up at him reassuringly, Dean had stood up from his seat at the table, announced that he had something to say, and with shaking hands and a wavering voice, had told his Mother and Father his well-kept secret. Or so he thought. Apparently, he was the only one still under that impression. His mother had risen from the table to gather him into a hug, and told him that they’d known for a while. His dad had just nodded from his seat, a small smile threatening to break the surface of his otherwise calm facade. When he asked them how they’d known, Mary had simply replied with another famous name: Captain Kirk. Sam had laughed for days about that one.

Once the most important people in his life knew and accepted him, Dean didn’t care who else knew. It was freeing.

Regardless, Dean wasn’t about to go and make some guy uncomfortable. He’d made the mistake once or twice of hitting on the wrong guys. Rarely did it end well. This guy hadn’t seemed all that receptive to Dean’s advances anyway.

For the next few hours, they discussed everything; music, movies, what they were doing in seedy chat rooms past eleven on a Saturday... The only things that they left barred were identifiers. Name, appearance, address, job; they decided it was for the best, since neither one was expecting this to go beyond one chance encounter.

By the time the conversation had slowed, and Dean’s alcohol-doused brain was demanding sleep, and Sammy had been passed out on the sofa for a good hour, they found that neither one of them wanted to say goodbye. Dean couldn’t explain it, but he’d felt a kind of connection with this stranger. He didn’t hate it, but he was a bit apprehensive about becoming pen pals with a person he knew nothing about.

Well, to be fair, not nothing.

He knew that his musical tastes were vastly different from Dean’s, and that he had a cat named Inias.

He knew that he tried to eat mostly organic and locally sourced food, but had an infallible weakness for White Castle burgers.

He knew that, like Dean, he lived in New York and that he liked to go for long walks through the city at night when it’s all lit up and dazzling.

So despite every rational bone in his body telling him that this was a bad idea, he exchanged e-mail addresses with the guy. He hit a snag when he realized that the only e-mail address he had contained his full name. He hastily set up a free e-mail account and used his chat handle – the first thing that had popped into his head after a night of drinking: Zeppelin67 – to complete the address.

By the next morning, waking up on the floor of his living room, Sam still sprawled out on the couch, dead to the world, Dean had forgotten all about the chat room. It wasn’t until later in the day, after he had seen Sam off, and thanked him for the hundredth time for coming down, that a quiet beep from his computer signalling an incoming e-mail had jogged his memory. He stared at the screen, the browser tab housing the free e-mail site still open from last night, now flashed ‘(1) New Mail’ at him impatiently. He clicked on the tab, and there it was. The first of many e-mails he would receive from angelofthursday.

Over the next four weeks, they corresponded daily. Dean would talk about how he hated taking the subway and leaving his Baby in the parking garage every day. Thursday would counter with some ridiculous thing his cat did and how, aside from the constantly, inexorably congested roads, the rising cost of gasoline should be reason enough for anyone to take public transit. They were conversations about nothing, but as a whole, it was quickly becoming something.

Dean sipped his coffee and flicked absently through the newspaper on the table as he waited for his laptop to start up. As soon as the desktop appeared, he opened the browser and hit the bookmark for the e-mail site with probably way too much enthusiasm, but he was the only one here and he didn’t care.

In just four weeks these e-mails had become more enticing than the increasingly banal conversations he struggled to maintain with Bela, and while he did feel a bit guilty about that, he relished the little burst of excitement that surfaced every time he saw a new message in his inbox. As strange as this whole situation was, Dean was becoming more and more attached to this anonymous, text-based relationship. So much so that every time he checked his inbox and found it empty, he couldn’t help but feel disappointed.

Today, he was not disappointed. He unconsciously held his breath as he clicked on the link to open the message and grinned as he read Thursday’s latest letter.

---

Date                                 From                                 Subject
Monday Feb 24, 2014     angelofthursd....              (no subject)
6:27am

                Monday mornings are inarguably the worst thing that could happen to a 5-day a week, 9 to 5 type of working person. Especially when said person was coerced into going bar hopping on Sunday night until 3:00AM. I guess it serves me right for believing my brother when he said ‘no later than ten’. I must admit I find it odd that I essentially act as a chaperone for my older brother on these excursions. By eleven he’s usually unable to walk in a straight line but insists that he can still drink two drinks at once and flirt with the bartender.

                I hope your schedule allows for you to get a good night’s sleep and your Monday mornings are nice and relaxing. I will have to make an effort to be more diligent in the future when my brother suggests celebratory drinks on a Sunday night.

Sincerely,

Thursday
(which, coincidentally, is my favourite day of the week, for reasons I may reveal at a later date)

---          

Dean laughed, imagining Thursday’s fabled older brother trying to juggle two drinks and a bartender, but he was sympathetic of his friend’s horrible Monday, having had a few of those himself. Mind, those were most often his own doing, so he couldn’t complain too much.

He wondered briefly what was so special about Thursdays as he began typing a reply.

---

To                                 Subject
angelofthursday@...      (no subject)

                Wow. How are you alive right now? Sorry to hear that you’re not a fan of Mondays. It’s actually the one day a week I get to sleep in. I wonder if that was a subconscious decision based on years of hating Monday mornings like yourself. That sounds like something my genius little brother would say.

Since I get to make my own schedule I force myself to take the early shifts. Gives me more time in the evenings to do other stuff, since I usually end up working seven day weeks. So yeah, Mondays are pretty good for me. But look on the bright side, at least you get weekends.

Actually, this weekend I’m taking a couple days off to take my Baby upstate and visit my brother. Can’t even tell you how much I’m looking forward to that. Finally, I can drive somewhere.

Hope the rest of your day doesn’t suck.

-Zeppelin

---

With a content smirk, he hit send and downed the rest of his coffee. The clock above the TV read just past eight. Dean sighed and pushed himself off the couch. He returned to the kitchen and popped two slices of bread into the toaster before shambling off to his room to get dressed. If he was up, he may as well go in to work.

*

Book Haven, a used-and-new bookstore with a gorgeous old, painted facade and a huge display window, had been owned by his mother’s family for two generations before it was passed on to Mary. By that time she had already met John, and the two had been dating for quite some time. Her father hadn’t been overly fond of his daughter’s choice for a husband and he didn’t exactly keep quiet about it, so Mary had planned on eloping with John, getting far away from New York and living simple in the country somewhere.

That plan never came to be. The very night they had decided to run, both of Mary’s parents were killed in a disastrous home invasion. Compelled by grief and guilt, Mary took over the store, John took a job as a mechanic in the heart of the city, and they made do.

A decade later, they had two young boys, and the city had grown. The bookstore did remarkably well under Mary’s ownership, even better than in previous years, due in no small part to her warmth and ability to connect with every one of her customers.

As soon as Dean could reach the counter, he started helping his mom out on weekends – dusting shelves, sweeping the entrance, occasionally keeping customers’ kids entertained. He loved it and had always looked forward to the day when he’d be running the place. However, he didn’t expect it to happen quite as soon as it did.

Mary fell irreparably ill five years ago, and Dean took over. It was another hard, long year before she finally succumbed to her illness and was able to be at rest. Once word got around, the turnout at the store was overwhelming. People came from all over the city to offer their condolences and Dean found that he had to excuse himself and rush to the back room to avoid breaking down in public on more than one occasion that week. Sam had even taken a semester off from university at Stanford to help out at the store and at home, knowing full well that his brother was in no fit state to handle it all alone.

Their father didn’t take Mary’s death well, and spent months subsequent with a bottle in his hand. Sam would hide the car keys, which always led to a fight, which led to John storming out of the house and walking off down the street to the nearest bar.

One night Sam was out late and forgot to hide the keys, and John drove the Impala into a lamp post. He wasn’t wearing his seatbelt and was thrown through the windshield. By some miracle, he survived. John had been in the hospital for months, recovering from broken ribs, a broken clavicle, broken leg, broken arm... He never touched the drink after that.

While John was in the hospital, Dean had channelled all his frustration and worry into fixing up the car and when his dad was finally able to go home, Dean picked him up in the newly refurbished beauty and he swore he saw tears in his father’s eyes. John decided right then and there that Dean deserved the classic car more than he did.

If only Dean had more chances to drive her. Bi-monthly journeys upstate to visit Sam, and a yearly pilgrimage out to South Dakota to spend Thanksgiving with John, who was now retired and living in a nice big cabin on a lake, were not enough to sate him. There was an ever-present itch to get his hands on the steering wheel and his foot on the accelerator.

He stepped out of the subway station and onto the bright sunlit street. He was lucky to work so close to the station, especially in February when the city was cold and rainy more often than not. But on rare days like this, when the sun was shining and the air was crisp, with the promise of spring in a few short weeks, he didn’t mind the walk. It sure beat trying to shield oneself from diagonal rain with an umbrella that’s being whipped six directions in gale force winds.

He was reminded of something Thursday had mentioned a couple weeks back about the inevitability of rain the one day he forgot to bring an umbrella and cringed. The forecast hadn’t called for rain until tomorrow evening, but he hoped the sun would at least stick around long enough for him to get home.

He rounded the corner and spotted Charlie, perched on the back of a bus stop bench in front of the large display window, already waiting for him. Dean had shot her a quick text before leaving to let her know he was coming in early after all, but hadn’t expected her to show up until eleven. He could have easily handled the store on his own for a couple hours.

As he approached, she hopped off the bench, clutching her warm, grey wool coat tightly around her. “Morning, boss.”

“Charlie,” Dean nodded, happy to see her despite his confusion, “you didn’t have to come in early.”

Charlie shook her head, “It’s cool, Kevin’s already covering for me later anyway.” She winked conspiratorially, “Date night.”

“Ah, gotcha,” Dean nodded again, turning to hide a fond smile as he unlocked the old door and let them in. “And how is Gilda?”

While they went about setting up shop, Charlie launched into a dramatic story about how some drunken sleaze-ball was hitting on her girlfriend last night while Gilda was tending bar at some swanky club downtown.

Dean has known Charlie long enough to know that this is quite a regular occurrence, and that despite the number of times Gilda has told her there’s nothing to be worried about, Charlie still worries. Not that some drunken sleaze-ball is going to steal her girl, but that one day, one drunken sleaze-ball won’t take no for an answer. Gilda often works the late, late shifts, trying to fit a second job around her class schedule to cover expenses, and Charlie confided in Dean that she’s spent many a night lying awake, wondering if she’s all right.

“At least she’s almost finished grad school,” Charlie paused by the front of the store, staring wistfully out the window. “Soon she’ll be a school counsellor and the only thing I’ll have to worry about is what we’re going to do with all the extra time.” That set her mind down a completely different path and her expression shifted from concerned to intrigued.

“Charlie.” Dean snapped his fingers and she jolted out of whatever fantasy evening she was plotting in her head. He crossed the room to grab a stack of Young Readers novels and tousled her red hair on the way. “Gilda’s a tough girl, she can hold her own. A few harmless drunk dudes aren’t worth stressing yourself out over.”

“Yeah, you’re probably right.” She sighed deeply and took another stack from the counter. “So,” she began with a devious glint in her eye, “get any more e-mails from your mystery man lately?”

She grinned when his ears turned pink and he turned away from her to needlessly organize the self help books.

Charlie was the only one who knew about his regular correspondence with Thursday. The only reason she knew the whole story was because she had been at his apartment last week helping him fix his e-mail server which had gone awry. Once she had it up and running, three new e-mails from Thursday had popped into his inbox. Her curiosity and desire to know everything were no match for Dean’s weak attempts to brush it off, and honestly, it had been a bit of a relief to finally tell someone.

It felt less like a dirty little secret after that. He still hadn’t told Sam, for fear that he would get weird about it or make a big deal out of nothing. Like Charlie was doing now.

“This morning, now drop it.” He said edgily, stalking off toward the back room while Charlie’s giggles pervaded the small sales floor.

*

They opened their doors promptly at 9:30am and the first few regulars floated in. Dean greeted them all by name and set about helping them find what they were after while Charlie worked the till and changed out the books from the window display.

Around eleven, Chuck ambled in, coffee in hand, looking harried and like he hadn’t slept in a week. He mumbled a quick greeting and headed to the back. Dean exchanged a significant look with Charlie and they both shrugged.

A few minutes later, Chuck appeared through the half-curtain that hung in the narrow archway that separated the back room from the sales floor. He nodded politely to a few of their regular customers who looked a bit taken aback by his rather dishevelled appearance, and approached the front counter.

When he noticed the twin questioning looks Dean and Charlie were casting at him, he held up one hand in an attempt to stave them off. “Don’t even ask.”

They didn’t stop staring, so he added with a disdainful sigh, “My editor has been giving me hell because I haven’t sent her anything in weeks.”

Dean nodded, but in keeping with his role as owner and operator of the store, felt he needed to mention one thing. “Chuck, your shirt is inside out.”

He heard Charlie stifle a laugh as she pretended to be very busy with the display. Chuck inspected his shirt and, heaving another dramatic sigh, disappeared into the back room to fix it.

Dean shook his head, matching Charlie’s grin when she turned to exchange another knowing glance. He’s only known her for the better part of a year, but she had quickly become one of his best friends.

The 23-year-old had applied for a job last spring after Garth, one of many college kids that Dean often hired during semester breaks and big seasonal rushes, tendered his resignation with plans to travel south for school. The “now hiring” sign hadn’t been in the window ten minutes when Charlie came in to the store to drop off her resume. Dean had given her a brief interview and hired her then and there.

There was something about her. He couldn’t quite put his finger on it, but it was like they’d known each other for years. Their working relationship was a breeze, and it made way for an equally easy personal relationship outside of the office. By the Fourth of July, Charlie was practically part of the family.

Dean had always been a bit of a sci-fi nerd, but thanks to Charlie he had far more opportunities to fully express his nerdiness, and even add to it, as she insisted on dragging him to D&D meets every Wednesday night.

Charlie was easily one of the best friends he ever had, but he was good friends with the rest of his staff as well.

Chuck Shurley had been working there long before Dean took over. He was a relatively unknown local author, working at the store for some extra income between royalty cheques. He was generally mild-mannered, jumpy, and kept to himself, but he knew more about books and the publishing business than anyone who had ever worked at Book Haven and was an asset to the store. Chuck had helped a great deal when Mary passed away, even going so far as to stay hours after closing for free to make sure everything would run smoothly for Dean in the morning. He was almost always at the Winchesters’ table for Thanksgiving.

Kevin Tran, a genius-level kid with a perfect GPA and a penchant for numbers, worked the books. Dean was never very good at the accounting, and he hated sitting at the tiny desk in the back crunching numbers long after the store had closed, so he placed an ad in a few newspapers looking for someone to balance the books. A few days with no response and things were looking bleak, when a primly-dressed 17-year-old Asian kid carrying a cello case and a newspaper showed up claiming to be the answer to all Dean’s prayers. Turns out he was. Kevin was incredible. He not only revolutionized their accounting system, but he also began helping out in other ways around the store; arranging shelves to maximize profits, giving Dean a breakdown of the best sellers of each quarter and which sales patterns tended to form and when, even reorganizing the break room in a more convenient and comfortable way. Now he’s completing his final year of high school and works four evenings a week. He gets most of the accounting done in the first hour or so of his shift and spends the rest of the time helping Charlie or Chuck out front.

Long story short, Dean was incredibly lucky. Everyone got along famously and he couldn’t be happier with the little group he had managed to pull together.

He leaned against the counter, arms folded across his chest as he took in the scenery; a mother and her young son flipped through children’s books while two young women scoured the well-read novels in the used section. Nearest to the back room, Charlie was absently flipping through the new issue of Deadpool as Chuck nattered away to an older man about how Stephen King is a national treasure.

Doesn’t get much better than this, he mused as he pushed away from the counter to greet Mr. and Mrs. Carrigan, an elderly couple who had been regulars at Book Haven for years and had just walked through the door.