Amor Litteras - Part One
Title: Amor Litteras
Author: menofsweaters and moosetaches
Artist: saffron_zephyr
Pairing: Sam/Gabriel, Dean/Castiel, unrequited Sam/Lucifer, Lucifer/Michael if you squint
Rating: PG-13 for language and some sexual references
Warnings: None, unless any of the above pairings squick you out. It’s pretty tame.
Word Count: 19,377
Summary: Sam has been waiting for the Cherubim to match him up with his true love his entire life, but so far, he's had no luck. While Dean fully intends to stay a free-wheeling bachelor forever, Sam is desperate to find a match before his time runs out. When his brother is paired with an unlikely angel named Castiel, Sam is thrown head-first into a world of archangels, love letters, and an alarming amount of vests. However, as he gets closer to a particularly charming archangel named Gabriel, he starts to doubt the system. Hijinks include Gabriel in sock hop garb, spying on Dean and Cas, way too chipper Samandriel, creeper!Michael, and Gabriel and Lucifer fighting over Sam's pretty face (sort of).
Link to full fic: AO3
Link to art masterpost: LJ
Sam was scowling as he watched Dean stick a thumb tack viciously through the red envelope, pinning it to the wall with all of the others. Dean smirked at it like it was a trophy he’d stolen from a twelve-year-old.
“What d’ya think, Sammy?” Dean asked jovially, turning to grin at his brother.
“I think it’s sick,” Sammy replied. “You are sick. There is something wrong with you.”
“Hey, if there’s something wrong with me, then there’s something wrong with you.” Dean brushed past him, still grinning, on his way into the kitchen. Sam rolled his eyes.
“I just don’t understand why you do this. Normal people don’t do this.”
“Hey, any red-blooded guy would be proud to show that he’s not tied down to some chick,” Dean insisted, pulling the refrigerator door open and peering at its contents. “I’m just glad it’s almost over,” he continued, grabbing the ingredients for what would most likely be a massive abomination of a sandwich.
“You know, you can opt out of the pool,” Sam pointed out.
“Where’s the fun in that?” He gestured to the nine red envelopes pinned and taped to the wall of their apartment, all in various states of disrepair. “I came, I saw, I conquered, dude. Even angels can’t keep me down. The whole destiny thing is bullshit, anyway.” Dean pulled several slices of bread out and laid them on the counter. He almost offered Sam a sandwich, too, but his brother was giving him that weird, angry constipated face again, so he decided against it. Sam could make his own damn lunch.
“That bullshit is how Mom and Dad got together, Dean.” Sam sighed heavily and practically collapsed into one of the chairs in their small dining room, restlessly straightening his tie. “I get that you don’t want that for yourself, I just don’t -- “ He snapped his mouth shut and looked away.
Sam could see the guilt immediately apparent on Dean’s face. Sam knew his brother hadn’t meant to flaunt what he had right in front of him. Dean knew, everyone knew, for goodness’ sake, that Sam was into it -- the whole idea of fate, of winged cherubs choosing some perfect soulmate for everyone. Dean just didn’t buy it. Hell, Dean could probably be single forever and stay at least somewhat happy as long as he got laid now and then. Ever since Dean had gotten that first letter, that first name -- and damn if that hadn’t ended spectacularly -- it had become a kind of game. A way to outsmart the system. The cupid brigade insisted that they could find the perfect match for anyone, and Sam knew his brother was determined to prove them wrong. Once Dean got that tenth letter, the tenth match, and that one failed like all the others... Well, then the angels would have to admit that they were wrong, and put it on some official documentation to prove it, too. Once that happened, he’d win the game.
Sam didn’t see it as some stupid game, though, and he could tell that Dean sort of pitied him for it. Whereas Dean waited for the next letter so that he could continue his mission of sexual conquest, Sam waited for the naive idea that a piece of paper from a bunch of douchebags with wings would help him find his True Love. And he’d been waiting for twelve years. If they kept him waiting, if Sam’s thirtieth birthday rolled around and he still hadn’t gotten a letter, that was it. They took him out of the pool. Labelled him as “unmatchable.” It was sad, it was terrifying, and, according to Dean, really, really stupid.
“Hey, listen,” Dean grumbled. “I didn’t mean to, ya know, make you feel bad or anything. I mean, the whole system’s fucked. You shouldn’t let it bother you.”
“Easy for you to say.” Sam was pouting at the kitchen table, sifting through the bills and junk mail left there.
“Look, you’re a good-looking guy -- I mean, you gotta be, you’re related to me -- “ Dean gave his brother a smug look. “You’ve got a job and a car and you’re not a complete moron. Just go find a date on your own.” Sam mumbled something incoherent and Dean shrugged in defeat. It was the same argument they always had. Sam was depressed the cupids hadn’t stuck him with one of their little arrows, Dean told him to find a girlfriend on his own, Sam stubbornly refused. He knew why. Dean glanced up at one of the photographs of their parents on the wall. It was taken when they were younger, and they were kissing with silly smiles on their faces. Mary was wearing a blue dress.
Yeah, Dean got why Sam acted this way. He just didn’t know what to do about it any more.
“Come on,” he grumbled. “We’d better get going. I know those seraphim tightwads like to keep you on a short leash.” Sam opened his mouth to say something scathing, but seemed to think better of it.
“Jerk,” he muttered, grabbing his briefcase as Dean attempted to shove the giant sandwich he’d spawned into a paper bag.
“Bitch.”
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The Winchester brothers had a system. Dean worked with the Watcher Division, looking out for the safety of the citizens. It was a joint venture between the angels there and humans, dedicated to protecting the populace from criminals and monsters. It was perfect for Dean, and the main office was just blocks away from the Seraphim, which was convenient for his brother.
Sam had worked for the Seraphim ever since he got out of school. They were the foremost governing body of their world, taking charge of creating the laws as well as upholding them. He guessed you could call it a dream. He was still working to help people, but more on the legal side of things. He preferred it that way. Dean pulled up in front of the Authority complex, buildings grey and ominous, and Sam jumped out, the same as every morning.
“Take care, Sammy,” Dean said with a little wave, pulling back out into traffic towards the Watcher building. Sam shoved his hands in his pockets and strolled towards his office.
He passed the smallest of the three buildings along the street, home of the Malakim envoy, all smooth concrete reaching up into the sky, adorned only with the winged crest of the Malakim. Then there was the Cherubim building, with its glittering glass dome and elegant columns. Three statues stood out front: an eagle, an ox, and a man. It was a somewhat foreboding building for such a romantic purpose. Sam felt like it was mocking him. Finally, he came to his building. It looked much like a gigantic courthouse, with an open green lawn stretching out in front. It was slightly cold, but it was familiar. Sam couldn’t help but smile to himself.
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Sam liked his job, but he was glad he had the weekend ahead of him. He loosened his tie and sat heavily in his armchair. The leather creaked as he shifted in place and Sam searched for the TV remote on the messy table next to him. How Dean managed to create so much clutter was a mystery that had haunted Sam for nearly three decades. He was just about to give up his hunt when the doorbell rang.
He swung the door open to reveal a kid who couldn’t have been more than sixteen wearing a red striped uniform and a big smile.
“Greetings on this beautiful day, sir,” he chirped, completely oblivious to the overcast skies behind him. “I’m with the Cherubim, my name is Samandriel.” Sam brightened at the introduction.
“Hey! My name is Sam, too.” Samandriel was positively delighted out of his pants by the news.
“Isn’t that swell? The world is full of happy coincidences.” Sam sometimes wondered if the Cherubim were on some kind of stimulant. Coffee, soda, cocaine, maybe meth.
“How can I help you, Samandriel?”
“Gosh you’re so kind, I have a letter here for someone very special,” Samandriel teased in a sing-song voice and pulled out a red envelope from his messenger bag. “Is there a Dean Winchester residing at this address?”
Sam’s face fell. Of course, what else had he fucking expected? He snatched the envelope from the cherub’s hand and slammed the door in his face just as Samandriel reminded him to have a delightful day.
Dean thought it was funnier than hell when he got home a few hours later.
“Damn, you kidding me? I just got one of these a week ago. They must want me out of the pool fast. Can’t believe you gave that kid a hard time.”
Sam frowned and muttered, “He’ll be fine, you know how they are. He probably thought a strong wind came through the apartment and shut the door accidentally.”
Dean hummed in agreement and tore open the envelope with no finesse and read the letter inside as he fished a few Cheetos out of the bag on the coffee table. He laughed obnoxiously and Sam kind of wanted to strangle him.
“It’s another angel, guess I haven’t defiled enough of them. Well, not that she was--” Dean cleared his throat. “Chick’s name is Castiel. Get this: she works in the accounting department for the Cherubim. I didn’t even know they needed accountants. I bet she’s a sexy librarian type, all brainy with glasses. Might as well go out on a good note.”
“Are you sure Castiel is a woman? She has one of those angel gender neutral names.” Sam only asked because it was a common mistake to make. Dean shrugged.
“Okay, so maybe he’s a sexy librarian in a sweater vest. Either way, totally my type.”
Sam rolled his eyes. Everybody was Dean’s type. He rubbed his forehead in exasperation.
“I just can’t believe this, you just broke up with that Carmen or whatever.” Dean shrugged.
“Them’s the breaks, kid.”
Sam couldn’t handle his brother and stormed off to his room like he was a teenager again.
“Oh, come on, Sammy. Don’t be sore!” He followed after Sam, waving his letter around. “There’s all this extra crap written here, I need you to sort through the legalese for me.”
“Figure it out for yourself, I’ve got a headache.”
“Sammy, Saaaammy. Please?”
Sam turned on his heels and took the letter from Dean to shut him up. He scanned the paper and frowned.
“It basically says you need to meet this Castiel at the Cherubim headquarters before any ‘informal meetings,’ I guess they mean dates.” He pointedly ignored Dean’s smug noises. “It’s a very old fashioned thing. I’ve never actually heard of anyone doing it in this century.”
“Great, old fashioned. Prude more like.”
“Well, I guess it means you’ve got to go to the Cherubim office tomorrow.” Dean made a face like he’d eaten something unpleasant.
“Ugh, I don’t want to go there. Sounds stuffy. Hey I know! Why don’t you tag along, Sam? I know you’ve always had a hankering to go in there. Who knows, maybe you can bribe one of the cupid guys to hook you up with a swimsuit model or something.”
“I don’t think it works that way, Dean.”
“Lighten up, Sam. Come on, come with me. It’ll be fun.” Sam worried his bottom lip.
“You just said you didn’t want to go, why is it fun all of a sudden?”
“I don’t know, brotherly bonding or some crap. Just go with me, I promise I’ll get you some of that spinach salad you like at the Roadhouse later. Hey you like that.”
“Fine,” Sam shook his head, “it just better not take too long.”
“Never takes too long with me, Sammy, if you know what I mean.” Dean cocked an eyebrow and smirked. Sam sighed heavily. His brother was difficult to deal with sometimes, but he was genuinely curious about the inner workings of the Cherubim Headquarters. Maybe he could find somebody and ask about his fate and if he’d be getting a letter anytime soon. Perhaps there was a clerical error. That would explain everything.
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“Well, it’s clean,” Dean said. It was a vast understatement; the inside of Cherubim Headquarters was blindingly white with hyper-polished marble floors and columns which supported the nose-bleed high ceiling. A tiny metal plaque proclaimed it to be called the Solomon Building. It smelled antiseptic and Sam was pretty sure it would be safe to perform surgery in here.
“The angels at my precinct are total slobs. So, are we like the only ones here?” Dean’s voice echoed through the foyer, “Hello?”
Sam had always been, well, not awestruck exactly, but definitely intrigued by the angels. It was probably a big part of the reason he’d always wanted to work with the Seraphim. He was also, predictably, puzzled by them. Angels as a whole seemed to have a somewhat unsteady grasp on How to Interact with Humans 101, but some were definitely better than others. While the Watchers at Dean’s precinct were boisterous, the angels at Sam’s office were cold; while the Malakim were always sharp and intense, the Cherubim were undoubtedly chipper. One thing they all shared was a certain drive and a decidedly inhuman air.
He thought of Samandriel and winced inwardly at his earlier behavior. He was having a hard time imagining such a sweet kid in such a cold facility when a familiar voice rang out.
“Sam?” Samandriel had just freaking appeared, like angels were prone to do, and was grinning from ear to ear. “Well fancy seeing you again! It’s me -- Samandriel!”
“Yeah, I, uh, remember you,” Sam mumbled. Samandriel looked like he might faint from joy.
“Well, I’m here for a Dean Winchester,” he chirped, holding up a piece of paper. “That’s not you, is it?”
“No, that’s my brother. I’m Sam, remember? You literally just called me by my name.” Samandriel just shrugged.
“You never know! I don’t like to make assumptions. It could be your middle name, or a nickname!”
“Why would my nickname be my brother’s name?”
“Nicknames are funny that way. Sometimes folks call me Alfie and I have no idea why!” Sam stared, perplexed, then pointed to a spot behind the angel.
“He’s over there.”
Samandriel proceeded to lead Dean up a large staircase, jabbering about how exciting it all was, with no apparent need or desire to breathe. Dean’s face was flashing between irritation, confusion, and something that might have been fear.
Sam sighed and resigned himself to waiting. Peering around at the polished marble, he couldn’t help wondering where the letters came in and went out. He peeked around the corner. If he could just see his file, maybe it would all make sense...
“You lost?”
Sam whipped around and found himself staring down at a stranger wearing a green jacket and a self-confident smirk. He didn’t look particularly like an angel, but Sam guessed he must be one from the way he’d appeared out of thin air. He had an open, mischievous sort of grin, and Sam found himself unable to explain his mediocre snooping.
“I, uh,” he stammered.
“I’m sure you’re used to clearing tall buildings in a single leap, but this place can be a maze. Want a tour?” the angel asked, unfazed. Sam blinked. He couldn’t think of why not.
“Sure, I guess,” he blurted out, sounding a little more eager than he’d intended. “That is, if you’ve got the time.”
“For you, kiddo? I’ve got all the time in the world. Gabe.” He held out his hand and Sam grasped it automatically. He wondered if there was a good way to ask about his file, a way to bring up his complete and utter lack of romantic potential, without sounding too desperate. Maybe he didn’t care if he sounded desperate -- he was desperate. This angel dude could be the answer to his problem.
“I’ve been known to render people speechless now and then,” a warm voice cut through his inner monologue, “but usually this is the part where you tell me your name.” Sam flushed and jerked his hand out of the guy’s -- Gabe’s -- grip.
“Sorry,” he muttered. “Just out of it, I guess. Sam. Sam Winchester. I work over with the Seraphim.” Gabe’s eyebrows jumped up.
“Cripes, you’re with legal? This isn’t an inspection, is it?” he teased. “Here to shut us down for good? I know how you lawyer types hate fun and love and basically everything beautiful in the world.” Sam couldn’t help but laugh.
“No, just visiting.”
“Promise?”
“Promise.”
“I guess I can trust you then. You’ve got one of those faces. Come on, Sammy, let me show you the wonderful world of the Cherubim! I can arrange for some Oompa-Lumpas if you’d like.”
“Uh, no, that’s really okay.”
“Your loss.”
Gabe proceeded to drag him around the foyer, pointing out ancient sculptures and paintings and proclaiming most of the artists to be either douchebags or passably attractive. He didn’t mention anything about letters or files, though. Sam found himself wondering exactly what he’d gotten himself into when they began scaling the staircase he’d seen Dean go up. He surreptitiously glanced around, looking for something that might have been a file room while Gabe blathered on beside him.
“--And that’s where I drank Camael under the table. I guess that whole flaming sword thing was to save face. What a lightweight. And over there’s where I made it with Himeros. I wouldn’t recommend it, he’s all tongue. Are you even listening? This is some important history here, buddy.”
“Oh, um, yeah! Sorry.” Gabe narrowed his eyes.
“No one seriously comes to cupid HQ for a tour of the facilities. Or listens to me for that long. What are you really here for?”
“Well, I came here with my brother. Some kind of meeting.”
“Yeah? And what else?”
Sam felt his face go hot. Suddenly his missing letter problem seemed frivolous, juvenile. Definitely not something he wanted to talk about with a stranger -- even a chatty, easygoing stranger with a nice ass. Scratch that last part. He’d sworn off dating for the time being. But Gabe was staring at him with an earnest, piercing gaze, head slightly tilted, waiting for an answer.
“Well,” Sam heard himself say, “there is -- ”
“Sam!” Samandriel’s now-familiar voice cut through the conversation. The angel beckoned them forward. “And Gabriel! It’s such an honor to see you again, sir.” He looked a little tongue-tied and Sam wondered exactly what Gabe did, or Gabriel, apparently... it must be a popular angel name, like Jessica. Or David. Whatever.
“Come on, it’s time for the formal meeting. This will be so wonderful!” Samandriel got a far-off, starry-eyed look that Sam pointedly ignored.
“Wait a second,” Gabe began, looking at Sam sideways. “You said Winchester, right? Are you the one that’s unlucky enough to be matched with my brother? Say it ain’t so.”
“Uh, no, it ain’t so,” Sam mumbled. “That’s my brother, Dean. So you’re... Castiel’s brother? I mean, I guess all angels are brothers, aren’t they?” Gabe shrugged.
“Sort of? It’s complicated. More of a brotherly bond, not so much by blood, though I do have some of those.”
“Huh?”
“Brothers. Like real brothers. Three of ‘em. Pain in my ass.”
“And this Castiel is one of them?” Sam made a mental note that he had been totally right, Castiel was a dude. Not that Dean would mind, despite his macho attitude.
“Nah, Cassie’s just special.” Gabe shoved his hands in his pockets and chuckled. “Heh. My brother is gonna bone your brother.” He winced. “Well, more realistically, not bone. Actually, I feel kinda bad for your brother. What’s his name again?”
“Dean,” Sam grumbled. Dean, Dean, Dean. That’s all anyone ever wanted to talk about.
“My condolences to Dean.” Gabriel straightened up and slapped Sam on the back as Samandriel led them into a meeting room. “Time to play chaperone, Sammy.”
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The room was pretty unremarkable, like any small office. Although hopefully most offices were devoid of Sam’s brother standing in the middle of them glaring at some equally sore guy in a trench coat. Sam couldn’t leave Dean alone for ten minutes before he managed to piss someone off. Samandriel was standing between the pair, beaming like there was no other place he’d rather be than the center of an angry alpha male sandwich.
“Sam, you’ve finally arrived and Gabriel, sir!” Samandriel vibrated with excitement. Sam tried to catch Dean’s attention, but he was too busy boring a hole into mystery trench coat guy’s face. Gabriel leaned over to whisper to the human.
“Your brother makes friends fast.”
“Yeah... Is that Castiel?” Gabriel rolled his eyes.
“I hope your brother doesn’t like having fun.”
Samandriel cleared his throat and spoke, “Now that we’ve gathered it’s time to proceed. This is my first time doing this, so sorry for any mistakes!”
“You got promoted, huh?” Sam asked, trying to relieve some of the lingering awkwardness he felt about the young angel. Samandriel glowed, but Castiel interjected with a voice blues singers would envy.
“He is the only one who wanted to do it. Everyone else was busy.”
“It’s an honor,” Samandriel squeaked pleasantly. “Now are you Dean Winchester? And you, Castiel, Angel of the Lord?”
“Yes,” they spoke simultaneously in matching harsh tones.
“And you, Samuel Winchester and Gabriel, brother to Castiel have witnessed the meeting of this pair matched by the divine grace of Heaven?”
Sam and Gabriel agreed. It felt weirdly like they were attending a shotgun wedding. Samandriel clapped his hands.
“Then it is done! It is strongly encourage that the matched pair go on an unchaperoned outing together,” Samandriel spoke in a stage whisper as though such a concept was scandalous in the 21st century. Dean huffed and finally tore his gaze from the rigid angel.
Castiel spoke woodenly, “I know a place we can go. I must fetch an item from my office, but I will promptly return to escort you.” Before Dean could agree, Castiel vanished on the spot.
“What happened between you two?” Sam asked, Dean crossed his arms and glared darkly.
“I don’t want to talk about it.”
“Castiel is in accounting, he’s not a people person.” Gabriel shrugged. Sam furrowed his brow.
“What do angels need an accounting department for?”
Gabriel just gave Sam an expression that read, ‘why do you think, Dumbo?’ Then Castiel reappeared next to Dean who nearly jumped out of his skin and cursed loudly. Castiel watched his display apathetically and when Dean’s rant was finished, he requested that the human follow him. Dean obviously wanted to do the exact opposite of whatever Castiel told him, but marched after him out of the office with a gruff goodbye to Sam.
Sam watched his brother leave and looked back to see Samandriel smiling dopily at him and Gabriel like he had been for the past five minutes. Sam spoke quietly so only Gabriel could hear him.
“Is he alright? He kind of comes off like he’s been lobotomized.”
“Well, he did used to work with Naomi, but he’s just, uh, chipper.” Gabriel then spoke at full volume, “Good job, Alfie. Go see if someone needs help… somewhere. I don’t know, just figure it out.”
Samandriel saluted and disappeared. Angels were fairly weird, Sam decided. Watching Castiel and Dean leave for their (probably super awkward) lunch date, Sam felt his shoulders slump downwards in a mix of jealousy and resignation.
“So how do I get out of here?” he grumbled.
“Leaving so soon? We were in the middle of an important conversation about my sexual conquests and your super secret desire to be a cherub or something.” Gabe snapped his fingers and coffee appeared in Sam’s hand, warm and tempting through the paper cup. Gabe sipped on his own magical angel coffee, which was topped with a generous mound of whipped cream.
“You were going to tell me something?” he prompted. Sam looked down and shuffled his feet, which was ridiculous, because he hadn’t shuffled his feet in embarrassment since high school. He was a grown man, dammit! He reminded himself that this was business -- Gabe worked here, and was some kind of big shot too, so it was his responsibility to help, right?
“Come on, spill,” Gabe urged. “Unhappy with your supermodel match? Looking for more of a sexy nurse type? Because that can be arranged.” He waggled his eyebrows, which definitely did not make Sam almost spit out his coffee.
“No, no, kind of the opposite, actually,” he admitted.
“Been a while between letters? I wouldn’t worry. Sometimes the celestial matchmaking service is a little slower than you’d like.”
“No, it’s that... well, I’m almost 30 and I-I’ve never gotten a letter.” Gabe actually looked shocked for a moment.
“Seriously? Never?” Sam shook his head, defeated.
“Wow. I mean... wow. The Almighty really dropped the ball on that one. That’s a bummer, Sam.”
“I was actually hoping to, I dunno, check out my file or something. Make sure there’s nothing... wrong. Out of the ordinary.”
“No one gets access to their own file, Sam,” Gabriel sighed. “Not even angels.”
“That makes sense.” Sam tried not to seem too disappointed, but Gabe’s sidelong glances were surprisingly observant.
“But I could check on your file, if you’d like. Make sure you’re not labelled as a serial killer. You’re not one, right?”
“No!” Sam laughed. “I’m not. I swear.”
“That’s just what a serial killer would say. But I’ve got a soft spot for lonely murderers. I’ll take a look.” He glanced at an elaborate clock on the wall that was probably older than Sam. Two Sams. Maybe three. “Who knows how long our idiot brothers will be. What say you wait right here, I’ll nab your file, and we can grab lunch?” Gabriel flashed a rather blindingly charming smile and Sam fought against the urge to roll his eyes. He wasn’t stupid. He knew what Gabe was up to, and it was a decent excuse for a date. He’d promised himself no dating until the big 3-0, but he couldn’t see the harm in a simple lunch.
“Yeah, okay,” he finally agreed. “Sounds great. I really appreciate it.”
“No sweat, kiddo,” Gabe replied brightly, rocking back on his heels. “Just stay put. I’ll make sure your file is spick ‘n span.”
“You, uh, must be a big shot around here if you can just poke around in people’s files,” he chuckled. “You’re Samandriel’s boss, right? Someone needs to stop giving that kid stimulants.”
“You could say that,” Gabriel hummed. Sam rose an eyebrow.
“What are you, the CFO?”
“We’re angels/i>
“You have accountants,” Sam pointed out.
“We have accounts.”
“So... what? You’re the president? The head honcho? The final boss?”
“I’m kind of everyone’s boss. Well, everyone here.”
“Are we talking everyone in this office or everyone on this floor or...?”
“More like everyone in this building. And a few others, I think.” Sam gaped.
“Wait, wait. Your name is Gabriel.”
“Don’t wear it out. Or do. But I’d prefer that under different circumstances, like screaming circumstances.”
“But not like... the Gabriel, right? It’s gotta be a popular angel name.”
“Um, Sam? There are no ‘popular’ angel games. We’re all one of a kind.”
“But... the Gabriel is an archangel!” Gabe spread his hands wide.
“You caught me. So, lunch? I’m thinking Thai.”
“I can’t go to lunch with you! You’re an archangel!”
“Ah, ah, ah,” Gabriel waggled his finger, “you already agreed. We have a verbal contract. No take-backsies. See you in a jiffy, Sam.” With that, he winked obnoxiously and disappeared, leaving Sam to mull over exactly what he’d gotten himself into.
After five minutes of having a nervous breakdown over the fact that he was going on a date (just lunch Winchester, pull yourself together) with an archangel (it’s just a title, meaningless really, and you’re taller anyway) which felt like an eternity, Gabe reappeared. Sam tried not to jump or clutch his pearls like a distressed southern belle.
“Miss me?” Gabe said with a smirk, holding up a file folder triumphantly. It wasn’t very impressive, really. Sam was vaguely disappointed. Just a thin file folder, white, with a slight silvery sheen. He could see there were papers inside -- chronicles of his life, maybe? His sexual history? His last physical? There was no way to tell, short of snatching it away from an archangel.
“No peeking, Sam,” Gabriel tutted, as though he could read Sam’s mind. Maybe he could. Without warning, Gabe reached up and pressed fingertips to Sam’s forehead, and suddenly he had the awful, exhilarating sensation of his brain being sucked out through his pants pockets and rearranged into a tasteful bouquet. Being angel-teleported was an experience he’d had a few times before, usually when his angelic coworkers were impatient with mundane travel arrangements, but he got the feeling that Gabriel had a little more... juice. It left his skin tingling and the usual nausea subsided almost instantly.
They were in a small restaurant packed with brightly colored tables and chairs and the the air was permeated with the smell of peanut sauce and hot chiles. The angel dragged him to a table in the corner. An unimpressed-looking waitress soon approached.
“The Archangel Gabriel,” she greeted monotonously. “As I live and breathe.” She wasted no time and placed some creamy iced beverage in front of him, then looked at Sam expectantly.
“Thai iced tea?” Gabe offered, shoving the glass in Sam’s face. Sam tentatively took a sip, then grimaced.
“Wow, that’s,” he choked a little, “really sweet. I’ll just have water, thanks.” Gabriel looked disappointed, then proceeded to order some kind of elaborate noodle dish that involved fish balls and made the waitress’ scowl deepen. Sam chose a salad.
Gabriel leaned back in his chair and flipped through Sam’s file, brow furrowed, as they waited for their food. His eyes flicked sharply across the paper and Sam fidgeted nervously. That file undoubtedly had some very intimate information in it, and watching Gabe read it was understandably nerve-wracking.
“I hate to break it to you, kiddo,” he began, “but there’s nothing wrong with your file. Everything’s in order. I honestly don’t know why you’ve never been matched.” He sounded apologetic, but there was no pity in his voice, which Sam was thankful for. “That’s heavenly Bachelorette for you. Take it from me, you don’t need the Almighty to hook you up with anyone.”
“That’s not--” Sam bit his tongue as their food arrived. He didn’t want to snap at Gabriel, or spill his guts about why he wanted that letter so badly. He sighed in resignation. “Thanks anyway. I appreciate it, really.”
Gabe gave him a lopsided smile and started attacking his noodles with obvious fervor, despite his lack of need for sustenance. After his discouragement subsided, Sam was surprised to find that he was having a good time. Gabriel was charismatic and joyful, brimming with anecdotes about angels and demons and demigods. He laughed too loud and couldn’t go five minutes without making a raunchy comment. Sam found that he didn’t mind, though, because his usual lunch hour was long gone when they decided it was time to go and rescue Dean and Castiel from each other.
“I’ll keep an eye on your file,” Gabe promised. “And grill your brother for all the dirty details! I can’t wait to see this train wreck happen.”
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Sam looked up from the newspaper when Dean blew into the apartment like a tornado.
“You’re not going to fucking believe it, but he took me to eat at the building cafeteria. Because he gets free lunch there. I still had to pay for mine of course and they just had this weird crap like hummus and these rice pellet things like you’re feeding freaking llamas.” Dean forcefully tossed his jacket over the back of the sofa, “I’ve never met someone so gifted at killing a conversation. He stared at me resentfully the whole time and didn’t laugh at any of my jokes!”
“Nobody laughs at your jokes.”
“Shut up, I’m hilarious. He’s just more sheltered than a monk and a pain in my ass. Not the good kind either.”
“So, your last match went out with a whimper I guess.”
Dean sighed, “Actually I’m taking him out Tuesday. Show that stuffy bird brain what a date is supposed to be like. Where did you disappear off to?” Sam told his brother about his lunch with Gabriel and Dean waggled his eyebrows suggestively. “Archangel, eh? Aiming high as always, Sammy.”
Sam rolled his eyes and went back to solving the crossword puzzle. This was going to be a treat.
-------------------------------------
Over the next few weeks, Dean took Castiel out on increasingly romantic and resentful dates. Sam rolled his eyes every time his brother insisted that it was just to “educate the asshole.” Sam may have made a snide comment about when Dean was going to move on to Sex Ed and he was met with utter disgust.
“I mean you’ve been on like five dates already, haven’t you at least made out or something?” Sam only asked because he’d never known Dean to go out with anyone he didn’t bang within the first week, not even in high school. He was concerned lest his only sibling had caught some kind of rare disease. Like monogamy.
“Ugh, gross. I wouldn’t kiss him if you put a gun to my head,” Dean said as he packed up a picnic basket for his lunch date.
“Really?” Sam raised an eyebrow and leaned a hip against the kitchen door jamb. “Because I’ve never seen you go to these lengths for a date before. I mean, man, you’re wearing a vest!” Dean forcefully tossed the bag of assorted gourmet cheeses in the basket.
“Oh yeah?” he challenged. “I’m a vest guy now. Ask anyone!” Sam stared at him skeptically.
“Dude, you always said they made you look like a monkey.”
“They make me look debonair! All the chicks dig it.” And Castiel, Sam would bet. Dean slapped the basket lid shut and grabbed the bouquet sitting on the counter. He gestured with it angrily at Sam. “I don’t need any lip from you, what I wear is my own damn business. At least I don’t have long hippy hair and a…stupid nose!”
Sam didn’t even bother to hold back his smirk. Weak comebacks were always a sure sign of Dean getting defensive. Dean stormed off to meet Castiel at the botanical gardens. Out of respect, Sam waited until he slammed the door before he texted Gabriel all the details.
Ever since their lunch together, they met up regularly under the pretense of Gabriel updating Sam on the status of his letter, (it was always, “sorry Sammy, not a peep,”) but really it was to gossip about their brothers and just chat. Gabriel had contacted him first, with a jokingly fearful phone call about Castiel’s “angry falcon glare” following his date with Dean. When Sam demanded to know how he’d gotten his cell phone number, Gabe had appeared on his desk with a quiet pop, pointed to himself, and exclaimed, “Hellooo? Archangel!”
Gabriel had the wildest anecdotes and Sam figured at least some of them had to be true. It got to the point where Sam memorized Gabriel’s elaborate and oddly specific coffee order. He half suspected Gabriel just got it to mess with the baristas.
They met up at their usual coffee shop later that evening. Minutes later, Gabriel was wiping tears from his eyes.
“I can’t believe that mook! He’s gonna wind up proposing to Castiel just to prove a point and my brother’s dumb enough to accept.”
“What do they even do on their dates? I mean I can’t imagine Dean or Castiel being lovey-dovey.”
“I asked ol’ Cas-pants, but he’s tighter than a clam about these things. We should find out, we should tail them on their next date.”
“I don’t know,” Sam hedged, he wasn’t entirely comfortable spying on his brother, but sneaking around with Gabriel sounded fun. Sam hadn’t had fun in a long time.
“Look, you know I hate to brag, but I am an archangel.”
“You’re an archangel?” Sam interrupted with insincere incredulousness. Gabriel swatted at him.
“Like I was saying, I’m all powerful, I can totally hide us so those love-hate birds would never notice.” Gabriel waggled an eyebrow. “What d’ya say, Sam?”
Sam was ashamed of how little convincing he needed and started to form a plan with the devious archangel.
-------------------------------------
Gabriel didn’t understand why he even needed a desk. An office, sure. All important people needed offices. But a desk? He just wasn’t a desk kind of guy. A desk only served to remind him of all his damn responsibilities. Instead, he preferred to think of it as a flat, ineffectual storage space. Whose bright idea was it to make him head of the Cherubim, anyway? Michael got the Seraphim (of course), Luci got the Malakim (that sort of made sense), Raphi got the Watchers (Dad help ‘em), and he got stuck with the love brigade.
Gabriel didn’t even like the whole matching system. It worked for some people, sure, and that was great. Heck, he’d even gotten a good match out of it once with Kali, but that sort of went down in flames (pun intended). What killed him was the rules. They were so stringent, arbitrary, antiquated. Everything he wasn’t. Worst of all, it left people like Sam Winchester all mopey and heartsick. The system must be flawed if someone like Sam was left out.
All the same, it was Gabe’s job to make sure things kept running. He sifted absentmindedly through his inbox, tossing meaningless memos aside -- didn’t angels know how to use email? -- until he came to something that made him pause. It was a large brown envelope addressed to him with the This Is Sort of Important seal stamped on the front. For one panicked moment, he thought it might be a match for him, but all matches were hand-delivered to ensure receipt. Besides, archangel matches required archangel approval, so one of his idiot brothers would have undoubtedly already dropped by to poke fun at him. Maybe that’s what it was -- they’d finally found someone for Raphael and needed Gabe’s approval. That guy could definitely use a good lay. He tore open the folder and scanned the familiar words quickly before his heart stuttered to a halt at the first name.
Samuel Winchester.
He didn’t know why he was so surprised. He’d put a flag on Sam’s file, after all. Just the same, a thick cloud of melancholy descended on his shoulders and his stomach sank knowingly. Of course the first guy he’d been interested in (like, actually interested in, not just a quick fuck, though he’d definitely be open to that, too) for decades would get a damn match. Just his luck. Out of pure curiosity, he scanned the rest of the letter until he came to the name of Sam’s supposed true love.
This time, his stomach didn’t sink -- it attempted to bust through his chest, Alien-style. The letter slipped from his fingers and he immediately dropped to the floor, scrambling to find it. They’d definitely have his ass if he lost a match like this one. It was a mistake, it had to be. There was just no way. He couldn’t subject Sam to... that. But even as he re-read the names, he knew it was no mistake. There were no mistakes. That’s what everyone said, anyway. And, in some weird fuck-off way, it made sense.
Gabriel groaned and slammed his head down onto one of the many piles of paper and candy wrappers decorating his desk. Just his fucking luck. Best of all, joy of joys, he somehow had to give the news to Sam.
-------------------------------------
At eight o’clock sharp, exactly the time they’d discussed, there was an enthusiastic knock at Sam’s front door. Gabriel was knocking out an off-beat rhythm when Sam finally opened it. He could only stare in shock for a few moments.
“You look, uh, interesting,” he muttered.
“I think the word you’re looking for is,” Gabe clicked his tongue and winked garishly, “18 karat.” The archangel -- archangel, that was still really hard to believe -- was dressed in crisp, straight-leg jeans rolled up the ankle to reveal bright white socks and shiny black loafers. He was also wearing a yellow checkered button-up and a bright red jacket that clashed horrifically with the whole outfit. Sam was almost certain there was decades-old pommade combed into his hair.
“That’s two words,” Sam finally pointed out.
“Whatever.” Gabriel shrugged. “I just figured I’d go with the whole drive-in movie theme. Admit it, you love it.”
“Yeah, sure, I love it. I’m this close to throwing on my poodle skirt and doing the Lindy Hop.”
“Lindy Hop was the 30s Sam, get with the picture. The 50s were all about the Jitterbug.” Gabe started flapping his arms in something that somewhat resembled dancing. “Now where’s the poodle skirt? I’m serious here.”
“I am not doing this in a poodle skirt.”
“Well, if you’d prefer to do it out of the poodle skirt, that’s fine too. Just keep the frilly socks, I’m begging you. Such a turn-on.”
Sam found himself grinning stupidly. It was really ridiculous how comfortable he was around Gabriel, even when the topic of conversation was crossdressing and innuendo.
“Fine,” Sam chuckled. “I’ll make sure the socks stay on.”
“But seriously, you can’t go dressed like that.”
“What wrong with how I dress?” Sam demanded, holding out his arms and looking down at his outfit. Just a plain button-up and jeans. Standard.
“As much as I love how shapeless your ass looks in those jeans, if you’re gonna be seen out with me, it’ll be in something more exciting than that.” Gabriel chewed on his bottom lip and looked Sam up and down. “May I?”
“May you what?” Sam asked, raising his brows. Gabriel gave him a ‘surely you jest’ sort of look and tilted his head to the side. Sam sighed heavily and let his arms drop to his sides. “Fine,” he grumbled. Gabriel grinned like it was Christmas morning.
“So glad you said that, Sammy,” he laughed, snapping his fingers. Suddenly, Sam had the strange and unfamiliar of fabric snug around his waist and air around his thighs. He was also holding what appeared to be a pot roast.
“Gabriel,” Sam growled warningly. He wobbled a little in short kitten heels as he attempted to take a step towards the archangel. The floral pastel skirt, frilly apron, and pearls made it slightly less menacing. Gabe laughed uproariously and snapped up a pipe that he clenched in his teeth and blew small, iridescent bubbles out of.
“Careful honey, you’ll burn the roast with that attitude,” he chuckled.
“Change it.”
“All right, all right,” Gabriel groaned, “have it your way.” He snapped again and Sam was thankful to feel denim wrapped around his legs again. He glanced down and noted a plain white shirt, black leather jacket, and short black boots.
“Acceptable,” Sam said with a nod.
“Glad it meets your standards, Princess,” Gabriel replied, giving Sam a sidelong glance that he hoped was subtle. Sam caught him at it and gave him the standard bitch face.
“Now can we go? Please?” Sam drawled.
“Sure thing, kiddo.” Gabriel leaned up and placed two fingers to Sam’s forehead, then came the strange, gut-twisting sensation that came from being angel mojo-ed 30 miles across the county.
-------------------------------------
“So let me get this straight -- you magic’d a car here for us to sit in, but you couldn’t drive it?” Sam drawled, eyeing Gabriel, who was way too into his weird greaser outfit. When Gabe had first showed him to their spying vehicle (he kept calling it ‘Barracuda One’), it was a cherry red Hummer. One look from Sam had made him snap it into a more manageable vintage convertible.
“Why would I drive?” Gabriel replied. “Who even drives any more?”
“Humans drive,” Sam pointed out. Gabriel shrugged and slipped into the driver’s seat.
Dean and Castiel were nowhere to be seen, but Gabriel insisted that they were close by. Sam wondered if he had a tracking device for Castiel or if it was just natural talent. Sam leaned against the side of the car and examined the white leather interior -- a detail Dean would have appreciated -- and a bored teenager passed by with snacks.
“Ooo, popcorn! Sam, get me popcorn.”
“Can’t you just mojo yourself some popcorn?”
“It’s not the same as you bringing me popcorn, Sam,” Gabe insisted, turning puppy-dog eyes on him, complete with a slight lower lip quiver.
“Fine,” Sam sighed.
“Oh, and Jujubes! And Junior Mints! And Sour Patch Kids!”
Gabriel was still calling out his candy demands when Sam turned and started trudging towards the snack stand. He ended up with a large popcorn, sodas, and a sampler pack of movie candies the cashier had recommended when he tried to buy one of everything. He shoved his way back through the crowd, loaded down with way too much sugar, then stopped cold when he came to a sudden realization.
This was a date.
Not lunch, not coffee, not admittedly flirtatious text message gossip. A real, live date. Their second one, actually, if he counted the day they’d met. They might be there to spy on their brothers, sure, but that didn’t change the fact that they were dressed up, in a car, alone together, at a drive-in movie, and Sam had just bought Twizzlers separately because they didn’t come in the sampler pack and he thought Gabriel would like them.
A trickle of cold, nervous sweat ran down the back of his neck. It wasn’t that he’d never dated -- just because he was a romantic about the letter thing didn’t mean he was a monk. He’d dated girls, a couple of them serious, and one guy during college, but he’d stayed away from dating recently in the hope that he’d finally get a match. He just wanted to avoid potential awkwardness.
But despite his best intentions, he’d ended up on a date, a real date, with Gabriel. And he was having fun, and there was this weird sensation that might have been feelings, and shit.
He blew out a breath. He just had to keep his cool. It was nothing, an infatuation. It was fun and easy, nothing that would keep him from getting a letter, nothing that would cause a dramatic scene if it ended. Gabe knew what Sam wanted, after all, and despite his insistence that he couldn’t make the system work any faster, Sam was more confident in his chances with the head of the Cherubim in his corner. Sam felt certain that despite his flirtatiousness, Gabriel had his best interests at heart. His shoulders relaxed and he continued walking towards the convertible. When he appeared with snacks, Gabe made a terribly inappropriate sound.
“Marry me,” he gushed, which made Sam’s face go uncomfortably warm. “Just in time -- our unlikely lovebirds have finally made their appearance. I think they’re arguing about AC/DC. Hard to tell.”
“Here,” Sam mumbled, shoving the Twizzlers and other assorted candy into the angel’s hands. He could feel another bead of sweat trickle down his face. Probably the heat. Definitely the heat.
“Twizzlers!” he exclaimed. “How did you know? Despite popular belief, bribery will get you everywhere.”
“I thought you might appreciate sticks of pure corn syrup.” Sam chuckled nervously, scanning the crowd for Dean and Castiel.
“What’s up with you, Sam?” Gabriel asked, raising a brow. “You’re sweatin’ like a sinner in church. Is it the socks? It’s the socks. I knew it.”
“Yeah Gabe, it’s the socks.” Sam rolled his eyes and slid into the car beside the other man. Gabriel elbowed him in the side, his usual smirk a little bit softer, a little bit warmer than usual, but didn’t press the matter.
“You ready for this reconnaissance mission, Sierra Whiskey?”
“Please don’t call me that.”
“Whatever you say, Sugar William.”
“Just don’t.”
“Desert Fox. Jungle Tiger. Golden Moose.”
“Gabriel.”
“Call me Eagle Panther. Three o’clock!” Gabriel shouted suddenly and shoved down Sam’s head. Which was ridiculous as it just bent him over awkwardly and hid nothing. If anything, it looked like he was doing a ‘favor’ for Gabriel.
“What the hell, man!” Sam sputtered and after a minute, Gabriel let up on Sam’s head and he straightened up. He fixed the archangel with a glare, but Gabriel didn’t seem very contrite.
“Sorry, Laverne and Shirley drifted a little too close to our hideout. They parked a few spots up.” Sam frowned.
“Couldn’t you have just made us invisible? Did you really have to try to put my head in your lap?”
Gabriel slowly looked over at the human and just stared at him and then, like an owl, moved his head back to face forward. It was actually a pretty good Castiel impression, whether intentional or not. Sam decided to let Gabriel’s weirdness slide, he was having a good time otherwise.
He craned his neck to see two figures in Dean’s beloved Impala. They sat at practically opposite ends of the car and didn’t appear to be interacting at all. Disappointing, but not unexpected.
“When will those idiots get a clue,” Sam muttered. Gabriel hummed in agreement.
“It’ll be great to watch it implode. Either they’re going to kill each other or start humping in public like dogs in heat. Considering I don’t think my baby bro is even aware he has a dick, I’ll go with the former.”
Sam didn’t respond, he just watched the pair. Gabriel shifted restlessly next to him like a child who needed to be entertained every waking second or he got antsy. Usually, that kind of impatience would irritate Sam, but it was oddly endearing to think angels were supposed to be these ancient, serene creatures and Gabriel was more like a hyperactive five year-old.
“I think it’s going well, considering,” Sam commented after Dean shifted fractionally closer to Castiel. “They might get there sometime this decade.”
“You really think they’re gonna work out, don’t you?” Gabriel asked incredulously.
“Dean is practically pulling Castiel’s pigtails and I’ve never seen him do this kinda thing for someone even if he claims it’s motivated by spite.” Sam knew his brother better than anyone.
“Whatever. They’re going to crash and burn, the system’s all jacked up anyway. Your brother isn’t the first to get ten letters.” Sam shook his head.
“I’ve seen Dean manipulate it for all it’s worth, but I think it’s finally beaten him in the end.”
“You’re funny, Sam. Why do you want this to work out so bad?” Sam ducked his head and stuffed some popcorn in his mouth. “Oh my God, you think it’s romantic, don’t you? Sam, there is nothing romantic about an arranged match. Love shouldn’t be forced on people, humans are supposed to thrive on free will.”
“You can say what you want, but I’ve seen it work,” Sam began, a bit defensively, “my parents were each others’ first match and I’ve never seen two people crazier for each other, even after years of being together. It might be idealistic of me to hope for something as wonderful as that, but I still want it so bad.” Sam felt embarrassed at how much he revealed, he was usually very private about these things. Something about Gabriel lowered his guard though. The archangel eyed him oddly, and something that looked suspiciously like guilt flared there, but was gone in an instant.
“You haven’t been saving yourself for Mr. Right, have you? Because that would be a damn shame.”
“I’ve dated on my own. My head isn’t that far in the clouds. But, I always felt like, I don’t know, something greater was waiting for me. Like I’d get a letter, meet my match, and everything would just click into place.”
Sam stopped as he realized he was waxing poetic. Dean would have been mocking him a long time ago and he would have expected the same of Gabriel, but he had just observed Sam in contemplation. He seemed disillusioned with the letters. Understandable after looking at it an inch from your nose for centuries, but there was a flame of hope in Sam that couldn’t be doused. Its glow had loomed in the background of every serious relationship Sam had.
He remembered when Jess left him, saying even if everything was perfect Sam wouldn’t have the letter to prove it. He did feel a little regret about that. If he hadn’t sealed his heart like an envelope, Sam suspected Jess would have been so easy to love completely. Gabriel sighed and brought Sam back to the present.
“You’re one hell of a guy. Shine on you crazy diamond and all that. Whoever snags you is one lucky bastard.” For some reason, his voice sounded somewhat sad.
They both sat in silence, half watching the movie. After a few minutes, Sam spoke up.
“Thanks for not laughing at me.” Gabriel scrunched his nose.
“I’ll laugh when you say something funny, Jerry Seinfeld. Now, quit hogging the Twizzlers.”
Gabriel gnawed at the red candy and snuck a glance over at Sam. The big lug was splitting his attention between the movie screen and his brother’s car, probably planning out Dean and Castiel’s damn wedding or something. Gabriel subconsciously touched his jacket over where the inside pocket was.
The letter wasn’t so much as burning a hole in Gabe’s pocket as smolder annoyingly. It wasn’t that he meant to keep it from Sam, he’d just gotten distracted. After all, Sam had brought him enough Twizzlers and gummy bears to dispose of a weaker man. He had an obligation to finish it all. Then there was Castiel and Dean, being ridiculously entertaining. Finally, there was Sam -- Sam, who just kept being so damn thoughtful and cute and clever and sexy as hell just for extra torture.
And... and he just didn’t want to give him the letter, okay? Why ruin a perfect night? Sam and his freaking smarmy-ass prince charming had waited long enough, hadn’t they? Whatever. He just wasn’t great at giving away things he liked. And Sam had -- somehow -- become a thing that he liked, damn it. He’d do it tomorrow. Or the next day. or maybe he’d just give it a week. In case of... something. Gabriel moved his hand to steal a fistful of popcorn from the bucket on Sam’s lap.
Continue to Part Two
Author: menofsweaters and moosetaches
Artist: saffron_zephyr
Pairing: Sam/Gabriel, Dean/Castiel, unrequited Sam/Lucifer, Lucifer/Michael if you squint
Rating: PG-13 for language and some sexual references
Warnings: None, unless any of the above pairings squick you out. It’s pretty tame.
Word Count: 19,377
Summary: Sam has been waiting for the Cherubim to match him up with his true love his entire life, but so far, he's had no luck. While Dean fully intends to stay a free-wheeling bachelor forever, Sam is desperate to find a match before his time runs out. When his brother is paired with an unlikely angel named Castiel, Sam is thrown head-first into a world of archangels, love letters, and an alarming amount of vests. However, as he gets closer to a particularly charming archangel named Gabriel, he starts to doubt the system. Hijinks include Gabriel in sock hop garb, spying on Dean and Cas, way too chipper Samandriel, creeper!Michael, and Gabriel and Lucifer fighting over Sam's pretty face (sort of).
Link to full fic: AO3
Link to art masterpost: LJ
Sam was scowling as he watched Dean stick a thumb tack viciously through the red envelope, pinning it to the wall with all of the others. Dean smirked at it like it was a trophy he’d stolen from a twelve-year-old.
“What d’ya think, Sammy?” Dean asked jovially, turning to grin at his brother.
“I think it’s sick,” Sammy replied. “You are sick. There is something wrong with you.”
“Hey, if there’s something wrong with me, then there’s something wrong with you.” Dean brushed past him, still grinning, on his way into the kitchen. Sam rolled his eyes.
“I just don’t understand why you do this. Normal people don’t do this.”
“Hey, any red-blooded guy would be proud to show that he’s not tied down to some chick,” Dean insisted, pulling the refrigerator door open and peering at its contents. “I’m just glad it’s almost over,” he continued, grabbing the ingredients for what would most likely be a massive abomination of a sandwich.
“You know, you can opt out of the pool,” Sam pointed out.
“Where’s the fun in that?” He gestured to the nine red envelopes pinned and taped to the wall of their apartment, all in various states of disrepair. “I came, I saw, I conquered, dude. Even angels can’t keep me down. The whole destiny thing is bullshit, anyway.” Dean pulled several slices of bread out and laid them on the counter. He almost offered Sam a sandwich, too, but his brother was giving him that weird, angry constipated face again, so he decided against it. Sam could make his own damn lunch.
“That bullshit is how Mom and Dad got together, Dean.” Sam sighed heavily and practically collapsed into one of the chairs in their small dining room, restlessly straightening his tie. “I get that you don’t want that for yourself, I just don’t -- “ He snapped his mouth shut and looked away.
Sam could see the guilt immediately apparent on Dean’s face. Sam knew his brother hadn’t meant to flaunt what he had right in front of him. Dean knew, everyone knew, for goodness’ sake, that Sam was into it -- the whole idea of fate, of winged cherubs choosing some perfect soulmate for everyone. Dean just didn’t buy it. Hell, Dean could probably be single forever and stay at least somewhat happy as long as he got laid now and then. Ever since Dean had gotten that first letter, that first name -- and damn if that hadn’t ended spectacularly -- it had become a kind of game. A way to outsmart the system. The cupid brigade insisted that they could find the perfect match for anyone, and Sam knew his brother was determined to prove them wrong. Once Dean got that tenth letter, the tenth match, and that one failed like all the others... Well, then the angels would have to admit that they were wrong, and put it on some official documentation to prove it, too. Once that happened, he’d win the game.
Sam didn’t see it as some stupid game, though, and he could tell that Dean sort of pitied him for it. Whereas Dean waited for the next letter so that he could continue his mission of sexual conquest, Sam waited for the naive idea that a piece of paper from a bunch of douchebags with wings would help him find his True Love. And he’d been waiting for twelve years. If they kept him waiting, if Sam’s thirtieth birthday rolled around and he still hadn’t gotten a letter, that was it. They took him out of the pool. Labelled him as “unmatchable.” It was sad, it was terrifying, and, according to Dean, really, really stupid.
“Hey, listen,” Dean grumbled. “I didn’t mean to, ya know, make you feel bad or anything. I mean, the whole system’s fucked. You shouldn’t let it bother you.”
“Easy for you to say.” Sam was pouting at the kitchen table, sifting through the bills and junk mail left there.
“Look, you’re a good-looking guy -- I mean, you gotta be, you’re related to me -- “ Dean gave his brother a smug look. “You’ve got a job and a car and you’re not a complete moron. Just go find a date on your own.” Sam mumbled something incoherent and Dean shrugged in defeat. It was the same argument they always had. Sam was depressed the cupids hadn’t stuck him with one of their little arrows, Dean told him to find a girlfriend on his own, Sam stubbornly refused. He knew why. Dean glanced up at one of the photographs of their parents on the wall. It was taken when they were younger, and they were kissing with silly smiles on their faces. Mary was wearing a blue dress.
Yeah, Dean got why Sam acted this way. He just didn’t know what to do about it any more.
“Come on,” he grumbled. “We’d better get going. I know those seraphim tightwads like to keep you on a short leash.” Sam opened his mouth to say something scathing, but seemed to think better of it.
“Jerk,” he muttered, grabbing his briefcase as Dean attempted to shove the giant sandwich he’d spawned into a paper bag.
“Bitch.”
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The Winchester brothers had a system. Dean worked with the Watcher Division, looking out for the safety of the citizens. It was a joint venture between the angels there and humans, dedicated to protecting the populace from criminals and monsters. It was perfect for Dean, and the main office was just blocks away from the Seraphim, which was convenient for his brother.
Sam had worked for the Seraphim ever since he got out of school. They were the foremost governing body of their world, taking charge of creating the laws as well as upholding them. He guessed you could call it a dream. He was still working to help people, but more on the legal side of things. He preferred it that way. Dean pulled up in front of the Authority complex, buildings grey and ominous, and Sam jumped out, the same as every morning.
“Take care, Sammy,” Dean said with a little wave, pulling back out into traffic towards the Watcher building. Sam shoved his hands in his pockets and strolled towards his office.
He passed the smallest of the three buildings along the street, home of the Malakim envoy, all smooth concrete reaching up into the sky, adorned only with the winged crest of the Malakim. Then there was the Cherubim building, with its glittering glass dome and elegant columns. Three statues stood out front: an eagle, an ox, and a man. It was a somewhat foreboding building for such a romantic purpose. Sam felt like it was mocking him. Finally, he came to his building. It looked much like a gigantic courthouse, with an open green lawn stretching out in front. It was slightly cold, but it was familiar. Sam couldn’t help but smile to himself.
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Sam liked his job, but he was glad he had the weekend ahead of him. He loosened his tie and sat heavily in his armchair. The leather creaked as he shifted in place and Sam searched for the TV remote on the messy table next to him. How Dean managed to create so much clutter was a mystery that had haunted Sam for nearly three decades. He was just about to give up his hunt when the doorbell rang.
He swung the door open to reveal a kid who couldn’t have been more than sixteen wearing a red striped uniform and a big smile.
“Greetings on this beautiful day, sir,” he chirped, completely oblivious to the overcast skies behind him. “I’m with the Cherubim, my name is Samandriel.” Sam brightened at the introduction.
“Hey! My name is Sam, too.” Samandriel was positively delighted out of his pants by the news.
“Isn’t that swell? The world is full of happy coincidences.” Sam sometimes wondered if the Cherubim were on some kind of stimulant. Coffee, soda, cocaine, maybe meth.
“How can I help you, Samandriel?”
“Gosh you’re so kind, I have a letter here for someone very special,” Samandriel teased in a sing-song voice and pulled out a red envelope from his messenger bag. “Is there a Dean Winchester residing at this address?”
Sam’s face fell. Of course, what else had he fucking expected? He snatched the envelope from the cherub’s hand and slammed the door in his face just as Samandriel reminded him to have a delightful day.
Dean thought it was funnier than hell when he got home a few hours later.
“Damn, you kidding me? I just got one of these a week ago. They must want me out of the pool fast. Can’t believe you gave that kid a hard time.”
Sam frowned and muttered, “He’ll be fine, you know how they are. He probably thought a strong wind came through the apartment and shut the door accidentally.”
Dean hummed in agreement and tore open the envelope with no finesse and read the letter inside as he fished a few Cheetos out of the bag on the coffee table. He laughed obnoxiously and Sam kind of wanted to strangle him.
“It’s another angel, guess I haven’t defiled enough of them. Well, not that she was--” Dean cleared his throat. “Chick’s name is Castiel. Get this: she works in the accounting department for the Cherubim. I didn’t even know they needed accountants. I bet she’s a sexy librarian type, all brainy with glasses. Might as well go out on a good note.”
“Are you sure Castiel is a woman? She has one of those angel gender neutral names.” Sam only asked because it was a common mistake to make. Dean shrugged.
“Okay, so maybe he’s a sexy librarian in a sweater vest. Either way, totally my type.”
Sam rolled his eyes. Everybody was Dean’s type. He rubbed his forehead in exasperation.
“I just can’t believe this, you just broke up with that Carmen or whatever.” Dean shrugged.
“Them’s the breaks, kid.”
Sam couldn’t handle his brother and stormed off to his room like he was a teenager again.
“Oh, come on, Sammy. Don’t be sore!” He followed after Sam, waving his letter around. “There’s all this extra crap written here, I need you to sort through the legalese for me.”
“Figure it out for yourself, I’ve got a headache.”
“Sammy, Saaaammy. Please?”
Sam turned on his heels and took the letter from Dean to shut him up. He scanned the paper and frowned.
“It basically says you need to meet this Castiel at the Cherubim headquarters before any ‘informal meetings,’ I guess they mean dates.” He pointedly ignored Dean’s smug noises. “It’s a very old fashioned thing. I’ve never actually heard of anyone doing it in this century.”
“Great, old fashioned. Prude more like.”
“Well, I guess it means you’ve got to go to the Cherubim office tomorrow.” Dean made a face like he’d eaten something unpleasant.
“Ugh, I don’t want to go there. Sounds stuffy. Hey I know! Why don’t you tag along, Sam? I know you’ve always had a hankering to go in there. Who knows, maybe you can bribe one of the cupid guys to hook you up with a swimsuit model or something.”
“I don’t think it works that way, Dean.”
“Lighten up, Sam. Come on, come with me. It’ll be fun.” Sam worried his bottom lip.
“You just said you didn’t want to go, why is it fun all of a sudden?”
“I don’t know, brotherly bonding or some crap. Just go with me, I promise I’ll get you some of that spinach salad you like at the Roadhouse later. Hey you like that.”
“Fine,” Sam shook his head, “it just better not take too long.”
“Never takes too long with me, Sammy, if you know what I mean.” Dean cocked an eyebrow and smirked. Sam sighed heavily. His brother was difficult to deal with sometimes, but he was genuinely curious about the inner workings of the Cherubim Headquarters. Maybe he could find somebody and ask about his fate and if he’d be getting a letter anytime soon. Perhaps there was a clerical error. That would explain everything.
-------------------------------------
“Well, it’s clean,” Dean said. It was a vast understatement; the inside of Cherubim Headquarters was blindingly white with hyper-polished marble floors and columns which supported the nose-bleed high ceiling. A tiny metal plaque proclaimed it to be called the Solomon Building. It smelled antiseptic and Sam was pretty sure it would be safe to perform surgery in here.
“The angels at my precinct are total slobs. So, are we like the only ones here?” Dean’s voice echoed through the foyer, “Hello?”
Sam had always been, well, not awestruck exactly, but definitely intrigued by the angels. It was probably a big part of the reason he’d always wanted to work with the Seraphim. He was also, predictably, puzzled by them. Angels as a whole seemed to have a somewhat unsteady grasp on How to Interact with Humans 101, but some were definitely better than others. While the Watchers at Dean’s precinct were boisterous, the angels at Sam’s office were cold; while the Malakim were always sharp and intense, the Cherubim were undoubtedly chipper. One thing they all shared was a certain drive and a decidedly inhuman air.
He thought of Samandriel and winced inwardly at his earlier behavior. He was having a hard time imagining such a sweet kid in such a cold facility when a familiar voice rang out.
“Sam?” Samandriel had just freaking appeared, like angels were prone to do, and was grinning from ear to ear. “Well fancy seeing you again! It’s me -- Samandriel!”
“Yeah, I, uh, remember you,” Sam mumbled. Samandriel looked like he might faint from joy.
“Well, I’m here for a Dean Winchester,” he chirped, holding up a piece of paper. “That’s not you, is it?”
“No, that’s my brother. I’m Sam, remember? You literally just called me by my name.” Samandriel just shrugged.
“You never know! I don’t like to make assumptions. It could be your middle name, or a nickname!”
“Why would my nickname be my brother’s name?”
“Nicknames are funny that way. Sometimes folks call me Alfie and I have no idea why!” Sam stared, perplexed, then pointed to a spot behind the angel.
“He’s over there.”
Samandriel proceeded to lead Dean up a large staircase, jabbering about how exciting it all was, with no apparent need or desire to breathe. Dean’s face was flashing between irritation, confusion, and something that might have been fear.
Sam sighed and resigned himself to waiting. Peering around at the polished marble, he couldn’t help wondering where the letters came in and went out. He peeked around the corner. If he could just see his file, maybe it would all make sense...
“You lost?”
Sam whipped around and found himself staring down at a stranger wearing a green jacket and a self-confident smirk. He didn’t look particularly like an angel, but Sam guessed he must be one from the way he’d appeared out of thin air. He had an open, mischievous sort of grin, and Sam found himself unable to explain his mediocre snooping.
“I, uh,” he stammered.
“I’m sure you’re used to clearing tall buildings in a single leap, but this place can be a maze. Want a tour?” the angel asked, unfazed. Sam blinked. He couldn’t think of why not.
“Sure, I guess,” he blurted out, sounding a little more eager than he’d intended. “That is, if you’ve got the time.”
“For you, kiddo? I’ve got all the time in the world. Gabe.” He held out his hand and Sam grasped it automatically. He wondered if there was a good way to ask about his file, a way to bring up his complete and utter lack of romantic potential, without sounding too desperate. Maybe he didn’t care if he sounded desperate -- he was desperate. This angel dude could be the answer to his problem.
“I’ve been known to render people speechless now and then,” a warm voice cut through his inner monologue, “but usually this is the part where you tell me your name.” Sam flushed and jerked his hand out of the guy’s -- Gabe’s -- grip.
“Sorry,” he muttered. “Just out of it, I guess. Sam. Sam Winchester. I work over with the Seraphim.” Gabe’s eyebrows jumped up.
“Cripes, you’re with legal? This isn’t an inspection, is it?” he teased. “Here to shut us down for good? I know how you lawyer types hate fun and love and basically everything beautiful in the world.” Sam couldn’t help but laugh.
“No, just visiting.”
“Promise?”
“Promise.”
“I guess I can trust you then. You’ve got one of those faces. Come on, Sammy, let me show you the wonderful world of the Cherubim! I can arrange for some Oompa-Lumpas if you’d like.”
“Uh, no, that’s really okay.”
“Your loss.”
Gabe proceeded to drag him around the foyer, pointing out ancient sculptures and paintings and proclaiming most of the artists to be either douchebags or passably attractive. He didn’t mention anything about letters or files, though. Sam found himself wondering exactly what he’d gotten himself into when they began scaling the staircase he’d seen Dean go up. He surreptitiously glanced around, looking for something that might have been a file room while Gabe blathered on beside him.
“--And that’s where I drank Camael under the table. I guess that whole flaming sword thing was to save face. What a lightweight. And over there’s where I made it with Himeros. I wouldn’t recommend it, he’s all tongue. Are you even listening? This is some important history here, buddy.”
“Oh, um, yeah! Sorry.” Gabe narrowed his eyes.
“No one seriously comes to cupid HQ for a tour of the facilities. Or listens to me for that long. What are you really here for?”
“Well, I came here with my brother. Some kind of meeting.”
“Yeah? And what else?”
Sam felt his face go hot. Suddenly his missing letter problem seemed frivolous, juvenile. Definitely not something he wanted to talk about with a stranger -- even a chatty, easygoing stranger with a nice ass. Scratch that last part. He’d sworn off dating for the time being. But Gabe was staring at him with an earnest, piercing gaze, head slightly tilted, waiting for an answer.
“Well,” Sam heard himself say, “there is -- ”
“Sam!” Samandriel’s now-familiar voice cut through the conversation. The angel beckoned them forward. “And Gabriel! It’s such an honor to see you again, sir.” He looked a little tongue-tied and Sam wondered exactly what Gabe did, or Gabriel, apparently... it must be a popular angel name, like Jessica. Or David. Whatever.
“Come on, it’s time for the formal meeting. This will be so wonderful!” Samandriel got a far-off, starry-eyed look that Sam pointedly ignored.
“Wait a second,” Gabe began, looking at Sam sideways. “You said Winchester, right? Are you the one that’s unlucky enough to be matched with my brother? Say it ain’t so.”
“Uh, no, it ain’t so,” Sam mumbled. “That’s my brother, Dean. So you’re... Castiel’s brother? I mean, I guess all angels are brothers, aren’t they?” Gabe shrugged.
“Sort of? It’s complicated. More of a brotherly bond, not so much by blood, though I do have some of those.”
“Huh?”
“Brothers. Like real brothers. Three of ‘em. Pain in my ass.”
“And this Castiel is one of them?” Sam made a mental note that he had been totally right, Castiel was a dude. Not that Dean would mind, despite his macho attitude.
“Nah, Cassie’s just special.” Gabe shoved his hands in his pockets and chuckled. “Heh. My brother is gonna bone your brother.” He winced. “Well, more realistically, not bone. Actually, I feel kinda bad for your brother. What’s his name again?”
“Dean,” Sam grumbled. Dean, Dean, Dean. That’s all anyone ever wanted to talk about.
“My condolences to Dean.” Gabriel straightened up and slapped Sam on the back as Samandriel led them into a meeting room. “Time to play chaperone, Sammy.”
-------------------------------------
The room was pretty unremarkable, like any small office. Although hopefully most offices were devoid of Sam’s brother standing in the middle of them glaring at some equally sore guy in a trench coat. Sam couldn’t leave Dean alone for ten minutes before he managed to piss someone off. Samandriel was standing between the pair, beaming like there was no other place he’d rather be than the center of an angry alpha male sandwich.
“Sam, you’ve finally arrived and Gabriel, sir!” Samandriel vibrated with excitement. Sam tried to catch Dean’s attention, but he was too busy boring a hole into mystery trench coat guy’s face. Gabriel leaned over to whisper to the human.
“Your brother makes friends fast.”
“Yeah... Is that Castiel?” Gabriel rolled his eyes.
“I hope your brother doesn’t like having fun.”
Samandriel cleared his throat and spoke, “Now that we’ve gathered it’s time to proceed. This is my first time doing this, so sorry for any mistakes!”
“You got promoted, huh?” Sam asked, trying to relieve some of the lingering awkwardness he felt about the young angel. Samandriel glowed, but Castiel interjected with a voice blues singers would envy.
“He is the only one who wanted to do it. Everyone else was busy.”
“It’s an honor,” Samandriel squeaked pleasantly. “Now are you Dean Winchester? And you, Castiel, Angel of the Lord?”
“Yes,” they spoke simultaneously in matching harsh tones.
“And you, Samuel Winchester and Gabriel, brother to Castiel have witnessed the meeting of this pair matched by the divine grace of Heaven?”
Sam and Gabriel agreed. It felt weirdly like they were attending a shotgun wedding. Samandriel clapped his hands.
“Then it is done! It is strongly encourage that the matched pair go on an unchaperoned outing together,” Samandriel spoke in a stage whisper as though such a concept was scandalous in the 21st century. Dean huffed and finally tore his gaze from the rigid angel.
Castiel spoke woodenly, “I know a place we can go. I must fetch an item from my office, but I will promptly return to escort you.” Before Dean could agree, Castiel vanished on the spot.
“What happened between you two?” Sam asked, Dean crossed his arms and glared darkly.
“I don’t want to talk about it.”
“Castiel is in accounting, he’s not a people person.” Gabriel shrugged. Sam furrowed his brow.
“What do angels need an accounting department for?”
Gabriel just gave Sam an expression that read, ‘why do you think, Dumbo?’ Then Castiel reappeared next to Dean who nearly jumped out of his skin and cursed loudly. Castiel watched his display apathetically and when Dean’s rant was finished, he requested that the human follow him. Dean obviously wanted to do the exact opposite of whatever Castiel told him, but marched after him out of the office with a gruff goodbye to Sam.
Sam watched his brother leave and looked back to see Samandriel smiling dopily at him and Gabriel like he had been for the past five minutes. Sam spoke quietly so only Gabriel could hear him.
“Is he alright? He kind of comes off like he’s been lobotomized.”
“Well, he did used to work with Naomi, but he’s just, uh, chipper.” Gabriel then spoke at full volume, “Good job, Alfie. Go see if someone needs help… somewhere. I don’t know, just figure it out.”
Samandriel saluted and disappeared. Angels were fairly weird, Sam decided. Watching Castiel and Dean leave for their (probably super awkward) lunch date, Sam felt his shoulders slump downwards in a mix of jealousy and resignation.
“So how do I get out of here?” he grumbled.
“Leaving so soon? We were in the middle of an important conversation about my sexual conquests and your super secret desire to be a cherub or something.” Gabe snapped his fingers and coffee appeared in Sam’s hand, warm and tempting through the paper cup. Gabe sipped on his own magical angel coffee, which was topped with a generous mound of whipped cream.
“You were going to tell me something?” he prompted. Sam looked down and shuffled his feet, which was ridiculous, because he hadn’t shuffled his feet in embarrassment since high school. He was a grown man, dammit! He reminded himself that this was business -- Gabe worked here, and was some kind of big shot too, so it was his responsibility to help, right?
“Come on, spill,” Gabe urged. “Unhappy with your supermodel match? Looking for more of a sexy nurse type? Because that can be arranged.” He waggled his eyebrows, which definitely did not make Sam almost spit out his coffee.
“No, no, kind of the opposite, actually,” he admitted.
“Been a while between letters? I wouldn’t worry. Sometimes the celestial matchmaking service is a little slower than you’d like.”
“No, it’s that... well, I’m almost 30 and I-I’ve never gotten a letter.” Gabe actually looked shocked for a moment.
“Seriously? Never?” Sam shook his head, defeated.
“Wow. I mean... wow. The Almighty really dropped the ball on that one. That’s a bummer, Sam.”
“I was actually hoping to, I dunno, check out my file or something. Make sure there’s nothing... wrong. Out of the ordinary.”
“No one gets access to their own file, Sam,” Gabriel sighed. “Not even angels.”
“That makes sense.” Sam tried not to seem too disappointed, but Gabe’s sidelong glances were surprisingly observant.
“But I could check on your file, if you’d like. Make sure you’re not labelled as a serial killer. You’re not one, right?”
“No!” Sam laughed. “I’m not. I swear.”
“That’s just what a serial killer would say. But I’ve got a soft spot for lonely murderers. I’ll take a look.” He glanced at an elaborate clock on the wall that was probably older than Sam. Two Sams. Maybe three. “Who knows how long our idiot brothers will be. What say you wait right here, I’ll nab your file, and we can grab lunch?” Gabriel flashed a rather blindingly charming smile and Sam fought against the urge to roll his eyes. He wasn’t stupid. He knew what Gabe was up to, and it was a decent excuse for a date. He’d promised himself no dating until the big 3-0, but he couldn’t see the harm in a simple lunch.
“Yeah, okay,” he finally agreed. “Sounds great. I really appreciate it.”
“No sweat, kiddo,” Gabe replied brightly, rocking back on his heels. “Just stay put. I’ll make sure your file is spick ‘n span.”
“You, uh, must be a big shot around here if you can just poke around in people’s files,” he chuckled. “You’re Samandriel’s boss, right? Someone needs to stop giving that kid stimulants.”
“You could say that,” Gabriel hummed. Sam rose an eyebrow.
“What are you, the CFO?”
“We’re angels/i>
“You have accountants,” Sam pointed out.
“We have accounts.”
“So... what? You’re the president? The head honcho? The final boss?”
“I’m kind of everyone’s boss. Well, everyone here.”
“Are we talking everyone in this office or everyone on this floor or...?”
“More like everyone in this building. And a few others, I think.” Sam gaped.
“Wait, wait. Your name is Gabriel.”
“Don’t wear it out. Or do. But I’d prefer that under different circumstances, like screaming circumstances.”
“But not like... the Gabriel, right? It’s gotta be a popular angel name.”
“Um, Sam? There are no ‘popular’ angel games. We’re all one of a kind.”
“But... the Gabriel is an archangel!” Gabe spread his hands wide.
“You caught me. So, lunch? I’m thinking Thai.”
“I can’t go to lunch with you! You’re an archangel!”
“Ah, ah, ah,” Gabriel waggled his finger, “you already agreed. We have a verbal contract. No take-backsies. See you in a jiffy, Sam.” With that, he winked obnoxiously and disappeared, leaving Sam to mull over exactly what he’d gotten himself into.
After five minutes of having a nervous breakdown over the fact that he was going on a date (just lunch Winchester, pull yourself together) with an archangel (it’s just a title, meaningless really, and you’re taller anyway) which felt like an eternity, Gabe reappeared. Sam tried not to jump or clutch his pearls like a distressed southern belle.
“Miss me?” Gabe said with a smirk, holding up a file folder triumphantly. It wasn’t very impressive, really. Sam was vaguely disappointed. Just a thin file folder, white, with a slight silvery sheen. He could see there were papers inside -- chronicles of his life, maybe? His sexual history? His last physical? There was no way to tell, short of snatching it away from an archangel.
“No peeking, Sam,” Gabriel tutted, as though he could read Sam’s mind. Maybe he could. Without warning, Gabe reached up and pressed fingertips to Sam’s forehead, and suddenly he had the awful, exhilarating sensation of his brain being sucked out through his pants pockets and rearranged into a tasteful bouquet. Being angel-teleported was an experience he’d had a few times before, usually when his angelic coworkers were impatient with mundane travel arrangements, but he got the feeling that Gabriel had a little more... juice. It left his skin tingling and the usual nausea subsided almost instantly.
They were in a small restaurant packed with brightly colored tables and chairs and the the air was permeated with the smell of peanut sauce and hot chiles. The angel dragged him to a table in the corner. An unimpressed-looking waitress soon approached.
“The Archangel Gabriel,” she greeted monotonously. “As I live and breathe.” She wasted no time and placed some creamy iced beverage in front of him, then looked at Sam expectantly.
“Thai iced tea?” Gabe offered, shoving the glass in Sam’s face. Sam tentatively took a sip, then grimaced.
“Wow, that’s,” he choked a little, “really sweet. I’ll just have water, thanks.” Gabriel looked disappointed, then proceeded to order some kind of elaborate noodle dish that involved fish balls and made the waitress’ scowl deepen. Sam chose a salad.
Gabriel leaned back in his chair and flipped through Sam’s file, brow furrowed, as they waited for their food. His eyes flicked sharply across the paper and Sam fidgeted nervously. That file undoubtedly had some very intimate information in it, and watching Gabe read it was understandably nerve-wracking.
“I hate to break it to you, kiddo,” he began, “but there’s nothing wrong with your file. Everything’s in order. I honestly don’t know why you’ve never been matched.” He sounded apologetic, but there was no pity in his voice, which Sam was thankful for. “That’s heavenly Bachelorette for you. Take it from me, you don’t need the Almighty to hook you up with anyone.”
“That’s not--” Sam bit his tongue as their food arrived. He didn’t want to snap at Gabriel, or spill his guts about why he wanted that letter so badly. He sighed in resignation. “Thanks anyway. I appreciate it, really.”
Gabe gave him a lopsided smile and started attacking his noodles with obvious fervor, despite his lack of need for sustenance. After his discouragement subsided, Sam was surprised to find that he was having a good time. Gabriel was charismatic and joyful, brimming with anecdotes about angels and demons and demigods. He laughed too loud and couldn’t go five minutes without making a raunchy comment. Sam found that he didn’t mind, though, because his usual lunch hour was long gone when they decided it was time to go and rescue Dean and Castiel from each other.
“I’ll keep an eye on your file,” Gabe promised. “And grill your brother for all the dirty details! I can’t wait to see this train wreck happen.”
-------------------------------------
Sam looked up from the newspaper when Dean blew into the apartment like a tornado.
“You’re not going to fucking believe it, but he took me to eat at the building cafeteria. Because he gets free lunch there. I still had to pay for mine of course and they just had this weird crap like hummus and these rice pellet things like you’re feeding freaking llamas.” Dean forcefully tossed his jacket over the back of the sofa, “I’ve never met someone so gifted at killing a conversation. He stared at me resentfully the whole time and didn’t laugh at any of my jokes!”
“Nobody laughs at your jokes.”
“Shut up, I’m hilarious. He’s just more sheltered than a monk and a pain in my ass. Not the good kind either.”
“So, your last match went out with a whimper I guess.”
Dean sighed, “Actually I’m taking him out Tuesday. Show that stuffy bird brain what a date is supposed to be like. Where did you disappear off to?” Sam told his brother about his lunch with Gabriel and Dean waggled his eyebrows suggestively. “Archangel, eh? Aiming high as always, Sammy.”
Sam rolled his eyes and went back to solving the crossword puzzle. This was going to be a treat.
-------------------------------------
Over the next few weeks, Dean took Castiel out on increasingly romantic and resentful dates. Sam rolled his eyes every time his brother insisted that it was just to “educate the asshole.” Sam may have made a snide comment about when Dean was going to move on to Sex Ed and he was met with utter disgust.
“I mean you’ve been on like five dates already, haven’t you at least made out or something?” Sam only asked because he’d never known Dean to go out with anyone he didn’t bang within the first week, not even in high school. He was concerned lest his only sibling had caught some kind of rare disease. Like monogamy.
“Ugh, gross. I wouldn’t kiss him if you put a gun to my head,” Dean said as he packed up a picnic basket for his lunch date.
“Really?” Sam raised an eyebrow and leaned a hip against the kitchen door jamb. “Because I’ve never seen you go to these lengths for a date before. I mean, man, you’re wearing a vest!” Dean forcefully tossed the bag of assorted gourmet cheeses in the basket.
“Oh yeah?” he challenged. “I’m a vest guy now. Ask anyone!” Sam stared at him skeptically.
“Dude, you always said they made you look like a monkey.”
“They make me look debonair! All the chicks dig it.” And Castiel, Sam would bet. Dean slapped the basket lid shut and grabbed the bouquet sitting on the counter. He gestured with it angrily at Sam. “I don’t need any lip from you, what I wear is my own damn business. At least I don’t have long hippy hair and a…stupid nose!”
Sam didn’t even bother to hold back his smirk. Weak comebacks were always a sure sign of Dean getting defensive. Dean stormed off to meet Castiel at the botanical gardens. Out of respect, Sam waited until he slammed the door before he texted Gabriel all the details.
Ever since their lunch together, they met up regularly under the pretense of Gabriel updating Sam on the status of his letter, (it was always, “sorry Sammy, not a peep,”) but really it was to gossip about their brothers and just chat. Gabriel had contacted him first, with a jokingly fearful phone call about Castiel’s “angry falcon glare” following his date with Dean. When Sam demanded to know how he’d gotten his cell phone number, Gabe had appeared on his desk with a quiet pop, pointed to himself, and exclaimed, “Hellooo? Archangel!”
Gabriel had the wildest anecdotes and Sam figured at least some of them had to be true. It got to the point where Sam memorized Gabriel’s elaborate and oddly specific coffee order. He half suspected Gabriel just got it to mess with the baristas.
They met up at their usual coffee shop later that evening. Minutes later, Gabriel was wiping tears from his eyes.
“I can’t believe that mook! He’s gonna wind up proposing to Castiel just to prove a point and my brother’s dumb enough to accept.”
“What do they even do on their dates? I mean I can’t imagine Dean or Castiel being lovey-dovey.”
“I asked ol’ Cas-pants, but he’s tighter than a clam about these things. We should find out, we should tail them on their next date.”
“I don’t know,” Sam hedged, he wasn’t entirely comfortable spying on his brother, but sneaking around with Gabriel sounded fun. Sam hadn’t had fun in a long time.
“Look, you know I hate to brag, but I am an archangel.”
“You’re an archangel?” Sam interrupted with insincere incredulousness. Gabriel swatted at him.
“Like I was saying, I’m all powerful, I can totally hide us so those love-hate birds would never notice.” Gabriel waggled an eyebrow. “What d’ya say, Sam?”
Sam was ashamed of how little convincing he needed and started to form a plan with the devious archangel.
-------------------------------------
Gabriel didn’t understand why he even needed a desk. An office, sure. All important people needed offices. But a desk? He just wasn’t a desk kind of guy. A desk only served to remind him of all his damn responsibilities. Instead, he preferred to think of it as a flat, ineffectual storage space. Whose bright idea was it to make him head of the Cherubim, anyway? Michael got the Seraphim (of course), Luci got the Malakim (that sort of made sense), Raphi got the Watchers (Dad help ‘em), and he got stuck with the love brigade.
Gabriel didn’t even like the whole matching system. It worked for some people, sure, and that was great. Heck, he’d even gotten a good match out of it once with Kali, but that sort of went down in flames (pun intended). What killed him was the rules. They were so stringent, arbitrary, antiquated. Everything he wasn’t. Worst of all, it left people like Sam Winchester all mopey and heartsick. The system must be flawed if someone like Sam was left out.
All the same, it was Gabe’s job to make sure things kept running. He sifted absentmindedly through his inbox, tossing meaningless memos aside -- didn’t angels know how to use email? -- until he came to something that made him pause. It was a large brown envelope addressed to him with the This Is Sort of Important seal stamped on the front. For one panicked moment, he thought it might be a match for him, but all matches were hand-delivered to ensure receipt. Besides, archangel matches required archangel approval, so one of his idiot brothers would have undoubtedly already dropped by to poke fun at him. Maybe that’s what it was -- they’d finally found someone for Raphael and needed Gabe’s approval. That guy could definitely use a good lay. He tore open the folder and scanned the familiar words quickly before his heart stuttered to a halt at the first name.
Samuel Winchester.
He didn’t know why he was so surprised. He’d put a flag on Sam’s file, after all. Just the same, a thick cloud of melancholy descended on his shoulders and his stomach sank knowingly. Of course the first guy he’d been interested in (like, actually interested in, not just a quick fuck, though he’d definitely be open to that, too) for decades would get a damn match. Just his luck. Out of pure curiosity, he scanned the rest of the letter until he came to the name of Sam’s supposed true love.
This time, his stomach didn’t sink -- it attempted to bust through his chest, Alien-style. The letter slipped from his fingers and he immediately dropped to the floor, scrambling to find it. They’d definitely have his ass if he lost a match like this one. It was a mistake, it had to be. There was just no way. He couldn’t subject Sam to... that. But even as he re-read the names, he knew it was no mistake. There were no mistakes. That’s what everyone said, anyway. And, in some weird fuck-off way, it made sense.
Gabriel groaned and slammed his head down onto one of the many piles of paper and candy wrappers decorating his desk. Just his fucking luck. Best of all, joy of joys, he somehow had to give the news to Sam.
-------------------------------------
At eight o’clock sharp, exactly the time they’d discussed, there was an enthusiastic knock at Sam’s front door. Gabriel was knocking out an off-beat rhythm when Sam finally opened it. He could only stare in shock for a few moments.
“You look, uh, interesting,” he muttered.
“I think the word you’re looking for is,” Gabe clicked his tongue and winked garishly, “18 karat.” The archangel -- archangel, that was still really hard to believe -- was dressed in crisp, straight-leg jeans rolled up the ankle to reveal bright white socks and shiny black loafers. He was also wearing a yellow checkered button-up and a bright red jacket that clashed horrifically with the whole outfit. Sam was almost certain there was decades-old pommade combed into his hair.
“That’s two words,” Sam finally pointed out.
“Whatever.” Gabriel shrugged. “I just figured I’d go with the whole drive-in movie theme. Admit it, you love it.”
“Yeah, sure, I love it. I’m this close to throwing on my poodle skirt and doing the Lindy Hop.”
“Lindy Hop was the 30s Sam, get with the picture. The 50s were all about the Jitterbug.” Gabe started flapping his arms in something that somewhat resembled dancing. “Now where’s the poodle skirt? I’m serious here.”
“I am not doing this in a poodle skirt.”
“Well, if you’d prefer to do it out of the poodle skirt, that’s fine too. Just keep the frilly socks, I’m begging you. Such a turn-on.”
Sam found himself grinning stupidly. It was really ridiculous how comfortable he was around Gabriel, even when the topic of conversation was crossdressing and innuendo.
“Fine,” Sam chuckled. “I’ll make sure the socks stay on.”
“But seriously, you can’t go dressed like that.”
“What wrong with how I dress?” Sam demanded, holding out his arms and looking down at his outfit. Just a plain button-up and jeans. Standard.
“As much as I love how shapeless your ass looks in those jeans, if you’re gonna be seen out with me, it’ll be in something more exciting than that.” Gabriel chewed on his bottom lip and looked Sam up and down. “May I?”
“May you what?” Sam asked, raising his brows. Gabriel gave him a ‘surely you jest’ sort of look and tilted his head to the side. Sam sighed heavily and let his arms drop to his sides. “Fine,” he grumbled. Gabriel grinned like it was Christmas morning.
“So glad you said that, Sammy,” he laughed, snapping his fingers. Suddenly, Sam had the strange and unfamiliar of fabric snug around his waist and air around his thighs. He was also holding what appeared to be a pot roast.
“Gabriel,” Sam growled warningly. He wobbled a little in short kitten heels as he attempted to take a step towards the archangel. The floral pastel skirt, frilly apron, and pearls made it slightly less menacing. Gabe laughed uproariously and snapped up a pipe that he clenched in his teeth and blew small, iridescent bubbles out of.
“Careful honey, you’ll burn the roast with that attitude,” he chuckled.
“Change it.”
“All right, all right,” Gabriel groaned, “have it your way.” He snapped again and Sam was thankful to feel denim wrapped around his legs again. He glanced down and noted a plain white shirt, black leather jacket, and short black boots.
“Acceptable,” Sam said with a nod.
“Glad it meets your standards, Princess,” Gabriel replied, giving Sam a sidelong glance that he hoped was subtle. Sam caught him at it and gave him the standard bitch face.
“Now can we go? Please?” Sam drawled.
“Sure thing, kiddo.” Gabriel leaned up and placed two fingers to Sam’s forehead, then came the strange, gut-twisting sensation that came from being angel mojo-ed 30 miles across the county.
-------------------------------------
“So let me get this straight -- you magic’d a car here for us to sit in, but you couldn’t drive it?” Sam drawled, eyeing Gabriel, who was way too into his weird greaser outfit. When Gabe had first showed him to their spying vehicle (he kept calling it ‘Barracuda One’), it was a cherry red Hummer. One look from Sam had made him snap it into a more manageable vintage convertible.
“Why would I drive?” Gabriel replied. “Who even drives any more?”
“Humans drive,” Sam pointed out. Gabriel shrugged and slipped into the driver’s seat.
Dean and Castiel were nowhere to be seen, but Gabriel insisted that they were close by. Sam wondered if he had a tracking device for Castiel or if it was just natural talent. Sam leaned against the side of the car and examined the white leather interior -- a detail Dean would have appreciated -- and a bored teenager passed by with snacks.
“Ooo, popcorn! Sam, get me popcorn.”
“Can’t you just mojo yourself some popcorn?”
“It’s not the same as you bringing me popcorn, Sam,” Gabe insisted, turning puppy-dog eyes on him, complete with a slight lower lip quiver.
“Fine,” Sam sighed.
“Oh, and Jujubes! And Junior Mints! And Sour Patch Kids!”
Gabriel was still calling out his candy demands when Sam turned and started trudging towards the snack stand. He ended up with a large popcorn, sodas, and a sampler pack of movie candies the cashier had recommended when he tried to buy one of everything. He shoved his way back through the crowd, loaded down with way too much sugar, then stopped cold when he came to a sudden realization.
This was a date.
Not lunch, not coffee, not admittedly flirtatious text message gossip. A real, live date. Their second one, actually, if he counted the day they’d met. They might be there to spy on their brothers, sure, but that didn’t change the fact that they were dressed up, in a car, alone together, at a drive-in movie, and Sam had just bought Twizzlers separately because they didn’t come in the sampler pack and he thought Gabriel would like them.
A trickle of cold, nervous sweat ran down the back of his neck. It wasn’t that he’d never dated -- just because he was a romantic about the letter thing didn’t mean he was a monk. He’d dated girls, a couple of them serious, and one guy during college, but he’d stayed away from dating recently in the hope that he’d finally get a match. He just wanted to avoid potential awkwardness.
But despite his best intentions, he’d ended up on a date, a real date, with Gabriel. And he was having fun, and there was this weird sensation that might have been feelings, and shit.
He blew out a breath. He just had to keep his cool. It was nothing, an infatuation. It was fun and easy, nothing that would keep him from getting a letter, nothing that would cause a dramatic scene if it ended. Gabe knew what Sam wanted, after all, and despite his insistence that he couldn’t make the system work any faster, Sam was more confident in his chances with the head of the Cherubim in his corner. Sam felt certain that despite his flirtatiousness, Gabriel had his best interests at heart. His shoulders relaxed and he continued walking towards the convertible. When he appeared with snacks, Gabe made a terribly inappropriate sound.
“Marry me,” he gushed, which made Sam’s face go uncomfortably warm. “Just in time -- our unlikely lovebirds have finally made their appearance. I think they’re arguing about AC/DC. Hard to tell.”
“Here,” Sam mumbled, shoving the Twizzlers and other assorted candy into the angel’s hands. He could feel another bead of sweat trickle down his face. Probably the heat. Definitely the heat.
“Twizzlers!” he exclaimed. “How did you know? Despite popular belief, bribery will get you everywhere.”
“I thought you might appreciate sticks of pure corn syrup.” Sam chuckled nervously, scanning the crowd for Dean and Castiel.
“What’s up with you, Sam?” Gabriel asked, raising a brow. “You’re sweatin’ like a sinner in church. Is it the socks? It’s the socks. I knew it.”
“Yeah Gabe, it’s the socks.” Sam rolled his eyes and slid into the car beside the other man. Gabriel elbowed him in the side, his usual smirk a little bit softer, a little bit warmer than usual, but didn’t press the matter.
“You ready for this reconnaissance mission, Sierra Whiskey?”
“Please don’t call me that.”
“Whatever you say, Sugar William.”
“Just don’t.”
“Desert Fox. Jungle Tiger. Golden Moose.”
“Gabriel.”
“Call me Eagle Panther. Three o’clock!” Gabriel shouted suddenly and shoved down Sam’s head. Which was ridiculous as it just bent him over awkwardly and hid nothing. If anything, it looked like he was doing a ‘favor’ for Gabriel.
“What the hell, man!” Sam sputtered and after a minute, Gabriel let up on Sam’s head and he straightened up. He fixed the archangel with a glare, but Gabriel didn’t seem very contrite.
“Sorry, Laverne and Shirley drifted a little too close to our hideout. They parked a few spots up.” Sam frowned.
“Couldn’t you have just made us invisible? Did you really have to try to put my head in your lap?”
Gabriel slowly looked over at the human and just stared at him and then, like an owl, moved his head back to face forward. It was actually a pretty good Castiel impression, whether intentional or not. Sam decided to let Gabriel’s weirdness slide, he was having a good time otherwise.
He craned his neck to see two figures in Dean’s beloved Impala. They sat at practically opposite ends of the car and didn’t appear to be interacting at all. Disappointing, but not unexpected.
“When will those idiots get a clue,” Sam muttered. Gabriel hummed in agreement.
“It’ll be great to watch it implode. Either they’re going to kill each other or start humping in public like dogs in heat. Considering I don’t think my baby bro is even aware he has a dick, I’ll go with the former.”
Sam didn’t respond, he just watched the pair. Gabriel shifted restlessly next to him like a child who needed to be entertained every waking second or he got antsy. Usually, that kind of impatience would irritate Sam, but it was oddly endearing to think angels were supposed to be these ancient, serene creatures and Gabriel was more like a hyperactive five year-old.
“I think it’s going well, considering,” Sam commented after Dean shifted fractionally closer to Castiel. “They might get there sometime this decade.”
“You really think they’re gonna work out, don’t you?” Gabriel asked incredulously.
“Dean is practically pulling Castiel’s pigtails and I’ve never seen him do this kinda thing for someone even if he claims it’s motivated by spite.” Sam knew his brother better than anyone.
“Whatever. They’re going to crash and burn, the system’s all jacked up anyway. Your brother isn’t the first to get ten letters.” Sam shook his head.
“I’ve seen Dean manipulate it for all it’s worth, but I think it’s finally beaten him in the end.”
“You’re funny, Sam. Why do you want this to work out so bad?” Sam ducked his head and stuffed some popcorn in his mouth. “Oh my God, you think it’s romantic, don’t you? Sam, there is nothing romantic about an arranged match. Love shouldn’t be forced on people, humans are supposed to thrive on free will.”
“You can say what you want, but I’ve seen it work,” Sam began, a bit defensively, “my parents were each others’ first match and I’ve never seen two people crazier for each other, even after years of being together. It might be idealistic of me to hope for something as wonderful as that, but I still want it so bad.” Sam felt embarrassed at how much he revealed, he was usually very private about these things. Something about Gabriel lowered his guard though. The archangel eyed him oddly, and something that looked suspiciously like guilt flared there, but was gone in an instant.
“You haven’t been saving yourself for Mr. Right, have you? Because that would be a damn shame.”
“I’ve dated on my own. My head isn’t that far in the clouds. But, I always felt like, I don’t know, something greater was waiting for me. Like I’d get a letter, meet my match, and everything would just click into place.”
Sam stopped as he realized he was waxing poetic. Dean would have been mocking him a long time ago and he would have expected the same of Gabriel, but he had just observed Sam in contemplation. He seemed disillusioned with the letters. Understandable after looking at it an inch from your nose for centuries, but there was a flame of hope in Sam that couldn’t be doused. Its glow had loomed in the background of every serious relationship Sam had.
He remembered when Jess left him, saying even if everything was perfect Sam wouldn’t have the letter to prove it. He did feel a little regret about that. If he hadn’t sealed his heart like an envelope, Sam suspected Jess would have been so easy to love completely. Gabriel sighed and brought Sam back to the present.
“You’re one hell of a guy. Shine on you crazy diamond and all that. Whoever snags you is one lucky bastard.” For some reason, his voice sounded somewhat sad.
They both sat in silence, half watching the movie. After a few minutes, Sam spoke up.
“Thanks for not laughing at me.” Gabriel scrunched his nose.
“I’ll laugh when you say something funny, Jerry Seinfeld. Now, quit hogging the Twizzlers.”
Gabriel gnawed at the red candy and snuck a glance over at Sam. The big lug was splitting his attention between the movie screen and his brother’s car, probably planning out Dean and Castiel’s damn wedding or something. Gabriel subconsciously touched his jacket over where the inside pocket was.
The letter wasn’t so much as burning a hole in Gabe’s pocket as smolder annoyingly. It wasn’t that he meant to keep it from Sam, he’d just gotten distracted. After all, Sam had brought him enough Twizzlers and gummy bears to dispose of a weaker man. He had an obligation to finish it all. Then there was Castiel and Dean, being ridiculously entertaining. Finally, there was Sam -- Sam, who just kept being so damn thoughtful and cute and clever and sexy as hell just for extra torture.
And... and he just didn’t want to give him the letter, okay? Why ruin a perfect night? Sam and his freaking smarmy-ass prince charming had waited long enough, hadn’t they? Whatever. He just wasn’t great at giving away things he liked. And Sam had -- somehow -- become a thing that he liked, damn it. He’d do it tomorrow. Or the next day. or maybe he’d just give it a week. In case of... something. Gabriel moved his hand to steal a fistful of popcorn from the bucket on Sam’s lap.
Continue to Part Two