Author's note: 8,000 words of this fic were written post-Season 3 and pre-Season 4. The rest will be consistent with this, making this fic a sort of AU.

Title: Idiots and Lost Causes
Author: wordybee
Spoilers: Up to season 3, I guess.
Rating: T for now?
Warnings: Weird timeline. Swearing. Mopey Jeff Winger.
Word Count: 1,745 for this chapter.
Disclaimer: I don't own Community.
Summary: Jeff and Annie have been in the habit of giving up for so long that neither of them noticed that they never actually did.

There's a glittering diamond ring resting on Annie's finger – not too big, but not exactly a speck of a thing either – and it's with an excited flourish that the twenty-four-year-old announces her recent engagement. Everyone jumps out of their seats and goes in for a group hug, the usual congratulations (Shirley's practically singing them, actually) becoming an indistinct cacophony of words and wordless exclamations that makes the other people in the bar turn toward them. There's a smattering of awkward applause from the more drunken patrons (Do they think we're all getting engaged to each other? Jeff wonders. Why are they clapping?) but for the most part, the strangers seem uninterested in the "good news" and more interested in them no longer making such a scene. Jeff, who's on the edge of the group hug – awkwardly patting shoulders with one hand while his other still clutches a glass of scotch – kind of gets where the angry outsiders are coming from.

When they all (thankfully) settle back down and the glares of the Friday night crowd at Pauline's Pub (pretty new, moderately cool, safe for groups, no hipsters in sight and a good selection of decent drinks; the menus aren't laminated and they use the word 'pub' without irony or tackiness) are no longer focused on the Greendale Seven, Britta holds up her Vodka Neat With Four Olives and says, "To Annie!"

Everyone follows her lead, clinking glasses and taking sips and smiling, and well – if Jeff downs his scotch in one go, it's because it's not on par with his regular stuff and savoring it just isn't on the cards tonight. He makes sure to order something better the next round and surreptitiously texts his girlfriend ('Mary' in his contacts list, but her name is actually Marylou and no one's allowed to know that) and tries to keep the smile on his face.

Hours later, when Jeff is folding himself into the back seat of the cab someone had called for him (maybe Pauline's Pub doesn't have as high-quality liquor as Jeff previously thought, because he'd consumed that other glass of scotch pretty fast, too, and when drinking below-par scotch got to be too redundant Jeff started ordering vodka martinis instead and those weren't that great at all) he reaches into his jacket pocket in an attempt to get at his phone but his fingers touch something else – a napkin, he realizes when he takes it out. It has some writing on it that Jeff's eyes are too tired to read. He shoves it back in his pocket and tries not to throw up, because he hears that cabbies charge you extra if you do that.

The first words out of Jeff's mouth when he gets back to his apartment are "My friend Annie's getting married."

And it's a good thing there's actually someone standing there, because otherwise Jeff would be talking to himself and then he'd be drunk and crazy.

He doesn't seem notice the look of exceptional understanding in Mary-Not-Marylou's dark brown eyes but it's there, because she isn't a stupid woman. Neither is she a malicious woman, nor a particularly jealous woman, or completely blind, or entirely without comprehension of the situation she'd found herself in when they'd met over a month ago.

"Is that so?" she says, voice mild as she pulls off Jeff's coat and drapes it over the arm of his couch. Jeff suddenly seems to realize she's in his apartment, looks around, and goes,

"Where did you come from?"

The truth is that Mary had noticed a sharp decline in Jeff's spelling and grammar in his texts over the course of the night and had put two and two together to equal 'Jeff Winger might drown in his own vomit,' so she took it upon herself to make sure that didn't happen. She'd used the spare key he keeps in the potted plant by his door to let herself in. None of that is worth mentioning to a man who wouldn't remember in the morning, however, so she just says "Montana," and smiles.

Mary leads him to his bed, pulls off his shoes and socks and belt but leaves on the rest of his clothes because it's cold in the apartment and trying to undress and re-dress a 6'5 man-shaped mass of drunken dead weight is pretty much impossible. She pulls the covers around him, fetches a glass of water and two aspirin and sets them on his nightstand, and clunks a small wastebasket somewhere around where his head might end up if he needs to hurl in the middle of the night.

"They have terrible scotch at Pauline's Pub," Jeff mumbles into his pillow.

Mary says, "Funny how you never mentioned that before."

He's asleep by the time she shuts the light off. She's watching TV on the couch until three. As she listens for any sign that Jeff might need her help and half-watches an infomercial, she thinks, It's only a matter of time now.

(This is how they met: Jeff was visiting Annie, who was volunteering at the hospital where Mary worked as a nurse, and he'd suavely introduced himself to the pretty woman with curly golden-brown hair and the nametag with "MARY MASON, RN" etched into it. Mary asked him out without hesitation as soon as names were exchanged, which seemed to throw him completely, and she really should have noticed the way his eyes automatically flicked over to where Annie was chatting with a white-coated doctor, holding a stack of folders in her arms and nodding enthusiastically.

She didn't, though. He said yes, they went for coffee on her break, and something about Jeff made Mary tell him that her name was really Marylou, and that she was from Missoula, Montana.

"Marylou Mason from Missoula, Montana?" he'd asked with a smile.

She laughed about it. She'd never laughed about how ridiculous that was – and yes, people had noticed, and commented, and joked – but she laughed when Jeff said it with that smile.

When the conversation turned to past relationships and availability and whether or not coffee during Mary's break was considered a date, she saw the glint in Jeff's eyes. The little tell he definitely wasn't aware of that just screamed IN LOVE WITH SOMEONE ELSE. Mary had to deal with a lot of stubborn patients and a lot of cagey doctors and she was extremely good at seeing things that people didn't want her to see. She was also extremely good at fixing things and helping people and, as Mary closed herself off from the possibility of getting anywhere at all with Jeff Winger, she sipped her coffee and decided to be his friend instead.)

Jeff wakes up to the bizarre, paranoid fear that he's being tormented by the multifaceted glare of diamonds but soon realizes that it's just his brain exploding from a massive hangover. He cracks one eye open and instantly shuts it again because the mid-morning light flooding his bedroom is like staring directly into the fucking sun and it makes his stomach roll and his head throb.

He pulls his comforter over his head in order to block out a majority of the light pouring in from his window and slowly, slowly, slowly moves into a sitting position. Then he slowly, slowly, slowly opens his eyes and it still hurts, but it's mostly okay. Jeff blearily looks around the room until his eyes catch sight of a great, glorious glass of water (it feels like something large and foul died in his mouth while he was sleeping) that he flails his hands vaguely in the direction of and eventually manages to grasp. He sips the water gently at first, then enthusiastically, and is about halfway through when he notices to two little white pills on his nightstand. He downs them with the rest of the water, feels slightly less like his insides had been carved out and used as shelter for various unpleasant and possibly zombified creatures, and pulls his comforter more tightly around his shoulders as he valiantly tries to stand.

It actually works, though the world lurches from side to side just a bit, and Jeff manages to get to his door and into the short hall and, eventually, into the living room. Mary is sitting in the black leather armchair, reading a magazine or something and circling things with a purple ballpoint pen, and Jeff slumps onto his sofa with all the grace of a beached whale.

"You want breakfast?" Mary asks him, not looking up from her magazine.

"God, please, no food ever." Jeff pulls his comforter over his head and cocoons himself in the glorious darkness of the navy blue fabric.

His voice is muffled when he says, "Thanks."

Mary doesn't ask what he's thanking her for. She just hums an acknowledgement at him and, Jeff assumes, keeps circling things.

(Here's how Mary found out who Jeff was in love with:

They'd known each other for two and a half weeks and Jeff said he was going out with some of his friends from college, and would she like to come along and meet them?

He took her to Pauline's Pub and over to a table where a strangely varied group of people were sitting. When Jeff had said 'friends from college' she'd kind of assumed they'd all be male, Jeff's age, maybe from a Frat or a football team or some Law club or something, but no. There were three that could be no older than their mid-twenties, one woman that was probably a bit younger than Jeff, one woman that was probably a bit older than Jeff, and a man in his mid-sixties, at least. Jeff introduced them all and said, "Guys, this is Mary," and they'd all said "Hi, Mary," like it was some bizarre AA meeting.

One of the women – Annie, the young brunette with a grin so cheerful and bright it could rival the sun, who looked very familiar but Mary couldn't place how right then – laughed and said, "I could've brought Vincent along if I knew it was Couples Night!"

Jeff's grip on Mary's hand tightened and he huffed out a laugh that sounded less like a laugh and more like a man who'd just been punched in the gut. He said, "Yeah, totally," and Mary had a face and a name to put with that big flashing sign of unrequited love emblazoned across Jeff Winger's heart.)