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Jeff Winger doesn’t really like sex. There, he said it, even if it was only in the privacy of his own head. Jeff Winger doesn’t really like sex, has never really liked sex, if he’s honest with himself. (Which he rarely is, but who’s keeping track by this stage of the game?) Jeff Winger likes what he’s supposed to like, has spent his whole life liking what he’s supposed to like, and he’s doing fine. You hear him? He’s doing just fine.
“Yeah, or we could not set all the trashcans on fire,” he says, not even looking up from his phone, and Annie clears her throat.
“Again,” he says, and when Annie smiles at him, he doesn’t let himself entertain a single thought. Fine, okay? Fine fine fine.
Here’s a list of things Jeff Winger does like: most of the stuff he’s not supposed to.
If he’s going to be honest, if he’s got to be, he knows, deep down, that ‘in possession of a balanced mental state’ is not a phrase anyone is ever going to be using to describe Jeff Winger, ex-attorney at law, chaos incarnate, the King of Spades, lord of not giving a shit, He Who Is In Love With Annie Edison.
Yeah, okay, so maybe ‘Annie Edison’ is right at the top of the list, just above ‘Shirley’s pies’ and ‘men, in a sexual way’ and ‘Pierce’s joke, that one time.’ Jeff’s whole life has been spent liking things he’s not supposed to like, and doing things he’s not supposed to do. He was only a lawyer in as much he was a conman; was only on the path to somewhere by virtue of going nowhere fast.
So, Jeff likes Annie, and Jeff’s not supposed to like Annie. So what? Who gives a shit? Jesus Christ on a fucking bicycle, what else is new?
“You aren’t texting anyone,” says Abed, and Jeff can’t even be bothered to sigh, just says, “You know you aren’t supposed to read over people’s shoulders, Abed.”
“But you aren’t texting anyone,” says Abed, and Jeff snorts, says, “No, I’m not.”
“You should just call her,” says Abed, and because apparently Jeff can’t be bothered to do a lot of things today, he doesn’t pretend, “I’m trying for the moral high ground. I mean, I don’t like it, but it’s the thought that counts.”
“No, it’s not,” says Abed, and that’s when Jeff does sigh, says, “Can I ask you something, Abed?”
“If you want,” says Abed, “but sometimes people don’t like it when I answer their questions, fair warning.”
“Do you think trying to do the right thing matters?” says Jeff, and for once it isn’t sarcasm, for once it isn’t an open-and-shut case.
Abed frowns and says, “Define the context,” which really shouldn’t be an answer, but, somehow, it is.
So, Jeff Winger doesn’t really like sex. He likes making out, until it gets to the point where the clothes come off and all the pressure starts up. He likes being naked if no one’s going to touch him, likes people telling him they want him as long as they aren’t going to try and act on any of the things they’re whispering in his ear. Jeff is used to his body being wanted, knows how to use it, knows how to twist the knife so it doesn’t hurt until later, until he’s alone. Jeff doesn’t really know what it’s like to just want to fuck someone because you like them, because they’re hot, because it’s nice and they’re nice and everything could be nicer.
At root, Jeff Winger doesn’t know how to want. At root, Jeff Winger doesn’t know how to be wanted. Sex is all about expectations being met, right? Right?
“You’ve got six of my pens already,” says Annie, and Jeff tries his best rockstar smirk, says, “Make it seven?”
“No,” says Annie, and turns a page in her textbook.
“I’ll give you the money for the alleged previous six pens?” says Jeff, and Annie sighs, says, “Fine. Actually, not fine, I bought a hundred pens in a multipack last week, I’ve got a better idea.”
“Which is?” says Jeff, sliding that smirk back on, and Annie smiles, the smile that means she is about to con the conman, says, “Help me move in my new bed tomorrow?”
“Jesus, Annie,” says Jeff, and Annie smiles again, says, “Don’t even try to tell me that I should make Abed and Troy do it, Troy has football practice and Abed has a film lab all day.”
“Fine,” says Jeff, viciously turning a page in his textbook, and Annie grins, says, “What do you have all that muscle for, it not to use it?”
“Er, yeah,” says Jeff, because she’s not wrong, is she?
Okay, so maybe Jeff Winger liked sex a time or two. He can manage okay if it’s in the dark, and even more so if it’s in the dark and he knows he can leave without saying goodbye. He fucked a couple girls in high school and it wasn’t terrible, but they’d fucked him for his jawline and the fact that he had loner mystique working for him even then. (Friends, though? What friends?) He did it with a dude he met at a bar conference and they never said a word to each other, hands slipping over hotel sheets and there were something in the guy’s eyes, like he was looking at something holy, that, for once, didn’t make Jeff’s skin crawl.
He did it with Britta because he was supposed to do it with Britta, because sometimes he still clings to doing the things he knows he’s supposed to do, even if doing them hasn’t really worked out in his favour. He always made sure she came, he did his best at that, but it doesn’t mean that he did, or even most of the time, really. There was always something in her eyes. It was never enough. He was never enough.
Meet Jeff Winger: when has he ever been enough?
“I bet I can think of a few things to do on this sucker,” says Jeff, petting Annie’s new, and visibly significantly better bed, and Annie makes a small sound of exasperation, says, “Does that really work for you, Jeff?”
“Lots of things work for me, kid,” says Jeff, bringing out the smirk like a shield as Annie sighs, says, “You know, Jeff, I don’t really think they do. I’ve made out with you, remember, I felt the way you got shaky—”
“That was just you, baby,” says Jeff, but his silvertongue isn’t so silver, isn’t so winning, isn’t convincing anyone, even himself.
“Yeah, okay,” says Annie, “do you want some hot chocolate and marshmallows? Troy went a bit crazy at the store, we’ve got enough for a year, or a small apocalypse, whichever happens first.”
“Sure,” says Jeff, because that’s what you do when you get caught, you roll over, you play dead, you wait for your next chance to please, because he’s not enough, he’s never enough, and if he plays dead enough she’ll like him enough to move him slightly above ‘pity fuck’, won’t she? Won’t she?
Jeff has often been a pity fuck; has made a career of it, really. Just because he doesn’t use the patented Ben Chang technique of ‘beg until she caves’ doesn’t mean he hasn’t been doing it for years. There’s something broken in him, and people sometimes see it, sometimes take it out and reel it in and pull him along after them, even if they don’t know they’re doing it. (Britta didn’t know. She’s a good person, and she didn’t know, even if he did, even if he knew all along.)
He’s got the smile and the chest and the jawline and the hipbones and the tongue that can make you come as easy as it can get you off in a whole other courtroom, but the truth of it is that Jeff Winger is rarely fucked by anyone who doesn’t pity him, and is rarely pitied except by those who see his eyes when he just can’t make it to the finish line, no, not even if you put it there, sorry.
The most he can ever wish for is a pity fuck. Hope’s for suckers. Hope’s for people who can meet their own eyes in the mirror. Hope? Is a loser’s game.
“So I’m just going to ask,” says Annie, her fingers tightening around the spine of her textbook, her voice going high and tight, “do you really not like me?”
“Honestly, I don’t know how to answer that without getting punched,” says Jeff, keeping his voice smooth and his pulse steady, and Annie raises her eyebrow, says, “Does that mean no?”
“What do you want me to say?” says Jeff, trying for honesty and landing somewhere near ‘desperate’, and Annie sorts, angry, says, “Whatever you like, Jeff. Is this just not going to happen? Do you really see me as just a kid? Oh, God, was I bad at making out, I was, wasn’t I, oh, God—”
“You were really good at making out,” says Jeff, hurriedly, “but I’ve been talking to my therapist and—”
“You obviously have a lot of issues when it comes to, er, putting your mouth on another person?” says Annie, as Jeff gapes at her, open-mouthed, “Yeah, Winger, I was there, you were a step above my highschool boyfriend in the ‘going crazy in your mind’ stakes.”
“I’m not secretly gay!” says Jeff, and Annie raises another eyebrow, and wow, okay, she really is observant and he really is up shit creek.
“Okay, let me table a motion,” says Annie, smiling, kind and soft and with more than a little steel behind it, “is making out okay? Hands-off-swimsuit-areas sort of thing?”
“I, yeah,” says Jeff, and Annie huffs happily, says, “Eight, my place. Bring Abed’s DVD of Casablanca back, he’s been getting not-cute weird about it.”
“Okay,” says Jeff, because what else is there to say to that, really?
Okay, so maybe Jeff Winger has never had sex with another person and enjoyed it. So maybe he always feels like a piece of meat, because he’s in possession of a mirror and he knows what other people see, when they look at him, knows what they expect that body to be capable of doing. (And if he didn’t, he’d be reminded of it every damn day, anyway.) Maybe he’s never fucked another person without waiting for the judgement at the end, without waiting to be found wanting. (And he is, inevitably, found wanting every time.) Maybe he only really likes making out, or, at least, has so far.
Greendale’s about change. So change it. So go on. Try.
“Milord,” says Annie, and she’s never said it first before.
“Milady,” he says, and he’s grateful that she waits for his nod before she steps in, presses a close-mouthed kiss to his lips. She smells like ink and vanilla and duct-tape (he decides not to ask) and he feels her smile, small, against his mouth.
“I’ve been watching My Little Pony with Abed,” she says, “and we’re going to watch it and make out a little and you are not going to make that face like your hair didn’t look cool for, like, six seconds, okay?”
“Okay,” says Jeff, and closes the door behind him, does not concentrate on how his palms are sweating but his hands are only shaking a little, and it is okay, it is, it is, it really is.