Six years after his first class at Greendale, the only proof that Jeff Winger was ever a lawyer was in his closet. Suit jackets and pressed shirts hung in one corner, expectant—as though any day, he would tire of his life as a poorly paid professor.
But it had been a long time since he’d wanted to go back. It had been a long time since he’d thought he could.
Each morning, he reached past those jackets and dress shirts in favor of a sweater, or perhaps a polo. Something comfortable.
Because somehow, over the span of six years, he’d become a man who dressed based on comfort.
Who would have guessed.
Teaching at Greendale wasn’t an ideal, either, but after six years, he was willing to acknowledge – at least to himself – that he stayed because it was easy. Because he knew what to expect.
He used to say that he stayed because of his friends, but after Troy—after Pierce—after Shirley—after Annie and Abed and Britta were all gone, he found that that had become quite a flimsy excuse.
After they were all gone, he lost track of how long it had been since he was a lawyer.
Semesters rolled by and Jeff taught because it was easy. Contact with members of the study group dwindled, and he learned not to be sad about it.
He stopped pulling out gray hairs when they came in (wherever they came in). He bought reading glasses and, eventually, he was even willing to put them on when there was someone else in the room. He dated age-appropriate women, although it never lasted too long.
He stopped seeing phantoms of Troy, Abed, Britta, Shirley in the grocery store, or in the next car over.
Sometimes he still thought he saw Annie, but he became better at ignoring that.
Jeff had settled. Jeff had settled hard.
He didn’t mind.
One Saturday morning, around the middle of December, he was out doing his weekly grocery run when he thought he saw her poring over the ingredients of the name and store brand soups. He nearly texted her to joke about it, but that felt intrusive.
He thought he saw her again in the dairy aisle.
And then she saw him picking out wine.
“Haven’t you always been more of a whiskey guy?”
Jeff almost dropped a bottle at the sound of her voice. “Tastes change.” As he turned to look at her, he gave her a careful once-over—less appraisal, more curiosity.
“You don’t, though,” she said, gently. Her eyes sparkled.
He swallowed this comment as best as he could. “You do. How long have you been wearing your hair like that?”
She shrugged. “About a year. I had an undercut for a while, but I decided to lose it, so I had to cut it pretty short. It’s been coming back alright.” She tilted her head to the side, just slightly. “It’s good to see you.”
“It’s good to see you, too, Annie.”
Thank you, he didn’t say, for not pointing out my salt and pepper hair.
She was home for the holidays, and she’d come out to the grocery store because her parents did not want to go. This was, of course, her primary responsibility. Jeff had no interest in fighting for her time when her parents were home waiting.
“—but maybe I can come over tomorrow evening and we can catch up?”
Well. She didn’t have to ask him twice.
Jeff didn’t love Annie anymore but it was hard to remember that when he was getting dressed the next day. He reached past his old suits and grabbed a sweater that he hadn’t worn in years.
It was blue, soft. It had always been her favorite. Every time he put it on, a warm memory hit his gut of the time she fell asleep with her head buried in the crook of his neck while he was wearing it.
So he’d stopped putting it on.
Annie brought over a bottle of scotch, “because tastes don’t have to change that much.”
She told Jeff about the FBI and he listened, he really did. He even tried to tell her genuine stories about Greendale when she asked him about his world.
But he also saw a glint of something familiar in her eye as she looked at him.
Perhaps Annie could tell Jeff was wondering, because she said, “I broke up with this guy like four months ago and it’s been impossible to find a date since. I hardly ever meet new people, and I refuse to shit where I eat.”
Jeff almost coughed into his drink. Part of him, he suspected, would always be surprised when Annie swore.
Even with the knowledge of her singlehood, Jeff did nothing. He put down his glass after one drink and he sat back and… listened.
“I think I was wrong,” she told him. “You have changed.”
He didn’t argue.
Annie set her glass down and kissed him and he didn’t argue.
It was strange, how she could taste, kiss, smell, feel just the same and so different, all at once. Jeff ran his hand down her side and he was struck by how toned she felt, solid beneath his grasp where she had been so slight before.
But one thing was quite different—
Neither of them seemed inclined to stop with a kiss.
Jeff knew that he would wake up the next morning, and for countless mornings afterward, having to purge the Annie from his system once more, but that didn’t stop him from lifting his arms when she tugged his sweater up.
As he kissed her neck, Annie let out a mellow sigh and mused, “Your stubble’s a bit scratchy,” and he had barely any time to stumble through an apology before she breathed, “No, it’s wonderful, please don’t stop. I haven’t dated anyone with a good beard since I left Greendale.”
He didn’t know quite what to make of that, so he kissed her harder.
They could have stopped when Jeff practically fell off his sofa. But Annie looked at him for a moment before murmuring, “Can we… I mean… your bedroom…”
Jeff used to imagine what sex with Annie would be like.
Everything he’d imagined had been wrong. They touched each other like it would kill them to let go for more than a few seconds, but they moved… so slowly, the evening stretching before them as one endless world of possibility.
He felt in his gut that she would never touch him again and it only made him hold her closer, kiss and touch her more reverently.
Annie straddled Jeff and trembled over him and, when they were both satisfied, she closed her eyes and laid on top of him like this would be her final resting place. Her fingers in his hair and her head buried in the crook of his neck.
“Why did you do this?” he finally allowed himself to whisper.
Her breath was soft against his ear. “I guess I just… I saw you yesterday and realized that it was like I said to you, before I left. I’d regret it for the rest of my life if I didn’t.” A slight pause, and then, even quieter: “Why did you?”
“I don’t know.”
This was not true, and he knew she probably knew it. But she was gracious.
She got up to pee eventually, and when she came back, she was more gracious still. “Do you mind if I stay here tonight?”
Jeff lay with his eyes closed, his covers up past his waist. His heart pounded in his throat. “Nah.”
“I’m going to borrow something to sleep in, if that’s alright.”
He opened his eyes just a crack, unable to resist the image of Annie in any of his clothes. “You’re welcome to anything.”
And then she was reaching into his closet and pulling out one of his dress shirts.
Jeff sniffed just slightly. Remembered the man he was when he met her.
“I have changed.” He echoed her words from earlier, to the ceiling more than to her. “You changed me.”
She climbed in beside him and rolled onto her side to look at him. To scrutinize him. “I’ve been gone for five years.”
He didn’t answer at first. He didn’t answer for a while, until after she’d leaned over him to turn off the light.
“Your absence changed me.”
Annie might have been asleep, and Jeff found that if she was, he wasn’t particularly bothered. Maybe she was older than she once was, but she didn’t deserve that weight any more in that moment than she ever had.
Hi this wasn't going to have a second chapter but I just rewatched the show over the course of a week and a follow-up from Annie's POV was nagging at me.
Since returning home for vacation, Annie had been unable to shut off her body’s natural urge to rise early, and that morning was no different. She blinked awake to the utter darkness of an unfamiliar bedroom, and it was the smell that told her where she was, a good ten seconds before her memory caught up.
She found it oddly reassuring that, however else he had changed, Jeff still smelled exactly as she remembered.
She had no clue where her phone was, and she didn’t want to rummage around for it for fear of disturbing Jeff, but she was willing to chance a guess that it was a bit after 6:30 based on the slight hint of light peeking in through the blinds.
Beside her, Jeff snored softly. Years ago, this would have been a source of great vindication for Annie—she’d always been convinced that he must snore, and he’d always denied it.
Now, though, it just made her feel… sad, mostly. She couldn’t shake the feeling that something had ended.
It wasn’t that Annie had always assumed that she would sleep with Jeff someday. Maybe she did while they were at Greendale, but she left for the Academy knowing full well that she’d closed that chapter of her life.
And it stayed closed, it really did, but there was always a part of her…
She’d return home for holidays and she’d imagine that they’d run into each other, and in those daydreams, they always fell into bed. It wasn’t an active expectation or even much of a passive longing, but she held onto the image in a way that she didn’t hold onto much.
But Annie’s imagination had not covered the part that came next. So much so that she didn’t really know what should come next, even though she certainly should have figured it out before going over to his apartment.
She didn’t notice that Jeff’s snoring had dissipated until, in a low, gruff voice, he mumbled, “I forgot how loud your thoughts are.”
Annie continued to stare at the ceiling because Jeff was lying on his back, too, and she didn’t know how vulnerable he was going to be. No matter how good she’d gotten at reading him, she’d never known quite how vulnerable he was going to be. “Sorry. You should go back to sleep.”
“I’m not tired.” Jeff hesitated. “I could make you breakfast.”
“I’m not hungry.”
This was true, because Annie usually didn’t eat a full breakfast until after working out in the morning. But there was a part of her, too, that didn’t want Jeff to get up and make her breakfast because she knew it would catapult time forward and in seconds, she would be leaving, she would be back in Quantico, she would be past this, and she didn’t want to be.
“How do we always end up this way?” she breathed.
“What way?” he asked, and Annie couldn’t blame him for sounding genuinely bewildered.
She squeezed her eyes shut and inhaled deeply. “Trying to freeze time. That’s… that’s what it always was between us.”
From the corner of her eye, she saw Jeff turn his head to look at her, and the rest of his body followed. But she was too scared to look at his expression as he said, “I’m not trying to freeze time.”
Hadn’t it always been about that? About Jeff’s longing to stay young. About Annie’s longing to feel safe enough somewhere that she could allow herself to stand still.
“I’m trying to feel every second that’s ticking by.”
Annie swallowed. “Oh.” She considered this for a few moments before asking, “Why?”
“Because this is a once in a lifetime thing – don’t try to tell me I’m wrong,” he chided as Annie opened her mouth to interrupt. “I feel like if I’m willing it to stand still, I’ll miss it for what it actually is, I guess.”
“Which is what?” Annie whispered.
“Something very complicated.”
They both allowed those words to hang in the air for some time until Annie exhaled slowly and rolled onto her side to face Jeff, allowing herself to meet his eye.
“I’m turning 30 on Saturday,” she told him.
“How does that feel?”
Annie sighed. “Completely unremarkable. But it… it’s gotten me thinking.”
Jeff raised his eyebrows. “Dangerous as it sounds?”
She scoffed and punched his chest lightly with her fist. Allowed her skin to linger against his for one heavy moment. “No. I just…” She swallowed. “Right before I left Greendale, Frankie told me that by the time I hit 30, I’d be glad nothing ever happened between you and me.”
“Oh.” Jeff’s eyes widened.
“Yeah, it was pretty harsh,” Annie said, offering him a gentle smile. “She was kind of right, though, in a way.”
Annie paused, but either Jeff thought she was going to go on, or he didn’t know what to say, because he just blinked at her wordlessly.
“I didn’t date at Greendale after Vaughan left. I mean, I wanted to date Rich, but let’s be real, my crush on him had a lot to do with the fact that he was a more well-adjusted version of you.”
“Nice to hear you say it,” Jeff said, smirking.
“Whatever,” she scoffed and rolled her eyes, but she continued to smile warmly. “My point is that it didn’t matter how many times we said nothing would happen between us, because I left the option open anyway. Part of me didn’t ever want to see that door fully close.”
Jeff’s Adam’s apple bobbed as he swallowed. “Okay. But what does that have to do with what Frankie said?”
“I mean, let’s be honest, you would have been an awful first adult boyfriend. Especially the way you… the way you used to be.”
That, right there, was the real clincher. Annie imagined this Jeff strolling into their Spanish class all those years ago – this Jeff who had no dishonorable intentions when she walked through his door, this Jeff who approached sex with the express intention of making her happy – and she knew that a relationship between them would have been a fling, but God, would it have been a good one.
“But I’m a good late 20s last hurrah,” he murmured. He didn’t sound hurt, exactly, but there was an emptiness in his tone that gutted Annie to her core.
“No, that’s not exactly how I’d put it.”
Jeff hummed. “Alright, how would you put it?”
“You’re just…” Her heart beat rapidly in her chest as she traced over everything that had ever happened between them, all in the span of a second. “Something very complicated.”
“Touché,” he whispered.
Silence fell between them again, but they continued to look at each other. Thin lines of light were beginning to spread across the bed and across Jeff’s face, but he did not shut his eyes or move an inch.
Annie nearly didn’t say the words that came out of her mouth next, but she blurted out the offer before she could convince herself against it. “Speaking of Saturday… We’re going out for drinks. You should come.”
“Yeah, y’know… Britta, Shirley, Abed, Troy… to celebrate my birthday and Troy’s homecoming. I wasn’t sure whether to invite you after I found out…”
After she found out that Jeff didn’t keep in touch with anyone else from their study group, not really. Not beyond obligatory happy birthday texts. Annie had told herself, when they ran into each other, that she would ask why, but now, it felt unreasonable.
“But you should come,” she said lamely. “I think they’d all love to see you.”
He stopped abruptly when she reached up and rested her hand on his jaw, lingering there.
“Jeff,” Annie retorted, her tone low and kind and, she supposed, as reassuring as she intended, because his features softened. “What makes that so different from this? Couldn’t seeing them also just be about… how did you put it? Feeling every second that ticks by.”
In that moment, Jeff looked more like the man she used to know than he had since she’d run into him at the grocery store. He looked torn and nearly ready to close himself off to her and Annie half-expected his next words to be, “No, now please leave.”
But instead, he said, “It’s easier for all of you. You have somewhere else to go, but for me…” Jeff squeezed his eyes shut and sighed. “Annie, this, right here, is the first time in years that I haven’t felt like I’m standing still. And you’re going to leave and it will be hard, but I will deal with it. Just don’t… don’t ask me to look at how fast they’re moving, too.”
Annie brushed her thumb along his cheek and imagined the old Jeff making some excuse about why he couldn’t show. She would have fought with that Jeff.
Not this Jeff, whose eyes were still closed so that he didn’t have to look at her.
She leaned over and kissed him, soft and slow and neither of them deepened the kiss, but she lingered so that he could feel every second of it. And then she climbed out of bed.
“Let me know if you change your mind,” she told him as she picked up her clothes and dressed.
Frankly, Annie did not expect a response, but Jeff gave her one anyway. “Tell them that Greendale misses them.”
Annie nearly crawled back into bed with him at these words. She imagined herself staying with him all day, staying past her vacation time, staying forever.
Maybe she hadn’t changed as much as she thought she had.
On Annie’s 30th birthday, Jeff woke up unnecessarily early. It was anxiety or anticipation or both, and neither feeling seemed justified when he knew nothing would come of it. He was going to spend the day alone.
In a past life, he’d have dealt with those feelings by exercising excessively or drinking inappropriately early in the day. But that was a different version of Jeff Winger—this Jeff Winger went domestic. He cleaned his apartment, started his laundry, cooked and froze some meals for the coming week.
Annie texted him an address and time at 11:17 AM, then texted him again less than a minute later.
Still hoping you’ll come around.
He didn’t reply, but her words rang through him as he went out to do his grocery shopping. Each time he turned a corner, he found himself wondering whether she would be there, and it wasn’t until halfway through the trip that he realized that, somewhere in his gut, he kept hoping the answer would be yes.
Sorting his food onto the conveyer belt, pulling up to the ATM to withdraw some cash, picking up a library book he’d reserved, putting away his groceries—still hoping you’ll come around.
It seemed heavy in a way that he knew it wasn’t meant to, just like everything had always seemed heavy with Annie. If he’d learned anything from the transfer dance all those years ago, it was that they both needed to be damn certain about what was going to happen if they were going to consider dating for real.
Even at his most certain, it had just not felt like enough.
The thing was, though… in the years since Annie left Greendale, he’d had enough semi-functional relationships to learn that maybe one of his problems with Annie had been that he was never going to be certain about how a new relationship would unfold.
One of his problems. Because that was certainly not the only problem.
But as he scrubbed at his hand-wash only shirts, Jeff dared to wonder whether it was a good enough reason to let Annie disappear from his life again now.
That line of thinking was probably how he found himself loitering in a CVS around the corner from the bar Annie had directed him to, approximately 15 minutes after she told him they’d be there. He’d been pretending to dither over trashy tabloids for at least 20 minutes while trying to decide whether to go those final few hundred feet.
He wasn’t sure whether he wanted to talk himself into or out of it.
Britta’s voice was so embedded in his memory that he knew it was her before he even turned to look, so by the time he met her eye, he’d put on his best surprised face. “Britta? Wow, this is… weird. It’s good to see you.”
“It’s good to see you, too! God, it’s so weird that you’re here right now—I was on my way to meet the rest of the old study group for Annie’s birthday when I saw you through the window.”
“Oh yeah, it is Annie’s birthday, isn’t it?”
Britta either believed his bluff or was kind enough to go along with it. “Yeah, I’ve been so busy that it kinda snuck up on me too. What about you, what are you doing here?”
Jeff pulled a lie out of his ass easily. “I was supposed to meet a friend for dinner nearby and I was waiting for them here. But he just texted me to cancel before you walked in, actually, so I’m thinking I should just go home.”
“Don’t you dare,” Britta exclaimed immediately. “Come join us!”
Understandably, she misinterpreted the reason for Jeff’s reluctance. “Look, if you’re worried it’ll be weird for you to just show up… it won’t be. Everyone will be excited to see you.”
He almost turned her down.
Instead, he found himself trailing behind Britta as they moved toward the exit together.
“By the way,” she said, a smile in her voice. “The silver fox look is working for you.”
Jeff actually meant it when he said, “Thanks.”
Even so, he almost turned and high-tailed it out of the bar as soon as he spotted all his old friends together. They would have had a perfectly good time without him.
Then Annie spotted him and her eyes widened slightly, and the corners of her mouth quirked up into a soft smile, and Jeff propelled himself forward.
Her text echoed through him again: still hoping you’ll come around.
“Look who I found on my way here!” Britta announced as they reached the table. “He was around the corner at CVS licking his wounds after his friend bailed on their dinner plans.”
Abed, Shirley, and Troy erupted into a chorus of greetings, but all Jeff heard was Annie’s quiet, warm, “Hi, Jeff.”
“Hi,” he said, to her alone.
When Britta found him, the possibility had lurked in the back of his mind that she knew he had been invited, but now that he was with the rest of the study group, he could tell they had no idea. They were apologetic about his not being invited and it wasn’t awkward but their lack of consistent contact hung over him anyway.
Meanwhile, Annie was certainly pleased he was there, but he couldn’t shake the feeling that she was appraising him.
He couldn’t blame her.
They ordered a round of shots in honor of Annie, but for much of the evening, Jeff nursed a single beer—he was only halfway through his second bottle when Shirley decided to call it a night. Not long after, Troy and Abed decided to split an Uber home.
Jeff lingered, because he wanted to and because he felt like Annie wanted him to.
For whatever reason, Britta lingered too.
No, not for whatever reason. Jeff knew she was just trying to catch up with some old friends. It wasn’t her fault that he and Annie were both keeping something very large from all of them.
He was five minutes from taking Britta’s presence as a sign that he and Annie should not talk, a sign that he should leave and pretend that he hadn’t been so close to making a complete fool of himself.
“I think it’s time for me to head home,” Annie announced.
“Ahh, no, Annie.” Britta pouted, but she moved on quickly to, “Do you want to at least split a cab home?”
Jeff almost laughed in surprise as he realized his luck. “I could drive you both home. I’ve barely had anything tonight.”
“Oh yeah, I noticed that.” Britta squinted at him. “Why?”
“I dunno.” Jeff shrugged. “Just didn’t feel like being in a fog tonight.”
For a brief moment, he allowed himself to meet Annie’s eye.
The drive to Britta’s apartment felt agonizingly long. She was drunk enough not to question whether it made more sense to take Annie back to her parents’ place first, which was good, because Britta lived far closer to him than Annie’s parents did.
She eased out of Jeff’s back seat with a cheerful farewell, swearing that they were going to find some time to hang out someday soon.
Neither Jeff nor Annie spoke at first, but even after Britta had safely made it inside, Jeff found himself unable to pull out of his parking spot.
“They didn’t know you invited me.”
“I didn’t want them to feel sorry for me if you didn’t come.” Annie turned to look at him and even in the dark, her frown was clear as day. “I honestly didn’t realize how much I wasn’t expecting to see you until you came in.”
“I like to be unpredictable.”
Annie hummed. Carefully, she said, “I don’t think that’s what it is, though. I think I just keep forgetting how different you really are.”
Jeff immediately felt too seen, too vulnerable. He took the car out of park quite abruptly and pulled out of his spot, heading toward Annie’s.
Surprising himself, though, he went along with her. “I’m trying,” he said, softly. “It’s a hell of a lot of work.”
“Do you think it’s worth it?”
“It might be.” Jeff swallowed hard. “I’m taking you home now, and I know you’re leaving right after Christmas, but what if… what if I visited you in DC some time?”
Annie’s eyes were on him, although he couldn’t gauge her expression because his eyes were on the road. “Will this be a friendly visit?”
Quietly, he told her, “I’ll come however you’ll have me.”
This sank in, and Jeff let the silence hang until Annie smoothed her hand over his arm and said, gently, “You’re welcome any time.”
Before climbing out of the car, she gave him a parting peck on the cheek.
He had no clue what was going to happen next and somehow, that was completely fine.