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.