When Jeff really thinks about it, on those days he's feeling light and drunk and happy, he maybe flirts with the thought that, hey, yeah, maybe he's going to be fine.
It's been more than five years since he was disbarred; five years since his career went down the drain; five years since he discovered that he had no real friends or no real life or no real morals to go by.
It's been more than five years since Jeff Winger first stepped onto the grounds of Greendale Community College, getting off of his shiny silver Lexus with a pair of Ray Bans slapped over his eyes. He remembers having hatred and frustration pouring out of his every pore, remembers hating his life, hating his so-called friend who made him lose his job, hating his school, hating every single damn second of being there.
But now, though…
Now Jeff is forty. And Jeff has friends he actually likes, an apartment he could barely afford, a teaching position he isn't really qualified for but he actually enjoys, a school that's become more than just a school, and…
He looks around the study room and his gaze falls on Annie, chewing thoughtfully on a pen as she stares down at her fluffy purple binder.
He remembers Racquel, and, well.
And maybe there's Annie.
::
He doesn't really take his eyes off of her after the play's ended, because she may have smiled and laughed and teared up at little throughout the show, but Jeff can san see the sadness there, a certain weight on her shoulders keeping her down and barely afloat.
She tells Chang she's jealous in a soft voice that's just loud enough for the whole group to hear, and when he glances over at her, she's smiling a little sadly as she watches the cast of the play leave the room in a happy cloud of a job well done.
Except her smile is fading and now she just looks sad, and really, Jeff doesn't surprise himself anymore when he finds himself walking over to her, gently knocking his elbow into the soft pad of her shoulder.
He doesn't even hesitate for a minute, and he isn't exactly sure what this means.
"Hey," he says, following her gaze as he swallows thickly. "I know this great bar for people that don't hate themselves." He smiles down at her, watching the way the corners of her mouth turn up as she huffs out a tiny laugh, and it's—it's not much, but it's a start. "What do you say?"
He holds out his arm, and he tries to ignore the way his heart starts picking up the pace, hammering and clawing against his chest in a way that doesn't feel unfamiliar at all but feels expectedly frightening, all the same.
His mind flies back to three months ago, in a dark, dank bunker where he hooked himself up to an old machine and made it come to life with a lingering whisper of a fond memory.
So he says to Annie, "Milady," and waits.
She glances at his arm, and there's hesitation there, he can tell—but there's also the beginnings of a smile that soon turns into a pretty grin he knows so well.
He expects her to just smile up at him and lead him out of the theater with her hand tucked safely in the crook of his arm.
So when she rolls her eyes and laughs out, "Milord," in a fond, familiar, happy voice, his heart maybe kind of does embarrassing somersaults.
He thinks back to that moment in the bunker and that fleeting memory of him and Annie from five years ago, standing in front of the gymnasium steps as she smiles up at him and uses the term of endearment he hasn't heard from her in a very, very long while.
He isn't sure exactly how he feels, but he thinks it's something almost like fondness and hope.
::
He brings her to a small, secluded bar somewhere in the middle of their neighborhoods.
It's not one of the "better" bars he used to frequent—it's smaller, quieter. The lighting is yellow and dim, throwing a hazy, almost intimate cloud over the room that Jeff likes. It smells like beer and aftershave and wine, and old 80s music plays in the background, low and almost faint above the buzz of conversation. Jeff's been coming here by himself for so long that he's now friends with the sixty-year-old bartender, and he's practically claimed a spot at the bar to himself; he just really finds this place homey and familiar, and Jeff likes it that way just fine.
He and Annie sit at the bar at his usual spot, sitting not too close but close enough that their arms are brushing, and Jeff likes it that way just fine, too.
::
He flags down his bartender buddy, Andy, and orders a scotch and an appletini.
Jeff doesn't even flinch when he does, and when Annie smiles, looking pleased, he tries to ignore the swooping sensation in his stomach.
::
They end up making up stories about the other people inside the bar.
"Okay, look," Jeff says, discreetly pointing out a tall, middle-aged blonde in a business suit, "she's definitely a shady lawyer."
"You would know what that looks like, wouldn't you?" Annie laughs.
"Well, duh," he says, grinning down at her. "I recognize a ghost of my past when I see one."
Annie smiles down at her lap, then gestures at the woman again with her drink. "And who's that she's with?"
"Her equally shady client who's trying to get out of a DUI." Jeff glances at the dark corner of the room where the couple is now sitting—not too close, but close enough. "And there's definitely some attraction going on there."
Annie wrinkles her nose and frowns at the now-shady-looking pair. "You think?"
"Oh, yeah," Jeff nods, looking all knowing and authoritative. "The way they're sitting, with their heads so close together? Who could not see it?"
She tilts her head to the side, her frown deepening. "I don't see it."
Jeff brings his glass to his lips and says, "You will," before he takes a sip.
::
When the woman and her companion share a kiss over at their table, Annie groans loudly, and Jeff laughs as she slaps a five dollar bill on the sticky bar top almost reluctantly.
"I can't believe you were right," she grumbles, looking dejected. "I hate being wrong."
Jeff smiles softly, sliding her money back to her with a shake of his head as he nudges her shoulder with his. "It's okay to be wrong sometimes, you know."
She sighs, swirling a finger along the rim of her cocktail glass. "I know, it's just…it's hard sometimes."
"Knowing it's hard to admit you're wrong is okay, too," he tells her gently.
Annie takes a deep breath then, still staring intently at her drink, and she doesn't look at him when she says, "We're not talking about the shady lawyer and her date anymore, are we?"
"Maybe," Jeff says, downing the last of his drink and sliding his glass across the bar for a refill, "maybe not."
She smiles a little.
He leans in close. "Up to you."
::
It's an hour and a half later when they watch the couple leave the bar, their eyes lingering on the way the man has a hand on the lower part of the woman's back as he holds the door open for her.
Annie sighs.
"I can't believe I'm jealous of Chang," she says, her voice soft, and Jeff thinks she's comfortably buzzed, now on her third drink (a scotch), and he places a hand on her shoulder to steady her. "What is there about Chang to even be jealous of? Even Frankie knows he's unstable."
He senses there's more, so he says nothing, just choosing to squeeze her shoulder comfortingly.
"I just…the director said that I was no good…to my face." Jeff watches her face crumple a little, and his other hand tightens around his glass. "And I just realized that I'm almost 25 and I'm only halfway close to getting my degree…and I'm still stuck at Greendale."
He swigs another mouthful of scotch and swallows thickly. "I'm stuck at Greendale, too, you know," he says, trying to adopt a good-natured tone.
She winces. "I didn't—"
"It's okay."
"It's just—" Annie glances at him, her eyes huge and sad. "If everything had just gone according to plan, I would be taking my master's at Yale by now. You know? Most of the time, I try not to think about these things, but sometimes it really hits me hard that, I don't know. I'm stuck in this life."
Jeff just watches her, his eyes never leaving her face. "Are you unhappy?"
"No." She sighs again, turning back to her drink. "I am happy. I mean, I have you, and Abed, and Britta, and Shirley, and Troy, if he ever comes back home… I just can't help but wish that there could be more to my life than this."
Jeff nods, because he understands, because these are thoughts he's had in the last five years, more times than he can count. Thoughts he still has sometimes.
"There still could be, you know," he murmurs, wrapping both his hands around his glass as he mimics her stance and turns to face the bar. "Want to know something someone once told me?"
She looks at him carefully. "What's that?"
"That it's okay to eat failure for breakfast." Jeff shrugs. "That we can't let something like failures, or the fact that life does suck sometimes, stop us. If I had let every single fucking bad thing that's happened to me—and believe me, there's been a lot. If I had let any of that stop me, I wouldn't even be here."
They're quiet for a very, very long moment.
"It's okay to be bad at some things," he continues, his voice quiet. "Makes us human, you know?"
She's watching him intently now, and there's something in her eyes that he doesn't understand. "Jeff…"
"Also," he murmurs, looking down at her as she meets his gaze. He smiles at her and feels—he just feels. "You're Annie Edison. You can do anything you set your mind into."
A small smile breaks across Annie's face as she laughs and gently pushes his shoulder with a warm hand. "I wasn't fishing for that."
"You know, I've lied my way through life," Jeff says, and his heart is starting to pound against his chest again, "but I'm not lying about this."
She looks down at her lap with a shy smile. "When did you get so…"
"Amazing?" He smiles when she rolls his eyes. "Can I let you in on a secret?"
"Always."
He leans towards her and she follows his movement until their faces are a breath away. "It was actually Pierce who taught me that."
She stills, and he's still looking at her face carefully, and he watches the way Annie's eyes soften, the way they start to fill with tears. He's just about to tell her to stop when the next thing he knows, he's got his arms full with warmth and softness and brown hair and creamy skin.
"Thank you, Jeff," she mumbles, her breath warm against his neck, and Jeff smiles, his face buried against her shoulder as he breathes her in.
He wonders if she can feel his frantic heartbeat, because he can feel hers, and he realizes he isn't even sure which heartbeats are which anymore.
It's like they're beating together.
::
Andy walks up to him after Annie's excused herself to go to the ladies' room.
"Who's your friend?"
Jeff laughs a little at his drink. "That's Annie."
"Oh," Andy says, nodding. "Annie. That Annie." He grins at Jeff. "Took you a while. Would've thought you were better with the ladies that."
"Shut your face," Jeff grumbles, but he's not annoyed, not really.
Andy looks at him a little knowingly. "You've been coming here for a solid year and half now, Jeff, and I've been on the receiving end of one of your many drunken spiels too many times."
Jeff groans, running a hand across his face. "I don't want to hear it, Andy."
Andy raises his hands in friendly surrender. "All I'm saying is, man, you've never once brought a girl here before."
"So?" Jeff frowns. "What's your point?"
"I'm not sure," Andy laughs. "There's just something different about you when you're with her, that's all."
Jeff watches him walk away in silence, his drink forgotten.
::
When Annie comes back, she smiles up at him, and his heart is racing, and everything just shifts.
::
An hour later, they're just sitting in silence, all space and distance between them now gone, as she leans her head against his arm.
There are only a handful of people left in the bar, and Andy's a few feet away, cleaning glasses and starting to tidy up.
It's long past midnight by now, and they've long since fallen into a comfortable lull of silence and familiarity, and he should probably be taking her home, but neither of them mentions the time nor makes any move to leave.
Her hand's wrapped loosely around his wrist, and he watches the way her fingers dance along his skin, making him feel warm and flushed, like he's got an itch somewhere he needs to scratch; he thinks her hand looks so small and soft and delicate against his own.
It's times like this that he wants to say something, like he's been wanting to do for the past three months.
He wants to say things like, I saved Greendale because of you, or I was wrong and an idiot to push you away, or I might be kind of in love with you—and maybe it's taken him three months to come to terms with it, but after that epiphany in the bunker, maybe now he just knows that this is how he feels.
Annie brushes her nose against his arm as her fingers tighten around his wrist, and he lets out a shaky breath he didn't know he was holding.
"Annie," he says, and he hates the way his voice does nothing to hide the sudden terror he feels.
Her voice sounds contented and sleepy. "Yeah?"
He swallows, and it would be so easy.
But it's also so incredibly, terrifyingly difficult to say.
Instead he presses his mouth to her forehead and lingers there for a long moment. He hears Annie suck in a breath, and he feels her other hand travel up his chest to take a hold of his shirt.
It takes him a long time to pull away, and he maybe isn't quite so ready to tell her in words yet, but maybe he's trying to say something in the way his lips touch her skin.
He knows it's not enough.
When he leans back, Annie has her eyes closed, her hand still clutching his shirt as she breathes deeply, in and out, in and out.
He just watches her, not knowing what else to do.
Then Annie raises her eyes to his, and there's a smile on her face as she leans forward, resting her head on his chest as she slides her hand down his wrist and entwines their fingers together.
He lets out a deep breath, rests his chin on her shoulder, and concentrates on her breathing against his collarbone.
It's keeping him steady, somehow, and maybe for now, this is enough.
::
She's slumped over in the passenger seat, her face turned away from him as she watches Greendale fly by outside the window.
Moonlight streams through the glass in streaks of white and yellow, falling softly across Annie's face as she sits there in comfortable silence, and Jeff watches her, fully aware of how his heart works furiously against his chest, his throat, his wrists, his neck…he feels it all over his body, beating wildly and uncontrollably, and maybe he's done trying to deny it.
Annie glances back at him, and his breath catches when she flicks her eyes upward, warmth and softness and curiosity and hope, all blended into a beautiful shade of blue.
She smiles at him, and he feels the world fall back into its axis.
::
Yeah, he thinks, as he takes a deep breath and reaches across the console to put his hand above hers, as she lets out a sigh and turns her own hand over to wrap her fingers around his.
He's maybe not quite so ready yet, but he's getting there.
And Annie's here, humming under her breath, smiling at him, her hand in his, making him feel light and drunk and happy.
Yeah, he thinks. Maybe he's finally going to be fine.