Disclaimer: Me no own Community. Me stupid.

A/N: This is my first ever attempt at fanfiction of any kind, so please be gentle with me!

It started in his first semester at Greendale. A tiny ache in his left side arrived so suddenly, it stole the breath from his body and coherent thought from his brain. It came fleetingly after that. Every now and then Jeff cursed inwardly at all the wrong turns and bad choices he ever made which led him to this place, to this moment, to this pain.

He tried not to think about it and, mostly, he was successful. Jeff Winger had the kind of first rate brain that could compartmentalize things like feelings and morals, truths and lies, and so pain was just another label to put on yet another box.

But then the years passed and the pain became more frequent and less fleeting, more dominant and less dormant, until the box burst at all corners. And when the crap tumbled out and into all the other neat compartments, all thoughts were tangled like the twisted web of wires behind his TV. And now, most days, his brain was dangerously charged and if he attempted to touch all these things; to push back all thoughts and feelings, truths and lies, he was sure he would get some kind of electric shock.

And so now, there is a pain on his left side that just won't go away. She sits there with her head down, a purple pen pursed between bubble-gum pink lips and oh my god the pain. Does she not realize what she was doing to him?

Above the edge of his Biology textbook, he studies her for a moment more. A shiny shard of chestnut hair has fallen over one creamy shoulder. She's wearing the same dress she wore to Troy and Abed's house-warming party months ago; a floral strapless thing that is somehow indecent now that she's discarded her cardigan. The fact that he knows this – that he remembers what dress she wore – is part of his problem. And also makes him a giant pussy. When did he become such a girl?

She looks so bouncy and youthful and happy and if she were just that list of simple adjectives he doubts he would even be in this predicament, wading through these dangerous waters. But outwardly, Annie Edison may appear naïve and innocent and fresh and unbroken but he knows she isn't. He could add so much more to her list. And therein lies the bigger part of his problem.

He shouldn't know that Annie is tougher than she looks. He shouldn't admire the strength behind those beautiful blue doe eyes of hers or know that he couldn't match it. He shouldn't know that she's bursting full of passion beneath those prim colourful cardigans and that she waits for someone to give her permission to unleash it all. He shouldn't secretly want to be the one who does it.

He knows Annie Edison because, in many ways, she is just like him. She is as selfish as he is (and actually quite good at it now) and just as competitive. In different ways, she's as driven as he can be. Britta scoffed at this but heck; he didn't become a damn fine lawyer by sitting on his ass. The degree might have been fake but he wasn't. He steered that courtroom in the direction he wanted. See? He was driven. In your face, Britta. In. Your. Face.

The fact is he shouldn't know all these things about this girl – this woman – who, at twenty-one, stands on the crest of her future; whose life lies untainted and full of potential. It's just not right.

Because he is mid-thirties and jaded. He has a long list of exes; ex-girlfriends, ex law firm, ex lawyer, excuses. He has things like laughter lines and a credit history dating back to when she was probably six years old. As much as he hates to admit it, he has a lot of issues that can only be dealt with by his therapist. He has already half lived his life in a tainted sort of way. He isn't even sure if he has a future and the only potential he has is taking steps backwards. And then where would they be?

It's not like he wanted to know her. He didn't ask to; she invited herself, remember? He was quite happy to charm her with a few 'Milady's' every now and then; to receive double-spaced notes with a smile after class. He was ambivalent generally; her fawning over Troy didn't bother him. It was Troy and she was eighteen and that's to be expected. Right? Anyway, he had Britta to chase and that was challenge enough to consume his time at Greendale.

But somehow he got bribed to help win a debate and Annie let her hair down and thrust her cleavage in his face and oh my god the pain. As he connected the dots between Annie and sexy and beautiful, Annie was very swiftly placed on his radar and that was dangerous and wrong. And so another box opened and she was filed away, and with it he stuffed down his awareness of her.

But all the while he dashed and delved between Britta and Slater, and Pierce's step-daughter and that student's mom he couldn't even remember the name of now (though he knew he slept with her twice, oh yeah), Annie was there on the periphery. She was his Ace news-hound and returned his googly eyes across the table. She broke him with the Disney face and dressed like a Professor (and he knew why, could she be any more obvious?).

In front of him she nearly stripped off her clothes over a lost pen and just the thought of it made his breath rise and filled him with panic. He wasn't sure why. She shot him with a gun and looked at him under the blankets as if she was mesmerized and he still can't remember ever having as much fun as he did that day. And when she kissed him he dropped humans on hard floors and made him forget the chaos and bullshit that two hot crazy women created in one night.

And worst of all, she knew how to kick him when he was down. She knew his weakness to her tears, his embarrassment over old audition tapes. She knew how he worked; could detect his bullshit faster than anyone, saw the cogs working overtime in his brain, and only had to subtly raise her eyebrow to force his hand. She knew that telling him she didn't want to be his friend was the worst punishment in the world.

Just as he knew her; every crazy, adorable, beautiful facet of her, she knew him. And it terrified the shit out of him.

With Britta it was easy. There was no stomach-lurching fear there, the kind that made him run out of rooms or say inappropriate comments at model UN's. Sure, Britta was guarded. And yes, she took a while to succumb to the Winger School of charm but that had been the delicious part of it; the chase. He knew she would surrender eventually. He thought how great it was having her ride him on the study room table while the others fought a messy paintball war outside. They had built to that moment, as explicit and carnal as it was, from the beginning. Worth it. Britta was hot and sexy and had no expectations. It was one of the reasons why he had sex with her for nearly a year without anyone realizing; without all that other bullshit interference. Britta fitted neatly in a box. He knew where he stood with her, where they stood with each other. She didn't expect love or commitment, or hallway hugs and kisses, hand-holding under tables or stolen moments in supply closets. She didn't expect him to be better than he was. She understood him for what he was now.

Who was he kidding? That was then. Before Greendale and the study group attached themselves like six extra limbs, before a brown-haired blue eyed girl looked him in the eyes and asked him to feel.

And he didn't want to feel, not at all. But Annie did something to him. Somehow she had mined her way into him, found a crack in his walls and seeped through until he could feel her as a constant presence, a thorn in his side. He dreamed of her in song and she danced before him in a sexy outfit and wore tight sweaters and somewhere along the line, when he wasn't watching, she grew up. And now the lines were blurred and he was running out of excuses. And if he was honest which, let's face it, was a rarity, Jeff wasn't sure he wanted to make excuses anymore. He was tired of keeping Annie at arm's length when all he wanted to do was close the gap. And if doing so gave him some kind of electric shock like he feared, what if it turned out to be the good kind? What if he turned out to be the best kind of shock he ever had?

He came to the realization last night watching TV with Troy and Abed. Sprawled out on the sofa behind the two men watching Inspector Spacetime, he was about to make some excuse and head to the nearest bar when Annie arrived home. Her face lit with a smile when she saw him and his stomach lurched as if at sea. Only she had the power to do that. She dropped next to him and he felt his heart in his ears, neck, the tips of his fingers. Her soft thigh pressed against his solid one, her scent assailed him, palms began to sweat. He knew it then.

And as Annie looks up at him now, he stares back at her forcefully; there's no point pretending he didn't just get caught looking at her above his textbook. She's stolen one of his trademark smirks and plays with it on her own lips, her eyes awash with a delightful gleam that screams lust and sex and 'I know what you're thinking, Mister!' She glances down quickly, a shy blush tints her cheeks but it's too late. He's even more certain now. The thought forces a smile.

Whether it's wrong or inappropriate, it is going to happen between them. The question isn't where, it's when. He supposes he has Abed to thank for a lot of things…