Title: Always a first Time

Author: Mindy

-x-

Refrain

The first time he seriously considered kissing Liz Lemon came as a surprise to both of them. It was perhaps not the first time the idea had flitted across his brain, but it was certainly the first time Jack had ever truly considered acting on such an inscrutable impulse.

It was a day full of firsts. When he asked Lemon to attend Gerhardt's birthday party with him, she'd really made him work for it. He'd anticipated that though -- nothing with Lemon was ever simple or easy and he'd pre-prepared a rebuttal for every single excuse she might proffer. He'd instructed Jonathon to verify her schedule so he knew she was free. He made sure to invite her on such short notice that she wouldn't have the chance to freak and back out. He'd organised the dress, jewellery and car. All he needed was Lemon's consent.

To say he was apprehensive about asking her would imply that there was any doubt about the outcome. And to say that he invited her purely for her own betterment would only be half the truth. He truly had wanted to spend an evening with Lemon – he'd wanted that for longer than he cared to acknowledge, even to himself. So, he really wasn't all that bothered that he hadn't had to work so hard for a date since he was a teenager.

The first time Jack saw her in the red dress, he was more than impressed, and didn't bother to hide his surprise. It wasn't so much what the dress did for Lemon as what Lemon did for the dress. He knew when he selected the garment with her in mind that the shade would suit her colouring and the cut would both disguise her imperfections and emphasize the natural endowments she generally hid too well. But he truly hadn't suspected that Lemon had been hiding all those curves beneath layers of navy and denim and spilled food, not to mention a perpetual aura of ragged frustration.

Obviously, he was better than even he knew – and had been paying very close attention to his new protégé. If he were a better boss and less of a man, he would not have spent such time or thought noticing and cataloguing those endowments. Or imagining how she might best accentuate them. But, even in the presence of true inelegance and estranged femininity, Jack was still a man. And part of his duty as a mentor was to develop the particular gifts of each charge.

As it turned out, he could probably have done without the extra accentuation of Lemon's particular gifts. It proved to be a minor distraction that night and more than a little confusing.

He'd tried to delude himself into believing that it was simply the style of the dress that made him want to trace her exposed spine with his fingertips. That it was purely the snug crimson which taunted him into wanting to cup that pear-shaped bottom with both hands and give it a good squeeze. And it was really just the expensive jewels surrounding her pale neck that gave the illusion of Lemon's face lighting up and her eyes twinkling.

It was towards the end of their evening together that it occurred to him that perhaps he'd created an alternate universe Liz Lemon. A woman more accessible, a woman more acceptable -- and it was she who had him falling. It was the Liz of the red dress, the Liz with the diamonds, the Liz who looked almost normal guzzling thousand-dollar champagne by the glassful -- it was she who had him so dazzled and intrigued and slightly disconcerted.

It was party-Liz who was turning his whole evening upside down. The mascara and the heels and the hair had thrown him temporarily, but it was simply an anomalous, transitory attraction. He'd fallen for it before, that mysterious, midnight haze that women could weave around a man's mind with mere feminine tricks of the trade.

Applying such logic to Liz Lemon, though, seemed nothing short of preposterous. There was absolutely nothing about Lemon that was intentionally seductive. If anything, she did all she could that night to keep him at arms length, if not farther. While he was purposefully and covertly seeking to lessen the gap that had always separated their worlds, Lemon was fighting to keep them firmly where they were – safely in the realm of professional friendship.

With all the Bianca business, she was supportive and patient and as a companion she was, as always, entertaining and surprising. But she also made it perfectly clear to him in her own inept way that she was highly uncomfortable with even the idea of anything developing between them.

Lemon's undisguised disinterest, though, only seemed to increase her inexplicable appeal. Jack genuinely hadn't planned to make any move on her when he'd asked her out. But he had to admit to being slightly disappointed by her overly obvious reluctance. Perhaps even a trifle affronted by her barely hidden repulsion.

He usually didn't have that effect on women. He usually didn't hesitate to make a move. And usually, he never doubted the response he would receive in return.

But then, he was usually not interested in women like Liz Lemon. He usually didn't have the chance to get to know her type. He was usually not alone with them, escorting them home after what he considered to be a very successful, very enjoyable evening. Not that there was much about Liz that he would ever class as usual or typical.

Still, when they'd reached that titillating moment of the evening where such moves were made, he felt vaguely illequipped. They'd never been alone like that before and he'd certainly never looked at Lemon the way he found himself doing. He'd never imagined seeing her as more than an acquaintance, more than an employee, more than a slightly frumpy, weirdly amusing writer-type with a special talent for dysfunction.

But there was always a first time.

The relaxed rapport they'd fallen back upon dried up within a millisecond and he saw the uncertainty surface in Lemon's eyes once more. She didn't break the moment or move away. And for a second, Jack simply allowed himself to see her, to really see her -- and to like what he saw.

It occurred to him in that moment, rather unexpectedly, that Liz Lemon was a woman he could truly fall for. That maybe he was halfway there already, without even realising it. And, even more disturbingly, maybe she could detect the truth of it in the flicker of his eyes.

So he stopped, he hesitated. He didn't kiss Lemon.

Even though he'd wanted nothing more. Except perhaps to peel off that devilish red dress, whisk her up in his arms and into the bedroom he knew was just next door. But at the very last moment, Jack refrained. Talk about inscrutable impulses. He'd settled instead for leaning in close and stripping her of her second-hand jewels, his fingertips brushing her skin for the barest moment.

Divesting Lemon of the necklace did not diminish her appeal in the least. It was not all the trappings that he'd forced on her that had produced this effect on him. It was not the borrowed jewellery, the knock-off designer dress or the hasty hair-do that had somehow made Liz Lemon his type. He really was not that susceptible or stupid. Those things had only allowed him to see her differently for one night. The trimmings just acted as a device to draw her closer to him and he wasn't sure he'd ever look at Liz Lemon in quite the same way again.

He would simply have to confess it -- to himself, at the very least. He liked her. Really liked her -- a woman in her late thirties, an egghead, a geek. A wreck of womanhood with poor eyesight, an eating disorder and a big, brazen mouth. He more than liked her -- he wanted her, he adored her. He was utterly entranced by every word, act or deed that tumbled so erratically out of Liz Lemon.

Yet, he'd still hesitated to make a move. It was only as he was walking away from her apartment door, smiling with the perfection of his last quip, that it hit him what he'd done – or rather, what he had not done. Never before had he left a woman's place without getting precisely what he wanted.

And Jack wanted Liz Lemon.

Lord, did he ever. He'd wanted her more than he could ever remember wanting another woman since his tyrant of an ex-wife. But, for some strange reason, he'd stopped himself, second-guessed himself. Jack Donaghy, confirmed ladies man and risk taker extraordinaire, had backed down, chickened out, bailed and run.

Surely, there was a first time for everything.

TBC…