It was quite a feat, getting Winona to admit that she was impressed.

But she had to hand it to him, she was most definitely impressed with this one. Ten minutes after she arrived, he had memorized a plethora of her miniscule habits that took a lot of ill-fated dates three days to notice, from her drinking preference all the way down to the color of nail polish she'd been wearing that night. She could venture into shallow territory and ponder his physical attributes after realizing he could hardly constitute as unfortunate looking, but that would be rather boring when there was so much more than just soft eyes and masculine splendor to entertain.

"Give the lady another Cardassian Sunrise…it's on me." Spoke the man, leaning over the bar with what looked to be a shot of bourbon. He glanced over at her, catching a glimpse of the blonde with a hint of nervous flush in his cheeks. "George Kirk."

"How could you tell what I was drinking from the other side of the room?" She asked nonchalantly, draining her glass. His eyes were on her; she could feel the intensity and knew that this one, no matter how hard she would try to screw it up, wasn't going anywhere. From the looks of his pressed Starfleet uniform and the rigidity of his posture, he looked like a man who had never been acquainted with a no-win situation.

"You look like the kind of girl who would have an acquired taste for alien liquor." He took her commentary as a sort of acquiescence and sat down at the bar beside her. "Besides, you're wearing your hair down, which means you're feeling feminine tonight. The short skirt tells me you're not afraid of your sexuality; in fact, you flaunt it to attract attention, but not because you're desperate for it, only because you feel you deserve it. A Cardassian Sunrise is the drink of a woman who knows what she wants and isn't afraid to get it."

"Hmm," she shrugged, and the thought crossed her mind that she should feel at least a little intimidated by such a dexterous set of observation skills. "Alright, I'm impressed. Plus, you're cute. I'll accept. What's the challenge?"

"Challenge?" he smirked playfully, and as she looked at him, she was surprised to find a bashful glimmer in his eye. "Woman, I am the challenge."

She snorted and doubled over laughing, balancing the empty glass in her hand effortlessly. As she regained her posture, she looked around for the cluster of Starfleet uniforms. "Alright hot stuff, who put you up to this? What…am I your initiation? Pick up a chick at a bar and make sure she gets drunk enough for a good lay?" She squinted at him, her intoxication becoming more apparent as the alcohol began to race through her system. "Wait, I've got it," she held up a hand, as if to allay the surrounding noise. "This is a bet, isn't it? Alright…what do I have to give you as proof? A lipstick tube, will that work? Because that's all I've got on me…"

He grabbed her hand as she reached for her clutch. For a moment, as her focus was solely on him, she could see his true nature perfectly clear.

As another moment passed and he did not speak, she found herself bearing witness to the purging of his pretense as it was washed away in the tide of exposure, the farm boy shining through an insipid and poorly conjured mask. Winona never went for the shy guys; it was always the rough callus of the bad boys and the indifference their ideals entailed that left her feeling parched and aching for more. Being so enthralled with the lack of stability in her life seemed to push all possibility of love out of sight and out of mind.

But this one…he seemed to have the word exception written all over him. From the soft, beseeching light of his eye to the small quirk that began to curl at the edges of his lips.

"This isn't a bet. It's not a request for a one night stand and if you think that you know my intentions just because I wear the Starfleet emblem, then you're quite wrong." At last, he let go of her hand and, for once, Winona found herself thoroughly intrigued.

"Forgive me if I sound a little…patronizing, but I know your type...you haven't had the advantage of an easy life. You look for the easy route, but that's not always the answer. Sometimes it takes a little sacrifice to get where you really want to be. And I think that maybe, even though I know I'm not your usual taste, you should give me a chance. If I'm wrong, then I won't even look back as I walk out that door," he sighed and his hands, desperate to release their restlessness, began to fumble with his shot glass. "I'm no Casanova, but I am always right. But maybe...just maybe, I'll give you permission to be the first to prove me wrong."

Again, he paused, and his gaze flickered from the ground to capture hers, unaware of the fact that she heeded his proposition with rapt attention. Winona realized that he was confessing his attraction to her, in his little special way. And that's what he was...special. There was no doubting it now and, seeing as she was never one to doubt anything, there was no escaping the epiphany either.

The bartender slid another Cardassian Sunrise in front of her, but she didn't have the heart to even glance at it, not with such sober honesty before her now. It was much too early to have her heart set on monogamy, but she had a distant feeling, way back in the cobwebbed corners of her mind, that there was a spark. Maybe, it was intended for something more…a slow burning flame, perhaps only one quick plume of ignition.

But she'd never know unless she gave the boy a chance, now would she?

She held out her hand, slightly dumbstruck by the unstable mix of her alcohol intake and the severity of his words. "It's a deal, farm boy. Call me Winona."

He chuckled and rubbed anxiously at the back of his neck, looking up at her through a layer of thick lashes. "Yes ma'am…but only if you return the favor."


AN: I haven't seen any 'first meeting' for Winona and George yet, so I thought I'd add my little two cents as to how I think the events in which James T. Kirks inevitable conception transpired in the beginning stages. Anyway, thanks for reading this short little one shot. I'm hoping to have my full length Chekov fic out soon!

Disclaimer - I own nothing of Star Trek. It all belongs to Gene Roddenberry and J.J. Abrams.