He had never been there before, but he wanted a place where his friends wouldn't think to find him. He was something of a loner, and had not been able to connect with really...anyone in his life. The people his age were idiots, the men were cruel, unpredictable, and base, and his mother, loving as she was, just did not seem to understand anything he went through. She turned a blind eye to the activities of her husband and pretended that they made their wealth legitimately, and that her precious son could grow up to be anything he wished. She had always encouraged him to dream big - doctor, lawyer, composer. He had enrolled in college, and tried to attend, but he had begun to discover that his father had no intentions of letting him become anything other than the next don. The result was confusion his entire life, confusion which had only recently resolved, and left him with bitterness. Bitterness so intense that he had considered ending his own life.
The young man had always helped his father out, as far back as he could remember. He had even killed a few people, and those deaths haunted his every waking and sleeping moment. He had argued ineffectually with his formidable father, and with his uncles and cousins, who were also in the business. It stayed in the family, and the thought that he should go off to get a master's degree was unthinkable. He did not need to study or work hard. His future had been provided for, they insisted. He did not know how to resolve this issue, and he still felt confused, not able to separate what was the genuine love of his family, and what was control.
So he escaped to the bars, where his usual game was to sulk and drink until he felt numb and aggressive, and a woman who was both good-looking and not too talkative asked him if he wanted to get out of there, and he did. But if he was not careful, his friends (who were all just about invariably his cousins to some degree) would find him. The boys would be entirely uncouth and embarrass him with the way they hit on women, and slap him on the back when all he wanted was to be left alone. His female cousins would shriek giggles and bombard him with questions and whiny requests. A couple of them, he was sure, had crushes on him, and he would rather forget the time when he had felt desperate enough to take his second-cousin up on her offer, and now he had to avoid her like the plague.
Tonight, for whatever reason, he sat at the bar and faced the other way, looking out at the occupants while he drank his whiskey. It did not take him long to notice the girl. She was very conspicuous, the way she occupied a booth by herself, and continually turned away prospective suitors. She caught his eye not necessarily because she was the prettiest girl there (even if she was) but because she was obviously picky. This was something that Nick identified with. He could control so little of his life, he was choosy with his women. He wished he could be more choosy, and turn beautiful women away just so that he could say that he had actually been able to reject something, however difficult it had been to do so. But he was a man, and a lonely one, and he had needs. So he envied this stranger her pickiness which exceeded even his own.
Furthermore, she presented a challenge, a test, and that appealed to him, as well. He was born into his legacy, he had not had to earn it. He wished he had, for then he could flunk out of it. He had no opportunity to test the mettle of what he was made of, to succeed on his own in the world. He was usually overshadowed by his loud family, and his accomplishments, which would be valued in the world, were useless for their internal nature in the life he had been set into. Each time this girl turned away a man, Nick felt his competitiveness rise a little higher. His desire to succeed with this woman began to feel like lust, although it was not. He was hungry for a test.
He enjoyed watching each man approach her, and guessing whether he would be the one she would accept or not. His guess was usually no, and those guesses were always right. This shored up his confidence, and finally, he approached her himself. Once he began moving, edging his way around the outside of the packed room, he became more noticeable. He did not act, look, or dress like anyone else there. He looked far more like a scholar than a gangster or a clubber. He had very dark brown shoulder-length hair which had a slight wave to it, and turned into a few scant, messy curls about his fine-featured face. Round, thinly wire-framed spectacles sat upon his nose, over light brown eyes. His mouth was thin-lipped and turned down in a perpetually speculative look. He wore a rumpled white shirt, beneath the collar of which was looped a skinny dark-grey patterned tie. Over the shirt he also wore a vest which was a lighter patterned grey. Narrow dark grey slacks and polished black dress shoes finished off the ensemble.
Nick was immaculate, yet mussed. Handsome, yet nerdish, in a grown-up way. He was tall and thin, and only slightly muscular. He looked the opposite of what he was slated to be: a thug. He was son of the don, used to money, women, and drugs, but he had a brilliant mind and a driven nature. He wished to see if he could pass this woman's test, and yet, he did not yet know if she would pass his own.
He stopped at the table, his nearly-empty whiskey glass brought with him, for something to do with his aristocratic hands. His nimble fingers rested the bottom of it against the tabletop, comfortably, although not setting it there as though he presumed to stay. His other hang hung casually at his side while his bright eyes met hers, and as his head tilted, the lighting in the club made his glasses go momentarily opaque. He did not try to artificially force that unimpressed mouth to form unnaturally into a smile, though his gaze somehow seemed friendly, or at least, curious.
"Do you want to be left alone?" he asked, the idea only just now having occurred to him. It almost made him blush, the thought that he had concocted this elaborate game for the woman, only to realize at her threshold that perhaps she wished to drink undisturbed. It was just like him to be half fumbling over himself, although he seemed nonplussed by his own lack of grace. He was confident in who he was, which was both attractive and slightly alarming. His eyebrows were raised over his large eyes, the surprise at the externalized thought evident. "If I had realized, I would have sent you a drink from over there."
There was no irony in the words. Also, it was worth noting that the question was not an invitation for dismissal, or a precursor to defeat. Just a request for more information, so that he knew how to proceed. He had an air of emotional detachment typical of a particularly logical mind, and yet he somehow also managed to give the air of a sensitive soul, whether he was or not. Smooth as he could be, he really had not much experience picking up a woman intentionally, as he usually let them come to him. The result was a great deal of self-assuredness, but not much technical skill in the matter.