A/N: I don't own anything, especially not the characters, which are all the property of the Sherman-Palladinos. sadly!
Firsts
He would never forget the first time he saw her. He walked into that classroom king of the world, fresh from several days off to visit his grandfather, enjoying the notoriety from his excused absence and the admiration of his peers. It was good to be the king, even of such a small kingdom as Chilton. But in the next moment he was stunned, shocked even. Those eyes! Her blue eyes nearly pinned him to the wall for several seconds, until she turned away. He almost didn't notice how beautiful she was, he was so distracted by her eyes. He managed to respond to Romy's question about his grandfather, turned on the charm that made the teachers love him and the girls want him, but nearly his entire concentration was on her.
He asked Josh "Who's that?", unable to hide his interest, but realized in time his mistake—he was the king of Chilton, he didn't fall for girls, girls fell for him. He had a rep to protect, and to do that he had to think of her as just another conquest. So to the answer, "New girl", he responded with "Looks like we got ourselves a Mary!", but inside he was already planning how to meet her. Maybe he could offer to help her study? That would be a good way to get some time with her, to find out if her eyes were really as blue as they seemed, to see if she found him as intriguing as he did her. No! He was the king of Chilton, he didn't find girls intriguing! He just needed to spend time with her to get her out of his system, that was it. He jumped up when the bell rang, eager to find a way to meet this blue-eyed new girl He waited outside, heard Romy tell her to borrow someone else's notes. The fact that he had been away and didn't have notes for the past several days was immaterial to him, so he offered to study with her—offered the way the girls at Chilton liked, with a clear invitation to much more than studying.
Her response shocked him- the blush, the stammer, the "studying as a solitary activity." He couldn't even be upset that she had refused him, he was so disarmed by the way she had done it. He knew then, deep down where he couldn't even admit it to himself, that she was going to be different—that she could change him. But he didn't let that change him. He treated her just like any other potential conquest, he teased and taunted her, he got on her nerves—he gave her his attention as best he could, the only way he knew how. He realized now that she would never have responded to that, even if she hadn't had a boyfriend. But back then, back when she was the first girl he had ever really wanted, and the first girl who hadn't wanted him, he couldn't understand why she hadn't fallen all over him. Why his teasing hadn't been taken as loving. Why every time he got her attention, he also got her anger. He had to admit, she was beautiful when she was angry- he would also never forget the first time she really let loose, the day of the English test when she screamed at him and at Paris—but he wanted to see her in the grip of other passionate emotions. He wanted her to care for him, to want him, to—it was hard to even think it—to love him. The brief flashes of her sympathy and understanding that he had, before they kissed at Madeline's party and afterward when they agreed to be friends, began to show him that she needed something real, something different form the king of Chilton. He had never been that person, he had always been the cool kid, the one who knew all the moves. He tried to be real, tried to get her to like him—he found out music that she liked and got tickets, hoping that she would come with him, and that away from other people she could see the real him, could look at him the way she had looked at that boy at the dance. And he tried to protect himself, he couldn't let her refuse, it was too important, so he didn't really ask—and she didn't hesitate to refuse.
The fact that he loved her burst upon him in a blinding flash on the day his heart was first broken. Before her, no girl had mattered, he had never been emotionally involved. And he had pretended, even to himself, that she was the same, that his near obsessive interest in her was nothing more than chasing after the one-who-got-away, until he heard her say "I hate him." He had never realized he could hurt that badly before. He loved Rory Gilmore. And she hated him. It was a near physical pain, he wanted to yell, to cry, to hurt something, anything. But he couldn't do anything, he couldn't change her mind and he obviously couldn't be the kind of man she wanted. So he gave up. He gave up hoping, gave up trying, gave up caring. When Duncan and Bowman had begun to invite him out for their hijinks, he went- why not? There was no point in being a good boy, she didn't want him when he tried to be one, his parents didn't seem to care. So he went deeper and deeper, and he ended up in military school. Thinking back on it, he was almost glad—he had been too far gone in anger and hatred and self-pity to deal with seeing her, and at least away from her he had been able to deal with his emotions. The school had a shrink and mandatory counseling, and after a few months of trying to get expelled, he finally began to talk. He came to understand why he had done what he had done—and why she and his father and Paris had done what they had done. That school had been the best thing that ever happened to him, although he was sure his father would never understand why.
He had avoided Hartford after that, afraid that to see her would ruin all of his hard work, would unsettle and destabilize his precious mental stability. The shrink had disagreed, had said that he should see her at least once, should apologize, should try to end things on a positive note. But he couldn't bear the thought of her indifference any more than he bore the thought of her hatred, and he stayed away. He even chose Yale because he knew she would go to Harvard, and when he heard from Paris that she hadn't, he planned his courses around what she wouldn't be taking.
He might have known that state of affairs couldn't be maintained for a full four years.