He ten when he first caught sight of her, his father pointed her out murmuring in his ear "Draco, you see her? The blonde girl, by the wall? Go talk to her.", he'd responded with a spoilt "Why?" turning his attention to the girl. She was short for her age, with rich golden blonde hair, worn loose around her shoulders, her face twisted with boredom. His father's response, "Her father's important, her family's rich and she could make a useful connection in a few years. Go talk to her!" had caused him to examine her more closely, however he saw nothing that encouraged him to warm to her, she wasn't in his opinion pretty, she looked bored and she had no apparent interest in him, also she was a girl and his ten year-old self had found the prospect of befriending her intensely unappealing.
So, he'd nodded his assent to his father and continued to enjoy the party, keeping half an eye on the girl to make sure his father didn't approach her, as he'd progressed around the party a boy his own age had approached her, made some comment or other and her face and been broken by a blinding smile, a smile he was suddenly desperate to have turned upon himself, he began to approach her but she laughed at something the boy said and allowed him to pull her away. He looked for her the rest of the night but she was always disappearing in a different direction. That night he cried himself to sleep for the first time he could remember.
He was twelve and in his second year of Hogwarts, the Chamber of Secrets had been opened and he was declaiming that "Mudbloods you'll be next!" when he heard and angry noise and noticed a first year girl glaring at him. His laughter faltered as he recognised her. With a cold glance she walked away. He tried to go after her but his friends (cronies) were watching him so he let her walk away. He looked for her later, asked questions, searched but failed to find her. He barely slept that night, remembering the anger in her eyes.
He was thirteen and he was enjoying the worship in Pansy's eyes as he bemoaned the injury his arm had suffered and declared the dangerous nature of hippogriffs. A voice interrupted his tirade with the words, "Grow up, it was barely a scratch" he looked up complete with sneer, expecting a one of Potter's friends, and a pair of blue-green eyes looked down at him as she sneered right back at him. He froze, his sneer dying and she walked away. He lurched to his feet managed to call out wait, she glanced back with a raised eyebrow and he just shook his head, collapsing back into his seat. He was too scared, him! When Pansy asked him if he was okay he snapped at her and walked out of the hall. He walked for a long time, regretting the contempt she held for him.
He was fourteen and was designing a badge in the safety of his common room, ready to undermine Potter, when a voice interrupted their discussion with "Do you have nothing better to do?" he was half horrified, half delighted when someone near him answered with "Get lost Greengrass", he knew her name but getting a smile from her seemed less and less likely. He glanced up but she was already walking away, shaking her head.
He spotted her mounting the stands to watch the final task, weeks later, and followed her, throwing himself down near her, and heard her scream when Potter returned with Cedric's dead body. The sound echoed round his head the whole summer, reinforced by his inability to help.
He was fifteen and he began to find her attractive in more ways than one. He spotted her laughing with a boy from her year, his arm round her and felt an overwhelming, unexpected anger. Before he could stop himself he'd approached and demanded an explanation, the lazily raised eyebrow and cool "excuse me?", reminded him that he was nothing to her and he backed away, determined to change that fact.
He saw her again leaving Umbridge's office, presumably from detention, rubbing a bleeding hand, he'd stepped out, grabbed her hand and dropped it when he saw the cause of the blood, staring at her in horror. She'd looked back with angry pride and he'd stepped out of her way, let her go past without an offer to help or an apology. He regretted that most of all.
He was sixteen and his life was falling apart, he couldn't cope and she walked in as he wept into a mirror, she'd reached out to him, sympathy in her eyes, and understanding. He'd pushed her away, ashamed and added that to his reasons to cry.
He was seventeen, caught up in a fight he didn't want to be part of, he'd been rescued by Potter and Crabbe was dead, his world had fallen apart and he didn't know what to do next. Then he heard a scream that was shockingly familiar, and sprinted towards it. He found her pinned by two people his father had called friends, people he'd known all his life. She was still fighting, despite a cut running deeply down her cheek and what looked like a broken arm. One of the death eaters raised his wand, his mouth forming the killing curse and he didn't hesitate to raise his mother's wand to a man he'd respected all his life. As the man collapsed her curse hit the other and she turned to him, a smile on her lips, "you chose right in the end, then" he tried to answer but all he could see was the smile finally turned on him. She laughed slightly and reached out her hand to him "I'm Astoria, shall we start over?"