DISCLAIMER: I do not own Harry Potter or, sadly, Draco Malfoy. Just borrowing the story and characters from the genius who does own them.
Draco Malfoy was eleven years old. He watched the three friends enviously as they sat at the Gryffindor table, celebrating their victory over his own house. He wasn't envious of the fact that they had beaten him. He was envious of their friendship. He could have had friends like them, if it weren't for his father. Actually, he could have had them as his friends if it weren't for his father. He looked at the wild-haired brunette being engulfed between the two boys and felt a pang of regret that she would never be his friend.
Draco Malfoy was twelve years old. He watched the swotty, confident girl with the frizzy curls deflate before his eyes. He had panicked at her words, and that terrible word that his father had used so much that summer had just slipped out of his mouth. He had never meant to call her a mudblood, and the tears that he could see welling up in her eyes caused an ache in his chest. He looked at the intelligent brunette and felt a pang of regret that she would never forgive him.
Draco Malfoy was thirteen years old. He watched the increasingly confident girl with the crazy curls breathing heavily, smirking as her friends congratulated her. He had never intended to offend her, had only been mocking the groundskeeper to appease his "friends", knowing that what he said would get back to his father. His face stung from where she had slapped him, but he was secretly proud of her. He wished that he could tell her how proud he was of her, but that could never happen. He looked at the courageous brunette and felt a pang of regret that she would never know how much he envied her spirit.
Draco Malfoy was fourteen years old. He, along with every other boy in the Great Hall, stared in awe as he watched the elegant girl with the perfectly tamed curls stroll through the hall on the arm of Viktor Krum. He wished more than anything that she was holding on to his arm. He had wanted to ask her to be his date but knew that, even if he had dared to defy his father and his family name so brazenly, she would never have accepted. He watched her twirl around the dance floor in Krum's arms, watched the dazzling smile that was glued to her face, causing her to glow with excitement and happiness. He looked at the radiant brunette and felt a pang of regret that she would never know how beautiful he thought she looked tonight.
Draco Malfoy was fifteen years old. He watched the powerful girl with the curly hair glare at him in anger as he held on to Longbottom in Umbridge's office. He could see the anger in her eyes as she glared at him. The anger turned to fear and disbelief when Professor Umbridge slapped Harry Potter across the face. She wanted to know something, and it was clear, to Draco at least, that Potter would never tell her. He watched, astonished, as Umbridge readied herself to use the Cruciatus Curse on Potter. At that moment, Hermione spoke up. He listened to her as she flat-out lied to the professor, and his admiration of her surprisingly Slytherin plot grew. He looked at the frightened but brave brunette and felt a pang of regret that she would never know how much he admired her.
Draco Malfoy was sixteen years old. He watched the wonderful girl with the beautiful hair through tired eyes. She was sitting with Potter and Weasley, the latter of whom was ignoring her and ogling Lavender Brown. Draco shook his head derisively. What a moron. If Hermione Granger was his, he would…he sighed, defeated. She never would be his, so there was no point in even thinking about what he would do if she was. She was perfect and clean and unsullied by darkness, and he was none of those things. He rubbed his forearm subconsciously and mourned what never was and what would never be. He looked at the beautiful brunette and felt a pang of regret that she would never know how much he wished he could be good enough for her.
Draco Malfoy was seventeen years old. He watched in horror as the broken girl with the dirty, damp curls lay screaming and thrashing on the floor of his home. He watched as his aunt, Bellatrix, tortured her over and over again, first with the Cruciatus Curse and then with a wicked-looking knife. She was screaming and bleeding, her voice cracking with the strain of her screams, but the torture did not cease. When his aunt moved on to her next victim, he watched as Hermione lay limp and motionless on the floor. She gazed at her bleeding arm with sightless eyes, and her nearly dead stare terrified him. He couldn't bear to think of her as being destroyed and shattered. He looked at the hurting, disheveled brunette and felt a pang of regret that she would never know how much he wished he could have taken her place.
Draco Malfoy was nearly eighteen years old. He watched with weary eyes as the victorious girl with the dirt-streaked face stood with her best friends. He wished he could have been included as one of her friends, but it could never have been. A lifetime of regrets washed over him, and he sank back into the chair that he was occupying, hidden in the corner of the Great Hall. Regret that he had ever been mean to her, that he had called her that terrible name more times than he cared to admit. Regret that he hadn't been born the person that was deserving of her love and attention, deserving of her. He watched as she mourned over each fallen comrade and friend. He watched as she moved through the Great Hall, assisting in healing and comforting all the people in need. He watched as a tired smile would grace her face as she talked to their classmates, her friends. And he watched as she walked toward the doors of the hall with Potter and Weasley and didn't glance his way once. His head dropped down and a single tear slipped from the corner of his eye. He looked at the exhausted but triumphant brunette and felt a pang of regret that she would never know just how much he had always loved her.