Vampires remember everything. Or at least the real ones do. So when he tries to pinpoint the moment his fascination with Elena became about Elena rather than Katherine, he can flick through his memories like videotape.
He can remember the precise expression of fear on her face when she ran away from the crow in the graveyard. The sound her hand made the first time she slapped him still rang clear as a bell in his memory. The expression on her face when he found her in the car wreck... the first time in over a century that someone had looked at him, knowing everything he was, and been genuinely glad of his presence. The way she had said his name... like everything would be okay because he was there now. No lust, no jealousy, no spite, no sarcasm. Just real 'Thank God you're here'.
But that wasn't it. That wasn't the moment... it was long before that. It was that night in the kitchen.
She had invited him in. And he'd played trouble maker. Damon Salvatore always got what he wanted. So he got inside Elena's house... and he smiled because it pissed Stefan off, and if that wasn't the best form of pleasure available to him in this one-horse town then he didn't know what was. And then he caused... he brought up Katherine. He made Stefan's date as miserable as he could... and Oh could he ever! There were implications behind every word he said and Stefan's caveman brow grew more pronounced by the syllable.
And then he saw the glass. And because he was Damon Salvatore, and he never missed an opportunity to screw with his baby brothers' afterlife, he took it to the kitchen.
Okay... so he'd admit that maybe vampires didn't remember absolutely everything. That little episode in the kitchen... it wasn't quite as video-vision as he's like it to be.
He'd dropped the glass, done it on purpose to catch it again... and she'd laughed... just like Katherine. And he stood there, looking at her and talking about Katherine and putting dishes in the dish washer. He couldn't remember a word they'd said. He'd been half heartedly trying to screw with her and Stefan in some way... but most of him had been slipping out of 'vengeful Damon' mode and into 'Damon and Katherine'... Because she looked like Katherine, and she sounded like Katherine, and -sweet torture- she laughed exactly like Katherine. And they were putting away dishes. Maybe he and Katherine would have put away dishes. He let himself pretend. He pretended for a few blissful minutes that she was Katherine...
And then she did something. She said something. Something so not-Katherine that he had to see her – Elena.
She told him she was sorry about Katherine.
And she genuinely was. Stefan's girlfriend was genuinely sorry for his dickhead older brother, who had stolen his first love and then lost her in a tragic fire. She was sorry.
Katherine wasn't sorry. Katherine was never sorry. She wasn't sorry for wanting the two-in-one Salvatore deal. She wasn't sorry for her get-what-I-want-and-screw-everyone-else attitude. She wasn't sorry for killing. She wasn't sorry for lying.
And Katherine never would have put away dishes. She would have had servants to do that for her. If she had been in this kitchen with him, they would have been screwing on the counter – maybe with a plaything or two watching.
And though he loved that. He still loved Katherine. And he played 'no rules' even without her...
Elena was sorry – for him.
He never managed to pretend she was Katherine again.
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