Emiya
Damn it, the former Servant thought as she looked up at him with those teary, mismatched eyes.
His broad shoulders slumped as he sighed and shook his head. "Yare yare, making a man bringing up some of his biggest mistakes," he said with a half-smile to take the edge off of his sardonic words.
"So, there was this idiot named Emiya Shirou, and he had the brilliant idea that he wanted to be a Hero of Justice . . ." he began as he told her all he remembered when he had been that teenage boy all of those years ago.
He told her about Saber and the complicated feelings there, about how he failed her and how the vision of her was forever burned into his mind, even after he'd seen the depths of his own Special Hell. About, "That asshole Lancer who stabbed me in the heart because he's a drunken, Irish asshole," Gilgamesh, Tohsaka Rin and more complicated feelings, the Tragedy of Ilya and how her death haunted him to even this day, and to Sakura, the girl who had been his dearest friend in the end, and how he failed even her.
Then he told her what happened after the War, his Faustian pact with Humanity to be it's literal bitch, and iterations of him being summoned to different places, and how, until Chaldea, Tohsaka Rin was the only person who gave him any respite from being a Counter Guardian.
His tone and description when he was telling her as his tenure as a Servant was different than him telling her about being a master. It felt more academic as he was going from records he had access too and lacked emotion at points, as if he was an outsider reading someone's detailed diary.
He told her about all of his retroactive suicide plans. How he had succeeded. How most of the time he ended up dying to save Rin. He even told her how he stood there like a goddamn potato every time he saw Saber for the "first" time again.