Caroline sees him at the bar in the Grill one day. He's alone and nursing a glass of whiskey and she's alone and wishes she could have some whiskey.
"Why did you choose me?" she asks as she slides up next to him.
He spares her only a cursory glance before staring back at his glass. "I believe," he says slowly, as if speaking to a small child, "it was you who came up to me just now."
Caroline sighs and wonders if he's being deliberately obtuse or if he honestly doesn't know to what she's referring. "It doesn't matter," she mumbles to herself. She asks the bartender for a soda and smiles sweetly when Damon compels the guy into adding a little something to make it taste better.
Sometimes it amazes her how he has this uncanny ability to know exactly what she wants.
She sips her drink slowly, savoring the taste, as she watches him watch the ice cubes in his own glass melt. Finally, she's had enough. "You know what, Damon?" she asks shrilly, not really wanting an answer. "I've changed my mind. It does matter. It matters to me. I deserve to know why you let me take you home that night—" her voice drops to a whisper "—and I deserve to know why you compelled me, why you fed off me, why you played with me like you did for months! There has to be a reason, and I deserve to know it."
She wonders why she's choosing now—when Tyler's MIA, when Matt has just recently discovered her secret, when she's fighting for her life and for the lives of half of Mystic Falls—to ask the question that has been on her mind since she's turned. And, from the look on his face, she suspects he's wondering much the same thing.
His face goes blank again, and he downs the rest of his glass before answering. "At first it was convenience—you were a wealth of knowledge on Elena and this town, you were close to Elena and my being with you therefore irritated her, and the sex was great. Then you were necessary—because, really, who else stood a chance at getting that necklace away from that little witch. And then…and then, I don't really know."
She nods and accepts the answer because she knows he's telling the truth.
"Don't take that to mean I cared about you in any way, shape, or form," he warns when his glass is refilled.
She nods once more and doesn't speak again, but another question is now begging to be asked.
Why did he rush to the hospital when she was in that car accident, and why did he offer to give her blood?