"When we met Damon in Season 1, we got those glimpses, tiny moments that suggested that he wasn’t all bad-boy vampire despite his dastardly swagger. In the pilot, he was lurking around Elena (the fog and crow as she’s in the cemetery) and his “dead ringer for Katherine” comment to Stefan in the “Hello, brother” scene suggested then that he’d seen her close up. And now we’ve seen that first moment. Personally, I didn’t find the flashback behavior to be out of character for Season 1 Damon: he’s lying in wait for a victim; he’s Katherine-obsessed and full of romantic ideas of passion, adventure, and danger; and he wants to keep his presence in Mystic Falls a secret — no doubt he knew that Stefan was also in town. This flashback scene also gives us more of a backstory for that strange moment of tenderness in Friday Night Bites: when Damon watches Elena sleeping and touches her cheek. He wasn’t only seeing Katherine in Elena, or his brother’s sassy and sympathetic new girlfriend, but a girl he’d shared his own moment with. Damon knew he had chemistry with Elena before they officially met."