Anna is still older than him by a lot even after he had that eighty or so years in the universe of hell, which he will return to. Damon feels he was terrible before he was a vampire too. He was human, and he was weak and pathetic. He knew exactly what was going on with Katherine and kept it from his brother, because he was jealous of how everyone felt about Stefan and liked the idea that the woman he was in love with might love Damon more. He was petty, and he got what he deserved and what he chose even if he spent decades blaming Stefan for it.

Damon manages to flinch when she mentions that. It's true, of course. He did it. One of those things he immediately regretted, but it doesn't change what he did.

"No. I'm saying life sucks either way." There's a low release of breath. He is not the Damon in Mystic Falls. He is the Damon that went to Chicago, that spent decades in hell with no chance for an escape from it, from his guilt, from what he has done. It's one that grew to care about Jeremy in his own way. The admittance comes so quiet and low. "I would take it back."

Killing Jeremy, he would take that back if he could, but he can't. "Jeremy ended up in Chicago too. I don't know how things turned out back home, but he had an actual life there. He hunted things, graduated from high school, all those big milestones."