Anna may look like nothing more than a fifteen-year-old girl, but she's wise beyond her years. She's over five hundred years old, has lived far longer than most vampires should, stayed in the long-term company of the infamous Katerina Petrova and even had a clever means of keeping the Originals at bay. Not only did she know Damon when he was human, innocent, and untouched by any of the horrors of the world they live in now, but she's seen people like him before. The ones that just, for some reason, get terrible after they're changed.

It's an unfortunate story each and every time.

"What do you want me to do, thank you for telling a boy who liked me that I died?" A boy she liked in return and still likes, but Anna's lived too long to get hung up on one boy whose life she was ultimately inferring in. She's not Katherine. "A boy whose neck you later snapped in the heat of a drunken hissy fit? Yeah, I saw that. I saw a lot of things while I was stuck on the Other Side, Damon."