- "Well frankly, I don't care about what he did to you, to Katherine, to anyone. He deserves none of what you are doing to him, and this woman, she didn't deserve this either. We are your only family but we're split up, and this is why. You're selfish, and you have to let the deal with Katherine go. She's gone Damon. Gone. And now we lost Stefan too... to God knows what. Goodbye, Damon."
- —Roxie to Damon about Stefan.
After the witch's death Roxie went on her own for over a few decades, spending most of her time in New York where she went by a new name every decade and went to different schools where she learnt a lot and made friends before disappearing again so that no one would notice she didn't age. She became a master of disguise and alternative identities.
She didn't go back to Mystic Falls until in 1912 to attend the funeral of their late nephew Zach where she met Damon and Stefan for the first time in what seemed like forever but the reunion of the siblings ended badly when Damon made Stefan drink blood from a girl that he accidentally ended up killing. Roxie ran off to Europe, motels or camped in the forests for a while and then she again began to compel herself great hotel-rooms and luxury for her own good. She explored the world and went to many places, unfortunately alone. One day a werewolf pack crashed her camp in a forest outside Cleveland that she had set up after months of living at a fantastic hotel in Greece. She ran away, and without even realizing where she was heading, the little vampire ended up in the 21st Century’s Mystic Falls, more specifically 2009, only a few months later than her brothers.
In 1912 she returned to Mystic Falls for the funeral of her late nephew Zachariah and sees her brothers for the first time since they parted in 1864. She joins her brothers for a drink and goes with them to a boxing match and everything seems to be going fine when the siblings' reunion suddenly reaches a turning point. Damon persuades a very resistant Stefan to have a drink of human blood with him again, selecting Marianna Lockwood and luring her away from the crowd with the trio, Roxie desperately telling Damon to stop. Stefan gives in and feeds but quickly loses control of himself and accidentally rips her head off, leaving Roxie speechless. Stefan becomes angry with Damon for forcing him to drink human blood and runs off into the woods. Damon and Roxanne watches him go, and then have an argument about their brother's well-being. Enraged, Roxie runs off to Europe, moving from country to country and taking up different names each time just like before.