|Fifth||Turned: By Katherine Pierce in 1864|
Damon is first seen trying to stop Klaus from killing Rachel. He threatens to stake Klaus, to which Klaus says he has to stay away or he'll kill Rachel. Klaus then bites his wrist and shoves it into Rachel's mouth before Damon can do anything. Damon tells Klaus not to, but he snaps Rachel's neck. He rushes to her side, Klaus gone, and rests her on his shoulders.
Later we see Damon enter his apartment, laying Rachel on a red couch. After he does that, he drinks from a bag of blood. Upon hearing Rachel gasp, he asks her name. He claims that her name has 'Star Quality' to it. He then introduces himself. After a short conversation he tells Rachel that Klaus turned her into a vampire. Rachel starts panicking and he gets a bag of blood for her. She refuses to drink any blood whatsoever. Damon tells her that if she doesn't drink it, she'll be dead within the next twelve hours, after that, Rachel accepts and drinks it. A few minutes later, Rachel is puking up the blood. Damon says to her that she needs to drink blood from an actual human, not a bag.
In the busy NYC streets, Damon points out a tan, muscular man who looks around 21 years of age. He tells Rachel she is stronger than him now she is a vampire. Upon entering the alley, Damon nods at Rachel, signalling she can drink from the man, now known as Brad. After she has drank enough, Damon says that she has had enough. She doesn't stop, and the head falls off of Brad's body. She turns around, blood covering a portion of her face. She then asks Damon what she did.