|“||Now that I have your attention, listen up. You do not come into my town, threaten the people I care about. Going after Elena? Bad move. You leave her alone or I will rip you to bits because I do believe in killing the messenger. You know why? Because it sends a message. Katherine wants something from me? You tell that little bitch to get it herself.||”|
The relationship between the cured vampire Damon Salvatore and the vampire Isobel Flemming was a sexual relationship. Damon turned Isobel into a vampire, and Isobel then came back to Mystic Falls, and threatened the girl he was in love with, who also happened to be her daughter, Elena Gilbert.
Presumably in the early 2000s, Isobel became obsessed with a little town not far from where she and her husband lived. The town, Mystic Falls had a history of animal attacks roaming the town and often killing their victims. However, when she researched more in to it, she came to the conclusion that it was vampires responsible for the attacks, an assumption that was proven correct in later years. She then became obsessed with becoming one, and called up her old flame, who just so happened to know one, Damon. John sent Isobel to him, unaware that she wanted to turn, in which according to Damon she "begged" him to turn her, in which he did, after biting her and feeding on her blood. At some point in the time they knew each other, they began a sexual relationship, which at the time was when Isobel was still together with her husband Alaric Saltzman.
Throughout The Vampire Diaries SeriesIsobel and Damon didn't see each other again until 2009. Her husband Alaric moved to Mystic Falls to teach as an history teacher at the local school, and also to find Damon as he had information about Isobel he wanted to know. After a couple of months of events, including Damon killing Alaric, and coming back to life because of a ring Isobel gave to him, and Damon finally finding out that Isobel is also Elena's birth mother, lead up to her reappearance in Mystic Falls. Isobel finally returns back to the town of Mystic Falls and comes face to face with the husband she abandoned and the daughter she gave up.
Once Damon found out Isobel had arrived in Mystic Falls. He checked every local bank and found the biggest for closure, in which was a Mansion a couple of minutes outside the town. However, when he arrived, it was empty except for one of Isobel's "minions", Cherie. The two played strip poker until Isobel arrived back. She told Cherie to leave and the two talked about the Gilbert Device which is harmful against vampires. They then started to make out, until Damon smashed her neck onto the floor, and threatened to kill her if she doesn't leave town and stop threatening the people he cared about. She eventually left town, after she got the device.
- They had a sexual relationship.
- Damon is in love with her daughter.
- Damon has slept with three members of the Petrova Family: Katherine, Isobel and Elena Gilbert.
- Damon killed and turned her into a vampire.
- Damon slept with both Elena and her mom, but that doesn't seem to bother Elena (if she knows).
- They were both antagonists on the show at some point during the series.
- Isobel recognizes Damon's love for Elena.