|“||You know, I first met Isobel when I was a teenager. I fell in love with her instantly, although I'm pretty sure she never loved me. She was special. Part of why I hate vampires so much is because of what she became. How it ruined her. And I never would've sent her to Damon had I known she wanted to turn. It's my fault. I'm telling you this because I hoped maybe you'd understand.||”|
When they were in high school, John and Isobel dated and slept together. This relationship resulted in a child, Elena, who was delivered by John's brother, Grayson Gilbert. No one knew who the real father was at the time.
At some point, John told Isobel about vampires, which became something that she started to obsess over. He also gave her his Gilbert ring, because he wanted to protect her from the supernatural.
Finally, in 2007, Isobel expressed a desire to meet a vampire, and he sent her to Damon Salvatore. He did not know of her true motives, and later confessed to Katherine (believing her to be Elena) that had he known that she wanted to turn, he would never have sent her to Damon in the first place. John also admitted that part of the reason why he hates vampires is because of how becoming a vampire changed Isobel.
Throughout The Vampire Diaries Series
In season 1, it was revealed that Isobel and John met when they were teenagers. While John fell in love with Isobel, she never felt the same about him in return. However, she was interested in John's knowledge about supernatural creatures, and therefore she stayed with him. They soon began a sexual relationship, which eventually led to Isobel getting pregnant with John's child. She gave birth to their daughter and thanks to John, Isobel was able to deliver the baby in the hands of Grayson Gilbert, John's brother and a doctor who was unaware that John was the father. According to John himself, he was with Isobel during the delivery, and he later told Elena how heart-broken she had been while giving birth. Isobel decided to give up the baby because she and John were simply too young to take care of it themselves. Grayson and his wife, Miranda, who had been unsuccessful at having a child of their own, decided to adopt the child after Isobel ran off, and ultimately became Elena's adoptive parents.
John and Isobel's relationship didn't continue after the birth of their daughter Elena, and they instead went different ways and chose different lifestyles. While Isobel started studying supernatural creatures at Duke University, John had a very disdainful attitude towards vampires. This attitude only intensified after Isobel herself became a vampire in 2007, because he hated how much being a vampire had changed her from the woman he once loved. Once Isobel turned, the only thing she and John had in common was the desire to keep Elena protected from the supernatural world, especially where Stefan and Damon Salvatore were concerned.
While Isobel was married to Alaric Saltzman prior to being turned, she never told him about her past with Elena or John.
When Isobel died in Know Thy Enemy, it was never revealed how John handled it, although it could be assumed that he didn't really care; it was likely that the Isobel he knew so well in his teens was too different from the vampire Isobel that she had become for him to still have strong feelings for her.
Isobel: "Don`t screw this up. You know what you have to do, John."
John: "I got it. I won`t fail."
Isobel: "You better not. Katherine wants all of those tomb vampires dead, and I want to add two more to that list."
John: "Let me guess."
Isobel: "Stefan and Damon. I don`t want this life for her ."
John: "That was always part of the plan. Consider them gone."
Isobel: "She`s our daughter, John. We owe that to her."
John: "I know."
Season 1, Episode 21 - Isobel
- They share a mutual hate for the Salvatore brothers, Damon and Stefan.
- They were working for Katherine Pierce.
- Isobel, however, was much closer to Katherine than John.
- They met when they were teenagers and had their daughter.
- John was present with Isobel during Elena's birth.
- Isobel referred to John as "a teenage waste of space," implying she did not love him at all despite having a child with him.
- John brought Isobel to his brother Grayson when they learned she was pregnant.
- John was the one who sent her to Damon, making him indirectly responsible for her transformation.
- As a result, he did not approve of her new vampirism and felt regret for causing it.
- John loved Isobel deeply, referring to her as the "first girl I ever loved."
- Both were introduced in season one, and both died in season two.