|“||I'm so sorry, Elena. I was such a disappointment to you.||”|
Elena's relationship with her mother was a complicated one. Isobel became pregnant with her daughter at the tender age of sixteen and gave her up before leaving her baby's life. Seventeen years later, Elena learns that she was adopted and began searching for her mother. Their first encounter was in Isobel, a meeting that did not end well as Elena realized that Isobel was not much of a mother.
In Season Two, Isobel returns to see her daughter, but Elena is firm in not wanting to see her. Later on, Isobel kidnaps her and takes her to the cemetery where she points out a tombstone that was placed there by her parents. Isobel then commits suicide as Elena, crying, watches, ending their relationship.
Elena was born on June 22, 1992 to John Gilbert and Isobel Flemming. Isobel desperately wanted to keep her baby, but because she was a teenager, she was forced to give her child to John's brother Grayson and his wife Miranda. Since that day, Isobel dreamed of finally meeting her daughter and telling her who she really was, while her baby girl---named Elena--- grew up with the Gilberts.
Throughout The Vampire Diaries Series
In A Few Good Men, Elena finds out her mother's name and goes to see Isobel's high school best friend, Trudie Peterson. After Elena leaves, she is confronted by one of Isobel's minions, who tells her that Isobel has no interest in seeing her before he commits suicide. Elena then dials her mother's number on his phone. She hears Isobel for the first time, but Isobel hangs up the moment she hears Elena's voice.
In Isobel, Elena finally meets her mother but she is not who she wanted her to be. Isobel is more interested in taking the Gilbert Device than she is bonding with her daughter. Elena gives her the device, thanking her for being a disappointment as it keeps the memory of her real mother perfectly intact. Elena later cries after their encounter.
In The House Guest, Elena reunites with her mother once again, after she makes an unexpected arrival to the Gilbert home.
In Know Thy Enemy, Isobel kidnaps Elena. She was compelled by Klaus to keep her safe until the ritual to break Klaus's Hybrid Curse. She takes Elena to a cemetery where Isobel's parents placed a grave for her. She gets a phone call from Klaus's warlock Maddox. He tells her Klaus has everything he needs for now and that she is no longer needed. Isobel tells Elena how sorry she is for never being there for her, and for being such a disappointment to her daughter. As Isobel rips off her daylight necklace and screams in pain, Elena cries as she watches her mother being burnt alive. Elena later takes Isobel's necklace for herself.
- Isobel was 16 when she had Elena.
- Isobel was the first character to make Elena aware of Damon's love for her.
- Isobel gave birth to Elena in the Gilbert House, the home in which her daughter would live for most of her life.
- Elena hears her mother's voice for the first time in A Few Good Men.
- They are the first mother/daughter pair known to have been separated since birth in the TVD/TO universe, the others being Katherine and Nadia, Hayley and Hope, and Esther and Freya.
- They are both descendants of Katherine Pierce.
- They have both been vampires.
- Elena was cured and became human again while Isobel died a vampire.
- Both have slept with Damon Salvatore.
- Elena is most likely unaware of this though.
- Between her birth parents, Elena lost her mother first.
- She also witnessed her mother's death as opposed to her father's.
- Both have been turned by using Damon Salvatore's blood. Unlike her mother, however, Elena never wanted to be a vampire and Elena died with his blood in her system.
- They are the first mother/daughter pair to be introduced as frenemies/enemies.
- Elena cried when Isobel died.
- Their deaths have both been caused by Klaus.
- Isobel was compelled to commit suicide by burning in the sun.
- Elena was drained of her blood during the ritual to break Klaus' curse.
- Both mother and daughter have been drained of their blood, Isobel by Damon and Elena by Klaus.