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— Anna in shock with being reunited with Pearl again in Ghost World
The mother-daughter relationship between the vampires Pearl and Anna was that of a close mother-daughter bond, although they did have their ups and downs over the span of their long lives. Pearl loved her daughter and didn't want to see her get hurt by Jeremy Gilbert in the way that she was hurt by his ancestor Johnathan Gilbert.
Not much is known about Pearl and Anna's history as vampires aside from the fact that they were both over 500 years old.
Sometime over their centuries of life, Pearl became best friends with Katherine Pierce. Katherine, Pearl and Anna moved to a small town in Virginia called Mystic Falls, where Katherine turned several inhabitants into vampires there, which ultimately led the Founding Families to start to suspect vampires were responsible. Shortly afterward, Honoria Fell brought a large quantity of an elixir to Pearl's apothecary shop and asked her to sell it at a reduced rate, but when Pearl opened the vials to determine its contents, she discovered it contained vervain, revealing that the Founding Families were becoming more suspicious. Pearl and Anna went to Katherine with this information in hopes she would decide that they should leave, but Katherine refused on account of her plans for the Salvatore brothers.
Anna helped her mother at her shop and saw for herself how much her mother liked Johnathan Gilbert, a local scientist who was trying to create a compass that would locate vampires. With the unknown help of Katherine's handmaiden Emily Bennett, a witch, the device worked and the townspeople used the enchanted compass to catch all the vampires in town, including Katherine. Pearl tried to find a way for herself and her daughter to escape, but was caught by a shocked Johnathan, who was holding the compass and who immediately realized that Pearl had been a vampire the whole time. Despite her pleas, Johnathan turned Pearl in to the rest of the members of the vampire round-up and she was taken away to Fell's Church be destroyed, separating her from Anna, who was hiding nearby with Emily.
Emily confessed to Anna that she had found a way to protect the vampires in the tomb and cast a spell that protected them from the fire that was set, but trapped them inside using the power of the comet that was flying overhead at the time. Because of the specific requirements for the spell to unseal the tomb, Anna ended up spending the next century and a half trying to find a way to free her mother from her prison. At some point in the 1980s, Anna was in Chicago and ran into Katherine, revealing to her that she was not trapped in the tomb with the rest of the vampires like everyone else believed and had managed to escape before their "destruction." Anna knew that she had turned Stefan and Damon Salvatore into vampires at some point before she was captured, and understood that Katherine did not care for Damon, who was also working on his own plan to free Katherine from the tomb, not knowing that she wasn't there as he was led to believe.
Throughout The Vampire Diaries Series
In 2009, Anna met Jeremy Gilbert, a descendant of Johnathan Gilbert, at the local library. She forged a friendship with him by bonding with him over their interest in vampires in order to get access to his ancestor's journals, which had information on how to free Pearl from the tomb. However, Jeremy had given the journals to his history teacher Alaric Saltzman, which forced Anna to steal it from him. Alaric had made a copy of the notes just to be safe, but those pages were stolen by Stefan Salvatore, which clued him into what his brother was planning. Reading the journal, Anna remembered that Johnathan and Pearl were in love with each other.
Anna captured Elena (Jeremy's sister and Katherine's doppelgänger) and Bonnie (a Bennett witch) in order to help motivate Bonnie to help her unseal the tomb, and also tried to work with Damon to expedite her plan. Unfortunately, Bonnie and Elena were rescued by Stefan when he found them at her motel room, so they no longer had a witch to break the spell. ent to her motel to rescue Katherine's doppelgänger Elena Gilbert, Jeremy's sister. Knowing that Damon would not relent until the tomb was opened, Bonnie and her grandmother Sheila Bennett reluctantly agreed to open the tomb, and Anna took the opportunity to sneak in to rescue her mother. Once in the tomb, Anna used Elena's blood to awaken her mother, who had desiccated during her 145 years without any blood to sustain her.
Afterward, Anna told Jeremy she and Pearl were leaving, but she ultimately decided to stay due to her feelings for Jeremy, against Pearl's better judgment; she even went so far as to enroll at Mystic Falls High School. In Blood Brothers, Pearl was staked to death by John Gilbert, and when Anna returned home to find her body, she was absolutely devastated.
In Ghost World, Anna took advantage of the accidental spell that allowed ghosts to be visible and have a corporeal form in the living world to fully reunite with Jeremy. At some point, she stole Elena's necklace (which was the talisman of Esther Mikaelson and the power source for the spell), but while it was assumed that she did it to stay with Jeremy, she confessed it was really because she was trying to find her mother. She anxiously informed Jeremy that she couldn't find her anywhere, and that she wasn't sure if she was on the Other Side. Fortunately, Anna and Pearl were able to reunite right before the spell was reversed, allowing them to embrace tightly before the two of them disappeared and finally found peace together.
In Stefan's Diaries: Origins, Pearl and her daughter Anna worked in the Mystic Falls apothecary. Stefan stated that they could pass for sisters, as it was often debated by young girls what Pearl's true age could be. One night, Stefan saw Katherine leading Anna away in the forest and followed them, thinking that Anna was one of Katherine's victims. He then discovered that Katherine had turned Anna at Pearl's request after her family died of a deadly disease. After Anna was turned, Katherine turned Pearl as well. The cover story for them was that Pearl's husband died in the war, and that she and her daughter moved to the town to start a new life.
When the vampires were being rounded up, Johnathan Gilbert discovered that Pearl was a vampire. She was taken away to be destroyed, and, judging by the story-line of the T.V. series, Anna escaped that fate.
- They were both killed by John Gilbert.
- They were both in love with a member of the Gilbert family (Jeremy Gilbert for Anna and Johnathan Gilbert for Pearl).
- Both Anna and Pearl found peace when they were reunited, and were the first supernatural spirits to be seen finding peace on screen after crossing over to the Other Side.