The relationship between Pearl and Anna was that of a close mother-daughter relationship, even though they had their ups and downs. Pearl loved her daughter and didn't want to see her get hurt by Jeremy Gilbert, like she was by his ancestor Johnathan Gilbert.
Not much is known about Pearl and Anna's history as vampires except that Pearl was about 500 years old. If Anna was biologically Pearl's daughter, then she would be around this age too, take away a few years.
Sometime over the centuries, Pearl became best-friends with Katherine Pierce. Katherine, Pearl and Anna moved to a small town in Virginia called Mystic Falls. Katherine turned several inhabitants into vampires there, and the Founding Families started to suspect vampires were responsible. Honoria Fell asked Pearl to sell an elixir at a reduced rate, but Pearl discovered it had vervain. Pearl and Anna went to Katherine in hopes she would decided they should leave, but Katherine refused.
Anna helped her mother in an apothecary and saw how much her mother liked Johnathan Gilbert, a local scientist who was trying to create a device that would locate vampires. With the unknown help of Katherine's handmaiden Emily Bennett, a witch, the device worked and the townspeople caught 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 and taken away to Fell's Church be destroyed.
Emily told Anna the truth that she had found a way to protect the vampires in the tomb and Anna worked for the next century and a half trying to find a way to free her mother. Over the years, Anna ran into Katherine who had escaped before the vampires' "destruction". Anna knew that she had turned Stefan and Damon Salvatore, and that Katherine did not care for Damon, who too was trying to free Katherine from the tomb, not knowing she wasn't there.
In 2009, Anna met Jeremy Gilbert, a descendant of Johnathan Gilbert. She forged a friendship with him in order to get his ancestor's journals, which had information to free Pearl. Jeremy gave the journals to his history teacher Alaric Saltzman, so Anna stole it from him. Alaric had made a copy of the notes, but those were stolen by Stefan Salvatore. Reading the journal, Anna remembered how Johnathan and Pearl were in love with each other.
Anna tried to work with Damon, but lost the Bennett witch, Bonnie, after Stefan went to her motel to rescue Katherine's doppelgänger Elena Gilbert, Jeremy's sister. Bonnie and her grandmother Sheila Bennett agreed to open the tomb and Anna took her chance to get her. Anna told Jeremy she and Pearl were leaving, but decided to stay, enrolling Anna in Mystic Falls High School. She was devastated when she discovered that Pearl had been killed by John Gilbert.
In Ghost World, Anna only took Elena's necklace to see if she could find Pearl. Later on when Anna is walking down the street she sees her mother, Pearl, and they embrace, disappearing together finding peace.
In Stefan's Diaries: Origins, Pearl and her daughter Anna work in the Mystic Falls apothecary. Stefan stated that they could pass as sisters as it was a debate by young girls what Pearl's age could be. One night, Stefan saw Katherine leading Anna away in the forest and followed, thinking that Anna was Katherine's victims. He discovered that Katherine turned Anna at Pearl's request after her family died of a deadly disease. After Anna and turned, Katherine turned Pearl too. The cover story for them is 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 by the story-line of the T.V. series, Anna escaped that fate.
- They were both killed by John Gilbert.