Elena and Stefan are in bed and are rudely disturbed by Damon who is eager to start working on getting Katherine out of the tomb
At Elena's house Damon starts to flirt with Jenna. She reveals some past relationships with Damon. Elena goes to Aunt Jenna who thinks Damon is hot but lena disagrees. Damon and Jeremy play videogames. Elena and Damon cross paths while taking the plate back to the kitchen. Damon confronts Elena on if he can trust Stefan and Elena tells him he can.Jeremy told Stefan, Damon and Elena that Alaric had his ancestor's journal. This led to a confrontation between Stefan and Alaric. Alaric tries to shoot Stefan with a wooden stake! But Stefan caught it and finds out what Alaric really wants.
He witnessed Damon kill his wife, but her body was never discovered. Stefan says he can protect Alaric, but he needs that journal. When they turn to look for it, though, the journal is gone. Alaric made photocopies of it and hands them over.
As Elena and Stefan looks over this copied journal, they realize that Emily's spellbook - the grimoire - is buried with Stefan's father. They go to dig it up.
Meanwhile, Damon finds out that Jeremy told Anna about the journal. When Damon takes Jeremy to meet Anna at the Grill, and watches from afar, he recognizes her: she's the daughter of a woman (Pearl) he knew in 1864! Pearl was a vampire and was Katherine's friend. Damon follows Anna back to her hotel room and confronts her. She's been here for awhile, it turns out, and likes to have "others do her dirty work." She turned Logan. She shows Damon the journal she stole from Alaric because they both wish to open that tomb. Damon knows where the Grimoire is hidden.
Flashback the year is 1864. Damon ran away from the Confederate Army. His dad was disappointed in him, but confided in both he and Stefan that the town was getting together to round up the vampires and burn them in a church.
Damon made Stefan promise he wouldn't tell his father about Katherine, who both brothers seemed to know was a vampire and seemed to be sleeping with. Stefan agreed, but later asked his dad general questions about whether or not all vampires were evil. This arouses suspision and he makes sure Stefan is kept safe.
Pearl and Jonathan Gilbert begin to get close. Anna is in the frame. Emily comes up with a spells made it possible for Katherine and Pearl to walk in the sunlight. Katherine has some personal time with Stefan getting intimate and goes to bite him... but his father secretly slipped him vervaine and Katherine is captured. Damon blames Stefan for the incident because he had put his faith in his brother. Stefan apologizes but it falls on deaf ears. Pearl arranges Anna to help Katherine escape. Jonathan Gilbert is with Pearl and his compass goes crazy leading him to call his men to capture Pearl. Anna witnesses this, but is told by Emily that she has a plan to protect them. While Stafan saw Emily from a distance.
Back on the present day...
Ben is on a date with Bonnie, who kisses him. But her witch sense goes off and she knows he's a vampire. She makes an excuse to go to the powder her nose and tries to quietly leave, but Ben grabs her.
Damon finds Stefan and Elena with the grimoire. He tells Elena he was felt his trust break with Elena. He grabs Elena and feeds her his blood. He demands Stefan hand over the grimoire but Stefan tells him no so he threatens Stefan to give the grimoire over or else he turns Elena into a vampire. Stefan reluctantly hands it over in exchange for Elena. Damon is left holding the book.
Elena and Stefan are at the Gilberts, when the latter goes downstairs to get aspirin and learns that someone named Anna is there with Jeremy, just in the bathroom. Stefan makes the connection to the Anna he remembers from 1864 and runs upstairs to check on Elena. The window is open. She's gone.