This week was a trip back to the past where we see Evil Elaina aka Katherine working her wiley vampiric ways on both Salvatore brothers. Nice! Katherine is staying with the Salvatore’s whom Emily works for; while she helps the vampires. We also learn that Pearl is Anna’s mother; and may be locked in the tomb with Katherine and the others.
Despite his sons dipping into the vampire honey pot, Pappa Salvatore, Mr. Gilbert (who is sweet on Pearl) and the other villagers are looking to eradicate them. Pappa S figured out the boys’ were sympathizers and laced their food with vervain. It's finally Stefan’s turn to tap Katherine, but when she goes in for the big finish, it's she who is done--vervain, nature's cock-block. Sadly, Mr. Gilbert also lost his love when, the same night they carted off Katherine, he realized it wasn’t just his man-parts pointing in Pearl’s direction, but the compass as well.
Meanwhile in the future, Elaina and Stefan are waking up together. Damon walks in and they freak out; to which Damon retorts, “If I see something I haven’t seen before, I’ll throw a dollar at it.”
Anna and Ben are plotting in their hotel; Ben for Bonnie and Anna for the journal. Anna turned Ben because he was “sad and lacked purpose”—apparently being a bartender fixed all that. On the Bonnie date Ben gathers intel and Bonnie calls Elaina to give her the scoop (loser). When she returns, she tries to suck Ben’s face off and realizes he is a vampire. Although she plays it cool, Ben doesn’t buy it; meeting her at the door and dragging her out.
The race for the journal is on. Luckily, the history teacher is at the school—because apparently it’s normal for him to be there at 10pm, reading a journal like a homeless person. Stefan gets there at the same time Anna does—she gets the journal (which Damon will snatch from her) and Stefan gets the teacher’s story about Damon killing his wife (allegedly) and a copy of the journal.
Damon is cooking dinner for Jenna who is getting drunk on wine. Damon gets very intense with Elaina asking if he can trust Stefan and that he’ll do anything to get Katherine back. Later, a drunken Jenna is telling Elaina that Damon is “ridiculously hot”—Ok, Jenna, try to keep it in your pants.
The journal leads Elaina and Stefan to Pappa Salvatore's grave, where they exhume Emily’s spell book out of Pop’s coffin—just at Damon shows up. Hurt and angry that they crossed him, Damon grabs Elaina and makes her drink his blood, threatening to snap her neck. Stefan traded the book for Elaina.
Back at Elaina’s Stefan goes downstairs to get her an aspirin and hears Jeremy has a friend over – Anna. Stefan suddenly remembers who she is, runs upstairs, but Elaina is gone.