Day One of Twenty-Two Thousand, Give or Take

After a twisted plan left the life of his girlfriend Elena linked to that of his best friend Bonnie, Damon is forced to navigate his new reality without the love of his life. A newly empowered Bonnie has decided that she will be Damon's moral compass and keeps a close eye on him as he, in turn, cautiously keeps tabs on Alaric, following the loss of his fiancée Jo. Meanwhile, as he waits for Caroline to sort out her emotions, Stefan takes an active role in protecting the town from Lily and her family of Heretics, who have wasted no time wreaking havoc in Mystic Falls. Elsewhere, Enzo struggles to find his place in Lily's new life, and is quickly forced to decide where his true loyalties lie. Finally, with the stakes higher than ever, Matt, who has recently completed his deputy training program, teams up with Stefan and Caroline to put a stop to the Heretics, but an unexpected turn of events leaves one of them in a dangerous position.