When an impulsive decision by Damon threatens to unravel a carefully negotiated deal between Stefan and Lily, he has no choice but to make amends with his mother before things spiral further out of control. However, Lily remains one step ahead and carries out a harsh plan that hits Damon where it hurts most. Elsewhere, after returning to Whitmore College, Alaric turns to Bonnie for help with a mysterious and potentially dangerous artifact he has obtained, while Matt is forced into making a risky life or death decision. Meanwhile, Caroline, who finds herself a pawn in Lily and the heretics' plan for retribution, uncovers a shocking detail about Stefan's past.

Damon的冲动举动使得Stefan和Lily精心安排的协议面临崩溃，他不得不找到母亲来修补失误，以免事情失去控制。
但Lily早行一步，其严酷的计划要打击Damon最软弱的方面。
Alaric得到一个神秘的东西, 他回到Whitmore学院的寻求Bonnie帮助，而Matt则则必须做出一个有关生与死的决定。
Caroline发现自己成了Lily和异徒报复的工具，并因此发现了Stefan过去令人震惊的历史。