As Alaric and Jo reluctantly participate in their bachelor and bachelorette parties, Damon and Elena discuss the ramifications from an impulsive offer that Damon makes. Unsure of what to do, Elena turns to Bonnie and Jo for advice, but is left conflicted when Bonnie raises some unanticipated concerns. When Enzo realizes Lily is on a dangerous downward spiral, he asks Stefan to help intervene before it's too late. Lastly, fed up with the supernatural threats that plague their town, Matt takes his frustrations out on Tyler, while Alaric considers a life-changing piece of advice.

In the aftermath of Alaric and Jo's powerful nuptials, things take a dramatic turn when an uninvited guest shows up, leaving Elena in terrible jeopardy. Despite Matt's advice to leave town to protect herself, a defiant Bonnie takes matters into her own hands after finding herself on the receiving end of a twisted plan. As Stefan and Caroline reach an emotional crossroad in their relationship, a reunion with Liv leaves Tyler faced with a decision that could change his life forever. Meanwhile, Lily's reckless actions cause Stefan to realize the lengths to which his mother will go to reunite with her "family." Finally, after a devastating chain of events, Damon is forced to make the most difficult decision of his life.