Anna brings a surprising guest along when she pays a visit to Damon. Elena and Stefan go on an awkward double date with Caroline and Matt, but Stefan and Matt find they have some common ground. Jenna reunites with her old friend Kelly, and Jeremy's relationship with Anna takes an unexpected direction.

While Stefan struggles to control his new situation, Elena and Jeremy are surprised by a visit from their uncle, John Gilbert. Alaric has an awkward talk with Elena about Isobel. At a Founder's Day event, Stefan displays a rare party attitude and Damon's attempt to find out why Uncle John has returned to town takes an ugly turn. An incident at the party causes trouble between Matt and Tyler, and the relationship between Matt and his mother, Kelly, reaches a new low. Meanwhile, Elena's effort to comfort Jeremy falls short and he decides to take matters into his own hands.