Jeni Perillo

Anna brings a surprising guest on a visit to Damon; Elena and Stefan go on an awkward double date with Caroline and Matt; Jenna reunites with her old friend Kelly; Jeremy's relationship with Anna takes an unexpected turn.

Matt is surprised by the return of his long-lost mother; Elena and Stefan worry about Damon's new attitude; Elena searches for information about her birth mother.

Rayna and Teddy are sobered to learn that they are facing financial ruin, but Rayna won't consider borrowing money from her father or going on tour with Juliette.