Anna (Malese Jow) brings a surprising guest along when she pays a visit to Damon (Ian Somerhalder). Elena (Nina Dobrev) and Stefan (Paul Wesley) go on an awkward double date with Caroline (Candice Accola) and Matt (Zach Roerig), but Stefan and Matt find they have some common ground. Jenna (Sara Canning) reunites with her old friend Kelly (guest star Melinda Clarke), and Jeremy's (Steven R. McQueen) relationship with Anna takes an unexpected direction.