A Date With Destiny

 is the third episode of the seventh season of The Vampire Diaries and the one hundred and thirty-sixth episode of the series.

Summary
DATE EXPECTATIONS – When Andrew asks Caroline out on a date, she becomes weary of his intentions. Evert decides to help her uncover the truth. Bonnie and Damon, on the other hand, are in danger after an impulsive decision. Stefan has his hands full with a revelation about his past. Meanwhile, trying to find out more about where she is, Elena discovers more than she has bargained for.

Main Cast

 * Nina Dobrev as Elena Gilbert
 * Paul Wesley as Stefan Salvatore
 * Ian Somerhalder as Damon Salvatore
 * Kat Graham as Bonnie Bennett
 * Candice Accola as Caroline Forbes
 * Zach Roerig as Matt Donovan
 * Matt Davis as Alaric Saltzman (credit only)
 * Michael Malarkey as Lorenzo

Special Guest Starring

 * Annie Wersching as Lillian Salvatore

Recurring Cast

 * Justice Leak as Malcolm (corpse)
 * Elizabeth Blackmore as Valerie
 * Jaiden Kaine as Beau
 * Scarlett Byrne as Nora
 * Teressa Liane as Mary-Louise
 * Luke Benward as William Duncan
 * Adam Gregory as Ethan Crane
 * Hunter Parrish as Andrew Montez
 * Alexandra Chando as Marge
 * Madison Riley as Cleo Mitchell

Guest Cast

 * Todd Lasance as Julian (flashbacks)

Trivia

 * Elena, Andrew and Marge are revealed to be Guardians.
 * Ethan voluntarily helps Caroline figure out what Andrew is up to.
 * It is revealed that Valerie was the first love of Stefan. She seemed afraid from Julian, who was in a relationship with Lily.
 * After discovering Malcolm's body, Lily and the Heretics retaliate by capturing Stefan and cloaking Elena's coffin.
 * Bonnie and Damon rescue Stefan from his captivity by Lily and the Heretics.

Continuity

 * This is the first flashback episode of Season Seven. The flashbacks take place in 1863.

Cultural References

 * A "date with destiny" refers to an inevitable future event or encounter, especially one which is likely to be momentous.