THE DEVIL FROM CHRISTMAS PAST — Faced with the fallout from his interaction with Cade, Stefan is determined to have one thing go right – Christmas Eve with Caroline. However, when Damon and Sybil crash their Christmas Eve dinner, which had been joined by Alaric, Matt and Peter, things quickly take a dark and twisted turn. Meanwhile, in a series of flashbacks to Stefan's past, Cade's tempt to entice him with his mysterious agenda leaves Stefan faced with an unimaginable decision. Bonnie and Enzo also appear.
The flashback from Christmas 1917 In Monterey shows Stefan killing the entire village.
In the present, Stefan tries to make his last day of freedom as meaningful as possible. Caroline, Alaric and the twins arrive for the Christmas dinner. Sybil and Damon also come uninvited, so Alaric takes the twins home as a precaution.
Meanwhile, Enzo and Bonnie were planning a trip to Paris when Caroline phoned them to tell them not to come to dinner since Sybil is there. Caroline also plans on getting the location of the tuning fork by getting Sybil drunk. Sybil reveals that her house in at Pond Estates and Caroline passes this information to Bonnie and Enzo who go to search the house.
At the dinner, Damon stabs Stefan which transports him to another dimension with Cade. He shows him the consequences of his ripper massacre a century ago. He also reveals that Seline witnessed this night. Stefan proposes to Cade to serve him only one year but with his humanity turned off instead of eternity. Cade agrees but says that he believes that Stefan's gonna continue to serve him after that because he'll wants to.
Alaric tells bedtime stories to the twins, but they keep asking about Seline. Bonnie and Enzo arrive to Sybil's house, but only Bonnie is able to enter because Enzo's a vampire. She finds Seline there with the fork in her hands surrounded by a random family. Seline agrees to give them the fork if they help her remove her influence from the twins' minds. She believes that if she does something good, she won't end up in hell.
Meanwhile, Matt and his father Peter also arrive for the dinner. Damon announces that his Christmas gift this year will be killing someone in the house. He asks everyone about the worst thing they'd done as a way to determine who deserves to die the most. He questions Peter who reveals that he left Matt and Kelly for no reason. Later while Sybil is questioning Peter about the location of the Maxwell family heirloom, Bonnie and Enzo arrive and use to fork to weaken her. The fork also affects Bonnie this time. Sybil grabs Peter and escapes.
Elsewhere, Damon gives Sybil a gift he'd taken from under the tree. It turns out that it's Elena's necklace. Some memories return and he rips Sybil's heart out and leaves her to die.
Meanwhile, Alaric brings the twins to say goodbye to Seline. She takes away her magic from them and leaves.
Stefan enjoys the final few hours with Caroline and the twins. At midnight, he leaves the town with Damon and turn his humanity off.
- Antagonists: Stefan (flashback), Damon and Sybil.
- This is the eighth and last mid-season finale of the series. This is also the first mid-season finale to be on the seventh episode.
- For the first time, Damon and Stefan have their humanity off at the same time.
- Cade tells Stefan that until he met Elena she was headed on the right path but by Stefan meeting her made Elena into something dark. This indicates that Elena could end up in Hell. Cade tells Stefan that souls like Elena's who would just squeak by into Heaven are the ones he wants Stefan to go for.
- Cade accepts Stefan's deal that he and Damon will serve him for only 1 year and will not go to Hell.
- The Ripper of Monterey event in 1917 is revealed to happened at Christmas time and that Seline was a witness to it.
- Cade is the third person, after Klaus and Caroline, to make Stefan become the Ripper.
- Damon rips out Sybil's heart after seeing her wearing Elena's old vervain necklace, seeming to indicate he remembers Elena as the woman he loves.
- When Seline asks Tammy to sing her "something nice and easy" Tammy sings "O Holy Night" - the song that was playing in the first Christmas episode - O Come, All Ye Faithful.
- The song was playing when Klaus kills his hybrids.
- Inhabitants of Monterey - Blood loss; killed by Stefan (flashback)
- Stefan Salvatore - Stabbed with wooden ornament; killed by Damon (temporarily)
- Sybil - Heart extraction; killed by Damon (temporarily)
- Monterey (flashback)
- Mystic Falls, Virginia
- Grove Hill, Virginia
- This is the eighth mid-season finale to feature Stefan and Damon; the seventh to feature Bonnie, Caroline and Matt; the fifth to feature Alaric; the third to feature Enzo; the first to feature Cade, Sybil, Seline and Peter.
- This is the second mid-season finale not to feature Elena.
- This is the series' fourth and last Christmas episode.
- This is the second episode in which two vampires have their humanity off at the same time.
- This is the final episode to air in 2016.
- Penny was mentioned by Damon. She was last seen as a hallucination in Gods and Monsters.
- Georgie was mentioned. She was last seen in Coming Home Was a Mistake as a corpse.
- Sheila was mentioned. She was last seen in Home as a ghost.
Behind the Scenes
- "The Next Time I Hurt Somebody, It Could Be You" is a line from Stefan from season one's Blood Brothers.
- With its thirty-six letters (ten words), this episode has the second longest title in the series.
- The first is Detoured On Some Random Backwoods Path to Hell with thirty-nine letters (eight words).
- Hashtag during the airing is #DecktheHells