Plot
Enzo probeert te vechten tegen de controle die er over hem is, Bonnie zit midden in een gevaarlijk spel en is gedwongen een hartverscheurende beslissing te maken tussen de twee belangrijkste personen in haar leven. In de Armory doet Alaric onderzoek naar een mysterieus object waarvan hij hoop dat hij hiermee de controle over Damon en Enzo kan stoppen. De neerwaartse spiraal waar Damon zich in bevind leid hem naar Tyler, die probeert hem tot rede te praten voordat het te laat is.

Gastrollen
Michael Trevino als Tyler Lockwood
Nathalie Kelley als Sybil
Allison Scagliotti als Georgie
Marguerite MacIntyre als Liz Forbes (“flashback”)
Lily Rose Mumford als Josie
Tierney Mumford als Lizzie
Nina Dobrev als Elena Gilbert (archive footage)
Jason MacDonald als Grayson Gilbert (archive footage)
Erin Beute als Miranda Gilbert (archive footage)
Weetjes

– Officiëlle uitzenddatum (USA): 4 november 2016
– Officiëlle uitzenddatum (NL): –
– Elizabeth Forbes is deze aflevering te zien in flashbacks
– Zach Roerig is niet te zien in deze aflevering.
– Dit is de 90ste aflevering waarin Alaric in te zien is.
– “You decided that I was worth saving” is de zin die Damon tegen Elena zei in aflevering 1×22.

Muziek
“Things Are Looking Up” – Billie Holiday
“Death Of A Bachelor” – Panic At The Disco
“Missile” – Dorothy
“Hey Joe” – Charlotte Gainsbourg

Links
Afleveringsstills
Screencaptures
Webclips/Previews

Quotes
Bonnie: (to Caroline) “Planning a June Wedding.”
Caroline: “Yes! The June Wedding!”

Damon: “Looks like litter brother is getting married. Consider this my R.S.V.P.”

Sybil: “Do me a favor and kill Bonnie Bennett.”
Damon: “Neck Snap… Heart Rip… Or just good ol’ fashion tear your throat out.”

Caroline: “Do you think we can get away with not inviting Damon to the wedding?”
Bonnie: “He’s going to be your brother-in-law.”
Caroline: “Fine. He’s not sitting at the head table.”

Georgie: “There’s nothing in the historical records about a weapon like this.”
Alaric Saltzman: “Please tell me there’s a but…”
Georgie: “But I have a theory, Okay… so… assuming that the symbol etched into it has a connection to hell, what’s the first thing you think of when you think of hell?”
Georgie: “The Devil, right, and what’s the most common visual representation of the Devil?”
Alaric Saltzman: “Ah… ah, a man in a red suit. Pointy tail… with a… pitchfork.”
Georgie: “Ding. Ding. Ding. Okay, in the medieval tradition the pitchfork symbolized the separation of the wheat from chaff which is obviously a metaphor for good souls going to Heaven and garbage souls going to the big fiery basement.”
Alaric Saltzman: “Well shouldn’t that have three tines?”
Georgie: “Not in 22 hundred B.C. when it was foraged. The soil around the Mediterranean was rocky so their pitchforks only had two.”
Alaric Saltzman: “Okay well that’s all very interesting but that doesn’t tell us anything about its connection to the Sirens, how we’d use it.”
Georgie: “We? Why would we use it? Like this is real as in some sort of magical weapon?”
Alaric Saltzman: “Come on you know what I mean.”
Georgie: “No actually I don’t. Sure this is for a book ‘cause your treating it like lives are at stake.”
Alaric Saltzman: “Worse… tenure. Okay, now keep digging.”

Stefan: “Look it this is all some sort of elaborate trap we might as well as skip to the part where you spring it.”
Damon: “No Trap, elaborate or otherwise, I just need your help”
Stefan: “With what?”
Damon: “I can’t tell you. No I mean I literally can’t tell you. I can’t physically make myself form the words. This thing about Sybil, she’s not big on free will. She kinda low-jacked my brain. Whenever I try and form the words to tell ya what’s going on it just comes out applesauce penguin.”
Stefan: “Well if you can’t tell me how to save you then I’m at a lost ‘cause I’m running out of ways to pull you back from the brink.”
Damon: “Sounds suspiciously like someone’s given up.”
Stefan: “Not yet but I’m not about to let Elena wake up to find out that you murdered her best friend.”
Damon: “This isn’t for Bonnie.”
Stefan: “Then who’s it for?”

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