Ten years ago: Alaric and Dorian are at the scene of a massacre. Five people have been killed and fed on, and their bodies have been burned. A Salvatore School pin clutched in one of the victims’ hands points to a student being the killer.
Present: Lizzie’s upset with Alaric for telling her that Sebastian chose to leave the school when she now knows that he was sent to the prison world. Sebastian rats Emma out for assisting him. Alaric would like to delay this argument until they’re no longer in a world with a psychopath. Sebastian tells him that since they’re in a new world, Alaric isn’t automatically in charge. Alaric responds by staking him in the gut. He announces that he and the twins are leaving, Sebastian is staying behind, and Alaric is most definitely in charge.
He gathers weapons as Josie tries to calm him down – yes, they’re in Kai’s world, but he’s desiccated. Alaric says she doesn’t know what Kai is capable of. They can’t take any chances. Josie asks who could have set Kai free. Alaric says he’ll explain later. Right now, she needs to get the mora miserium, then hide in Vamp Villa. Josie feels responsible for what’s going on, since her use of black magic led to all this, but Alaric says everyone makes mistakes.
Lizzie asks Sebastian what made Alaric so angry with him. Sebastian says Alaric sent him there to keep him away from Lizzie. He’s happy to see her again but doesn’t think they should be there. She promises that when they find a way out of the prison world, they’ll take him with them. Sebastian clarifies that they shouldn’t be in Mystic Falls. There’s a big world out there, and they have it all to themselves. He wants her to come see it with him, at least for one day. Lizzie doesn’t want to disobey Alaric, but Sebastian says he lied – there’s no one else there.
Alaric goes to the bar where Bonnie left Kai. “Two Princes” is still playing on a continuous loop. Kai isn’t there, but there’s a note labeled “to whom it may concern.” When Alaric picks it up, a video starts playing on a nearby screen. It’s of Kai warbling “All By Myself.”
Josie returns to Vamp Villa with the mora miserium and finds Lizzie and Sebastian gone. In their place is a teenager Josie recognizes as Jade.
Ten years ago: Josie spies on Jade and two classmates, Wendy and Diego, who are in detention (which at the Salvatore School means being trapped by a barrier spell). Jade’s frustrated that she’s being kept from a party where she was going to see someone named Inez. Diego’s a werewolf, and he did something during his transformation that landed the three students in detention.
Jade spots Josie, who’s around seven at this time and still naïve enough to fall for Jade and Wendy’s manipulation when they talk her into siphoning the barrier spell. She just thinks she’s doing something nice for some cool big kids.
Present: Jade’s a vampire, and she’s thrilled to run into someone she can snack on. Before she can get close enough to drink Josie’s blood, she’s staked from behind. Kai, who once tried to kill Josie before she was even born, has just saved her life. “Come with me if you want to live,” he tells her.
He takes her to the old mill, which he’s made his home and named Fort Parker. He offers her a mini-bottle of vodka, though he’d prefer Zima. Each of them knows who the other is, though Kai doesn’t know which twin Josie is, “Linda” or “Joanie.” He basically brushes aside the fact that he killed her birth mother and almost killed her and Lizzie. She calls him a monster, but he says a monster would have let Jade kill her. Jade and her buddies are the real monsters. They run the prison world, and they revived him from his desiccation just so they could mess with him. They hunt him down and kill him every day. Since he’s magically bound to the world, he can’t die, so it just repeats over and over. “Welcome to the supernatural Hunger Games,” he says.
Josie asks why Jade is there, but Kai won’t answer any questions until she answers his. For starters, why is she there? She tells him about the mora miserium, and he complains that she sent it there without thinking about the danger it would put him in. Josie clarifies that they tried to make a new world, but Alyssa tricked them and landed them here instead. Kai notes that she’s talking like someone else is with her. Josie uses his own rule against him and says she won’t tell him anything else until he answers another of her questions. Again she asks why Jade is there. Kai says he’s not the one she should ask.
On the video at the bar, Kai wonders if he’s talking to Damon, Bonnie, or Katherine. He dedicates his performance to Alaric, who’s the reason he’s alive. He knows Alaric dumped students over there. As soon as they got bored, they woke Kai up. He wonders if Alaric himself is the one he’s talking to. Alaric wouldn’t be dumb enough to come to the prison world, would he?
Alaric fires his crossbow into the TV, ending the video. Someone attacks him from behind and he drops his weapon. It’s Diego, and he’s pretty ticked about being sent there all those years ago. Because he’s in a world where the same day repeats over and over, and there’s always a full moon at night, he’s evolved to be able to turn at will. Now he’s going to show Alaric what he can do. But as he’s facing off with Alaric and his crossbow, Kai zooms in and rips out Diego’s heart. Alaric responds by firing a crossbow bolt into Kai’s heart.
Josie comes in and tells Alaric that Kai saved her life. Alaric chastises her for being around him, but Josie’s more concerned with the fact that, according to Kai, Alaric sent some students there to punish them. He repeats that everyone makes mistakes. He doesn’t want to make the same one twice, so he’s going to kill Kai for good. Josie tells him that’s not possible in the prison world, but Alaric’s going to try anyway.
Sebastian takes Lizzie to a mansion and tells her it’s hers. He’s found a dress for her to wear so they can act like they’re royalty or something. I don’t know; their stuff in this episode is boring.
Kai wakes up unsurprised that Alaric killed him. He’ll give Alaric the first death for free, but after that… He doesn’t finish, since Alaric is unconscious. Josie has chained him to the chair where Bonnie left Kai years ago. She explains that she didn’t want Alaric to stop her from getting everyone out of the prison world. She’ll do anything to accomplish that, even team up with Kai.
They go to the clearing where the witches made the new ascendant. He tells her they need a celestial event, Bennett blood, and the ascendant from this world. He went looking for that as soon as the others woke him up. He won’t tell Josie if he found it, though. He guesses that she has Bennett blood, but since she didn’t get to pack for the trip in advance, she says she doesn’t. Kai asks what she’s contributing to their partnership, then. She won’t tell him until he clues her in to the celestial event they’ll use to leave. He doesn’t know of one, but he’ll figure it out. It’s not like he’s pressed for time.
Josie asks if the mora miserium contains enough magic to power the ascendant without a celestial event. Kai says it might. It’s somewhere in the clearing, but Josie put a spell on it to keep it hidden. He notes that that happened to him with a teddy bear once. He reveals that he does have the ascendant, and he offers it to Josie to prove that she can trust him. In response, she shows him that she already has the mora miserium in her bag. He’s pleased that she’s learning how to be devious.
Lizzie and Sebastian waltz at the mansion and continue to drag down the episode. He wants her to stay in the prison world with him, but she doesn’t want to ditch her family. She thinks she can eventually get Alaric to come around on him. Sebastian wants Lizzie to stay there with him.
Kai and Josie go to the hospital as she tells him abut Malivore and the Malivore pit. (She’s already told him about Santa, and Kai says he never lost faith that Santa was real. Good for him, considering there’s no way he ever made it on the nice list.) Josie explains that Malivore is a pocket dimension like the prison world. They closed the portal to it but monsters keep coming through anyway.
Kai tells Josie that he studied genealogical records for years and found a patient who donated blood under her married name Smithfield. Her maiden name was Bennett. But when they go to the storage room to get her blood, Jade’s beaten them there. Kai locks her in before she can try to feed on Josie again. He explains that since Jade, Wendy, and Diego were banished to the prison world like he was, they keep resurrecting, too.
That means Alaric, who’s just regained consciousness at the bar, could be in a lot of danger with Diego nearby. Wendy comes in and asks Diego to give Alaric a brief stay of execution. He put them on trial before he abandoned them in the prison world, and she wants to do the same to him.
Worried about Alaric, Josie wants to go find Diego, but Kai warns that since she and Alaric aren’t bound to the prison world, they can die permanently. He’s resigned to accepting that there’s no Bennett blood and they’re trapped there. Josie reveals that she has a vial of Bonnie’s blood with her. She didn’t want to let Kai know because she wasn’t sure if she could trust him.
Jade zooms up to them and pushes Kai up against a wall. He pretends to be scared, but the two of them start laughing. They’ve been working together the whole time. He does a spell to immobilize Josie and tells her that she was right not to trust him. “While you’ve been playing checkers, I’ve been playing chess,” he boasts. He takes the vial of Bonnie’s blood from her and says, “Checkmate.”
Kai confiscates Josie’s weapons as he tells her that Jade, Wendy, and Diego let him take charge after they woke him up. They’re basically his followers now. Great, just what someone like Kai needs – a cult following. He lets Josie keep the mora miserium, since he plans to be gone before it breaks. He assures her that she’ll get better at conning people. He instructs Jade to take Josie to Alaric and make both of them suffer before she kills them. “I couldn’t have done it without you, kid,” he tells Josie.
Lizzie and Sebastian talk about how quiet it is in the prison world. Still, there’s not enough there to make her want to stay. For one thing, she’ll age while Sebastian won’t. He suggests that she become a vampire so they can not age together.
Wendy strikes up a fire spell so she can torture Alaric, but he warns that he can take whatever she does to him. Jade arrives with Josie and wonders if he’ll be able to take seeing her get tortured. She wants an explanation for why Alaric sent the three students to the prison world. He says he didn’t have any other choice.
Ten years ago: Alaric shows Jade photos from the murder scene and asks what happened. She won’t answer. He reminds her that she’s a good person – she wants to be a doctor so she can help people. These murders aren’t her. She replies that he might not know the real her. Alaric notes that one of the victims was Inez, and he knows Jade has a picture of the two of them in her room. Why did Jade kill her? Jade says she wasn’t there, but the pin Alaric found at the scene is hers. It was in Inez’s hand. Jade tells Alaric he should go ahead and punish the three of them, since he’s already made up his mind that they’re guilty. After she leaves, he opens the box that holds the ascendant.
Present: Alaric insists that he did what he had to do. Five people were dead, and none of the three students admitted what they’d done or showed any remorse. He couldn’t let them go out into the world. That said, he made a mistake by sending them to the prison world. He should have killed them instead.
Jade laughs at him for “doubling down in the face of imminent death.” Alaric says that Caroline talked him into sparing their lives. Diego’s ready to kill him, but Jade still wants him to suffer. She sends Wendy and Diego to find Kai and make sure he has everything they need to leave the prison world. Once they’re gone, she starts to tell Alaric and Josie what really happened the night of the murders.
Ten years ago: Inez invited Jade to a party in the woods. They’d been flirting for a while, and Jade thought the party was a good chance to find out if Inez was really into girls. Wendy and Diego tagged along. It turns out to be a “freak party,” where attendees compete to see who can get the weirdest person to show up. As the Salvatore students are leaving, one of Inez’s friends throws a football at Diego. He starts to wolf out and goes after the thrower.
Present: Jade says she froze and couldn’t stop what happened. Or maybe part of her wanted there to be violence. She’s not completely sure what happened next.
Ten years ago: Wendy’s fire-conjuring abilities get out of her control and one girl is burned to death. Inez runs off, bloody from Diego’s victim, and Jade vamps out. She wasn’t aware before then that she’s a Ripper. She apologetically feeds on her crush.
Present: Alaric might think that Jade didn’t feel any remorse, but in fact, she was overwhelmed by it. She couldn’t take it, so she turned off her humanity. “I was screaming for help,” she tells Alaric. “You just couldn’t hear it.” She’s killed the other inhabitants of the prison world thousands of times, and now she’s finally the killer Alaric thought she was.
Alaric is sorry he didn’t recognize that Jade needed help. She says he was too busy protecting his daughters. He’s good at that, and she’d like to see how good. She undoes his chains and tells her to come with him so they can play a game.
Lizzie and Sebastian cuddle and drink wine at the mansion while she thinks about his invitation. She tells him she’s thought about becoming a vampire, since that would mean she and Josie wouldn’t have to merge (also, she’d always have the flawless skin she has now). But she wouldn’t be able to have kids or grow old with someone. She’s not even sure that’s what she wants, but the whole point is that she doesn’t want to take away that option when she’s not sure about her future.
Sebastian was afraid of that, and he tells Lizzie that he’s not actually giving her a choice. He put blood in her wine. He insists he did what he had to in order to keep her safe. Lizzie runs out, horrified.
Jade takes Alaric to the woods to play hide and seek with him. If he won’t cooperate, she’ll hurt Josie. She offers him a five-minute head start and tells him that if he can survive for 24 hours, she’ll let Josie live. Alaric reluctantly agrees.
Sebastian catches up to Lizzie and tells her he’s giving her the chance at immortality that Cassandra never got. If she can’t see that he’s trying to help her, he’ll have to make the choice for her. He loves her and won’t lose her again. He calls her Cassandra, then corrects himself. Lizzie kisses him, but it’s just so she can get a hold of him and siphon from him. He desiccates and falls to the ground. “I think we should see other people,” she says.
Wendy and Diego go looking for Kai at Fort Parker, where he’s left Jade a note. Wendy reads it, then title-drops, “Kai Parker screwed us.” He’s at the dock with the ascendant and the vial of Bonnie’s blood. Except when he pours the blood on the ascendant, nothing happens. Josie used a spell to make a mini-bottle of vodka look like a vial of blood. “Josie Saltzman screwed me,” Kai says. Overhead, there’s a meteor shower, the celestial event he could have used to get out.
Lizzie steals a police car and drives back to Vamp Villa with Sebastian in the backseat. At the bar, Josie gets a call from Kai. He claims he’s not mad about the trick she pulled with the blood – he’s even a little proud. Well, okay, he’s also mad, but that’s because he’s always mad, “in a fun, completely unpredictable sort of way. It keeps you on your toes.” Josie tells him she hates him, which Kai replies is a “Ric thing to say.” She says she’ll never help him leave the prison world or listen to anything he says. He tells her he called to help her get out. There’s another way. He confirms that she still has the mora miserium, because she’ll need all of the power inside it.
Diego shows Jade the note Kai left her, which just thanks her for all the sex. (She’s not too broken up about it, since she prefers girls. I imagine that having her emotions off helps soften the blow, too.) All she cares about is finding Alaric. She has Wendy do a locator spell, even though it’s cheating. (Music: “Crazy,” Nothing But Thieves covering Gnarls Barkley) It shows that he’s in the tunnels. Alaric, who’s almost always a step ahead, remembered that the tunnels could get him to the Armory in a fraction of the time it takes to drive there. And since the prison world is a snapshot of the real world back when Alaric ran the Armory, he knows where all his favorite weapons are.
Kai tells Josie that he’s found his own way out. He says she reminds him of Jo, who also thought she was smarter than Kai was. He punished her just like he’s going to punish his niece. To use the mora miserium, Josie will have to break it. When she gets hit with all the black magic inside, assuming it doesn’t kill her, it’ll turn her into “something dark and evil.” On the bright side, she’ll have enough power to make a door out of the prison world. In order to save herself and Alaric, is Josie willing to become a monster like Kai?
He adds that she won’t remember this conversation. In fact, she won’t remember him at all. Josie realizes where he is and what he’s about to do. Her stories about Malivore helped him figure out an escape plan. He’s in Georgia, where the Malivore pit was still full when the prison world was made. All he has to do is jump in. He’s fine with being trapped in a Hell dimension, alone, since it won’t be the first time.
Kai suggests that Josie smash the mora miserium ASAP, because he’s about to dive into the pit and erase himself. He’d hate for Josie to forget the only chance she has for escape. He wishes her luck, then falls backward into the pit. Everything goes slow-motion as Josie raises the mora miserium above her head and smashes it on the ground. She’s hit with the black magic inside, and Lizzie feels the effects as well and passes out. Josie ends up with black eyes and veins while Lizzie ends up unconscious, having crashed the police car.
In the Salvatore crypt, Kai climbs out of the new Malivore portal. The Necromancer greets him and asks who he is. He’s not like any monster the Necromancer has ever seen before. “Buddy, you don’t know the half of it,” Kai replies.
Etc.: Sending students – children – to the prison world with apparently no intention of letting them return to the real world seems cruel even for Alaric. He hasn’t worked out some sort of supernatural rehab program for them?
Not sure about the beard on Kai. They don’t have razors in the prison world?
LOL at Sebastian giving Lizzie keys to the mansion, like, you don’t need keys in a prison world where only five people live, my man.
Since the prison world consists of the same day repeating over and over, wouldn’t resources used up one day just be replenished the next? Wouldn’t they just have to wait until the next day for the Bennett blood to reappear?
The last four minutes of the episode are so well done. This is probably the best use of music in the whole series.
An Eternity of Misery 