You can tell Damon’s going through a tough time because he’s lying in the middle of a road at night. A guy named Cooper comes across him and helps him up, asking why he’s there. Damon says he thought it would make him feel better. He asks Cooper if he’s ever done anything so horrible that it makes him sick to see his own reflection. Compelled to be honest, Cooper admits that he accidentally killed his girlfriend’s cat and didn’t tell her. Damon wins this one, since burning Elena’s coffin is arguably worse.
He hitches a ride with Cooper, who’s forced to listen as Damon says that he thought being with Elena would make him a better person. But it was always going to end up this way, with him destroying her. He knows from his time in the phoenix stone that he’s “permanently damaged goods.” Cooper can’t relate. Damon casually says he’s going to kill him now. It’s nothing personal; he’s just a meal. Damon doesn’t see himself caring about anyone ever again. He bites Cooper, then tosses him out of the car and drives off.
Dear Elena, Caroline hasn’t written in a while because she’s been a little busy with her supernatural pregnancy and her boyfriend’s post-phoenix stone hallucinations and worries about Damon. Stefan shows up with lunch as she’s writing a journal entry. The twins suddenly get really active and Caroline starts feeling weird, then passes out.
Penny questions Matt about his bag of weapons, which he claims he confiscated from some “zombie apocalypse survivalists.” This makes sense to her, since she’s heard that people in Mystic Falls are a little crazy. She releases him from lock-up, telling him that his phone keeps buzzing with notifications from matchasingle.com. She’s also on the dating app but hasn’t gotten any matches. She tells Matt that she didn’t book him on any charges last night, so there won’t be any record of this. Plus, she heard that Mystic Falls citizens are getting calls saying they’re allowed to return to their homes. That’s news to Matt.
Julian is still running things in Mystic Falls, and it’s still a non-stop biker rally/town-wide party. He’s bringing people back so they can invite vampires into their homes and the vampires can take over. Valerie shows up at his new headquarters, the Grill, and notes that he’s surrounded by “degenerate yes-men” who make him feel safe. She knocks out that feeling by giving him a postcard she got by mistake. It’s the same X-marked card that spooked Nora.
Speaking of Nora, she and Bonnie are doing a spell to locate the huntress who send the postcard. Bonnie doesn’t get why a vampire hunter would announce her intentions before going after her target. Mary Louise joins them and says this huntress, Rayna Cruz, is different. She likes to taunt her victims beforehand, “like a cat nibbling the legs off a spider.” Mary Louise also received a postcard, and though she doesn’t think Julian got one, she told him they would take care of the problem. Bonnie tells her that Rayna is in Cincinnati. Though the three witches aren’t on great terms and don’t trust each other, they agree to go find her together.
Julian burns his postcard, pleasing Valerie by looking scared. She notes that he just made himself at home in Mystic Falls, and now he’ll have to run. Julian offers a vampire named Kyle a car if he kills Valerie. Kyle won’t be able to follow through, though, since he’s just been decapitated by Damon. Damon’s directly defying Julian’s threats not to hurt any more of his men, and he definitely wants to pick a fight.
Stefan takes Caroline to Whitmore’s medical center, where a doctor assures him that she and the babies are fine. Stefan has to explain that he’s Caroline’s boyfriend, but not the babies’ father (Alaric is in Dallas for a job interview). When he goes in to see Caroline, they notice that her hand is desiccating.
Julian invites Damon to share any last words he might have before Julian kills him. Damon says that’s a lot of pressure. He asks about the “X-marks-the-spot postcard” and who Julian’s running from. Julian thinks he should come up with something more poetic in the next two seconds. Damon mockingly asks if he’s scared of the huntress who sent him to Hell.
Julian attacks him, ready to stake him with a broken pool cue, but he stops himself because he knows Damon’s in a “self-destructive spiral” from his time in the phoenix stone. Lily was Julian’s touchstone, keeping him tied to his sanity; he lost control when he lost her. He guesses that Damon is now spiraling because he lost his “epic love in the box.” Damon admits that he burned Elena alive. Julian drops the pool cue and suggests that Damon have some fun to get his mind off the pain he must be feeling.
Nora and Bonnie share junk food on their drive to Cincinnati, bugging Mary Louise, who can’t believe her ex is eating that garbage. Bonnie asks how Rayna is still alive if she was around in the 19th century. Nora explains that she was spelled by shamans to be a huntress. They gave her super-strength and the phoenix sword, so they must have tacked on an extended lifespan. Nora reminds Bonnie of the Everlastings, something they read about in class (I assume Alaric’s). Mary Louise pretends not to be jealous that they’re “study buddies” now.
Valerie goes to the hospital to try to figure out what’s going on with Caroline. When she puts her hand over Caroline’s stomach, there’s a red glow and Caroline’s desiccation disappears. Valerie tells her and Stefan that she didn’t do anything. She thinks the babies can siphon magic like the Heretics and their Uncle Kai. The problem is that they’re siphoning the magic from Caroline’s vampirism, and we know from the Travelers’ spell at the border that removing magic from a vampire kills them.
Bonnie, Nora, and Mary Louise arrive at Rayna’s location, a hospital for the criminally insane. Bonnie asks if they’re going with any kind of plan here. Mary Louise says she and Nora will kill Rayna, and Bonnie can just watch from the sidelines. Nora thinks Bonnie should help, since she has a lot of power. But they may not need much power, since Rayna is an elderly woman confined to a bed.
Julian takes Damon to an alley where he’s set up what can only be described as a vampire fight club. He lets vampires spar for housing and meals (AKA the houses’ owners). The losers get killed. Julian believes violence is the best medicine when it comes to anguish. If Damon really wants to feel pain, he should get in the ring.
Matt heads to the house of someone who was recently summoned back to town and finds the owner dead. Penny appears and admits that she followed Matt. She demands to know what’s going on. A vampire shows up and Penny tries to shoot him, but Matt has to finish him off since Penny’s bullets aren’t made of wood.
Valerie gives Caroline a talisman full of magic, hoping the babies will siphon it instead of Caroline. If it doesn’t work, Valerie will get something stronger. She promises not to let anything bad happen. Caroline is truly grateful for Valerie’s help, especially since the two of them haven’t gotten along before now. Valerie tells Stefan that she thinks the babies have been siphoning Caroline’s magic for a while without her noticing. There’s probably nothing to worry about.
She asks if he’s talked to Damon. Stefan says Damon hasn’t been returning his calls. Valerie tells him that she saw Damon at the Grill, looking like he wanted to get into something with Julian. Stefan’s not happy to hear that Damon killed another one of Julian’s vampires. Valerie says he may have a death wish. Damon’s in the ring now, fighting the most recent winner of a sparring match. He pulls out the guy’s heart and asks for another opponent.
Bonnie, Mary Louise, and Nora introduce themselves to the woman they think is Rayna. She doesn’t remember the latter two, despite chasing them across Europe for decades. She also doesn’t know what the X-marked postcards are about. She just wants a cookie. The witches step outside her room and debate whether they have the right person. Mary Louise wants to kill her just to be on the safe side, but Bonnie and Nora decide to keep searching for the real Rayna. Mary Louise is annoyed that they’re siding with each other. Bonnie is, too, and she tells Nora to go search with Mary Louise. She doesn’t like that Nora is using her to make Mary Louise jealous.
Damon faces off with an undefeated vampire named Samson. “Perhaps the pain he inflicts will finally feel like atonement,” Julian says. Damon puts up a good fight but ends up at Samson’s mercy. At the last minute, someone tosses a stake into the ring and Damon is able to kill his opponent. Julian’s mad, since there’s a rule against weapons. Looks like a groupie took an interest in Damon and wanted to make sure he stayed alive. Julian tells Damon to call it a night but Damon wants another fight. Julian offers himself as the next opponent. Stefan arrives just then and tries to talk Damon out of fighting Julian. Damon ignores him and gets back in the ring.
Valerie keeps Caroline company/distracted while Stefan deals with Damon and Julian. Caroline’s annoyed that Valerie won’t take matters into her own hands instead of letting Stefan take Julian on. She thinks Valerie wants Stefan to prove that he still cares about her by defending her honor. Caroline tells Valerie to go look after Stefan instead of keeping an eye on her.
Stefan again tries to talk Damon out of fighting Julian, who’s 300 years older. He thinks Damon’s still feeling the aftereffects of the phoenix stone, so he’s making bad decisions. Damon says he deserves this, and if Stefan doesn’t back off, Damon will destroy him like he’s destroyed everything good he’s ever touched. Stefan realizes that something happened, but Damon won’t tell him what it is. Julian has Stefan removed from the arena so he can’t interfere with the fight.
Bonnie brings Rayna a cookie and is rewarded with confirmation that she’s the huntress they’re looking for. She says she became careless as she aged. Her drive to kill, which the shamans placed in her, got a little mixed up, and she killed a human by mistake. Her arms are restrained, so she asks Bonnie to help her with the cookie, but it’s a ruse to get Bonnie close so Rayna can grab her by her visitor’s lanyard. Bonnie tries to do a spell to free herself but Rayna says magic doesn’t work on her. She orders Bonnie to undo her restraints. Before Bonnie can, someone appears in the doorway and chucks a knife into Rayna’s throat. It’s Enzo.
Damon and Julian’s fight begins as Julian comments that it seems like he was lucky to be an only child, since Damon and Stefan have so many issues. Damon thinks that’s why Julian has to surround himself with minions – he doesn’t want to be lonely. Julian taunts that at least he has friends. Damon’s driven away everyone who’s ever cared about him. Julian punches him a bunch of times as Damon looks out into the crowd for Stefan. Julian says that even if Stefan did come back, he’d hate Damon when he found out what he did to Elena.
Damon eggs Julian on to kill him already. Julian asks if he’s sure he’s ready, and Damon says yes. Julian reaches into his chest…then puts his hands to his head because he has a magic migraine. Stefan and Valerie appear in the ring, having snuck in under a cloaking spell.
Stefan tells Damon that if he lets Julian kill him, Stefan will then kill Julian, which will lead to Stefan getting killed by the crowd. He doesn’t think Damon cares; he doesn’t believe that his or Stefan’s lives matter. But when Stefan offers Damon his hand, Damon lets Stefan help him up. As they leave the ring, Valerie ends Julian’s magic migraine. He tells the crowd to kill the brothers if they come back.
Bonnie asks Enzo where he’s been (not because she missed him. She definitely didn’t miss him). He’s surprised that Matt didn’t tell her about the group he called in to come capture Enzo. They undo Rayna’s restraints so they can get her body out of the hospital. But when Bonnie returns after collecting Nora and Mary Louise, Enzo and Rayna are both gone.
Stefan wants Damon to talk about what happened in the ring. Damon just pretends that the “intervention” worked and he now sees that letting Julian kill him would have been a mistake. Stefan thinks Damon’s going to walk away now and flip his switch. Damon says he actually wants to feel everything right now – he wants to experience all the misery of his miserable life. He admits that he burned Elena’s body. He challenges Stefan to stand by him once again after this most recent misdeed. Stefan punches him a few times, then walks off.
He cries a little in his car, then beats the steering wheel in anger. Valerie joins him and offers to drive him back to the hospital, since Stefan doesn’t seem up to it. He tells her this is Julian’s fault. He took Lily away from her kids, hurt Valerie, killed their child, destroyed Damon, and took over Mystic Falls and Vamp Villa. Yet Stefan keeps letting him live. Valerie thinks that’s the smart thing to do, since Julian is strong and has a ton of protection. Damon might not get that they shouldn’t poke the bear, but Stefan is smarter. “I don’t want to be the smart one anymore,” Stefan replies. “I want him dead.”
Matt has told Penny about the vampires in Mystic Falls and is waiting for her to process the news. She threatens to punch him in the face if he says, “Penny for your thoughts.” Heh. She thinks he’s crazy – not for believing in the supernatural but for staying in a town full of monsters. Matt says that he doesn’t talk to his parents and his sister is dead, so Mystic Falls is his only constant. Plus, once you know the supernatural is real, you can’t really hide. You might as well take a stand. Penny tells him that he’s completely different from how she thought he was when they first met. She didn’t know how brave he was.
Mary Louise finds Nora at a diner and thanks her for helping to make the day a success. She thinks the two of them still make a good team. She asks if Nora likes Bonnie. Nora says that Bonnie’s beautiful, smart and loyal, while Mary Louise is only two of those things. Mary Louise regrets choosing Julian; if she could take it back, she would side with Nora every time. She loves Nora and hopes Nora will forgive her someday. As Mary Louise is leaving, Nora says they do still make a good team.
Caroline texts Stefan to call her when he gets the chance. She encourages the twins to have some self-control so they can stay in utero a little longer. But they don’t listen, and now she’s desiccating again. She’s unable to reach her phone to call Stefan.
He probably wouldn’t pick up anyway, since he’s gone to the Grill to confront Julian. Julian taunts that Damon is too far gone for rehabilitation. Stefan agrees. He stabs something into Julian’s hand and says it’s Julian’s fault for sending Damon into the phoenix stone. Julian notes that Stefan is making a mistake by attacking Julian in front of his minions. But Valerie has cloaked them, so no one can see as she immobilizes Julian with magic to allow Stefan to stake him. Stefan looks Julian right in the eyes as he kills him, with Valerie the only witness.
Krystal, the groupie who tossed Damon a stake, tracks him down at Lockwood Landing and offers him some tequila. They make out, since Damon doesn’t need to be faithful anymore. Enzo has taken Rayna to a place we’ll later learn is called the Armory. He villain-monologues to himself that he sent the postcards to the Heretics knowing that the witches would lead him to Rayna. Rayna’s body goes up in flames in a room surrounded by glass, and a younger woman emerges from the smoke.
Three years from now: Stefan finally arrives at the news station. Matt tells him that he got Caroline out, but Damon’s inside. Matt disabled the security cameras outside but isn’t sure if he needs to do anything with the ones on the roof. When Stefan isn’t looking, Matt injects him with vervain. He looks into a security camera and says he did what he was supposed to, and he wants to confirm that he’ll never see the person he’s speaking to again. It’s Rayna – the younger version – and she tells him to go have a nice life. Then she turns her sights to Damon.
Keep in mind: The twins can siphon magic.
Etc.: Valerie is an underrated character. The guts she has to go see Julian on her own after what he did to her…she’s tough.
Rayna is one of my least favorite villains from the three series. I don’t think she’s written well. And no offense to Leslie-Anne Huff but I don’t think she was right for the role.
Matt’s cover story for his weapons is pretty good, actually. I would buy it if I were Penny.
I hate the fight-club stuff. It feels like filler because they didn’t know what else to do and wanted to throw in some stunts.
I wish Valerie had gotten to kill Julian. It would have been much more satisfying.
An Eternity of Misery 