A bartender is closing up Scull Bar for the night when a vampire starts zooming around, knocking over a bottle of alcohol and dropping the bartender’s co-worker onto the bar from the balcony. The vampire is Caroline, and Stefan boos her for her attempts to scare the bartender. They made a bet about whether Caroline could scare him to death, and Stefan says she went too cliché with her first attempt.
Caroline steps it up, compelling the bartender to believe he’s having a heart attack. Stefan accuses her of cheating and tries to calm the guy, but Caroline makes him believe he’s choking and covered in spiders. Eventually she scares him into a heart attack. Stefan argues that it’s a loophole and doesn’t count, but Caroline insists that she won. Her prize is karaoke.
The next day, Enzo takes Sarah to Vamp Villa, planning to hand her over to Damon and make her his problem. Lily comes to the door and Enzo freezes up. He lies that they accidentally came to the wrong house. As they’re speeding off, Enzo tells Sarah that he met Lily in 1903. In fact, she’s the person who turned him.
Damon and Elena are getting ready for the day together (as much as they can when they can’t keep their hands off of each other) when they realize that Lily’s cooking breakfast. Elena urges Damon to give his mother a chance, just like Elena gave him one. Damon still doesn’t want to think of Lily as anything other than a way to get Stefan’s humanity back. He’s eager to put her to use and get their “supernatural-born killers out of circulation.” Elena goes looking for a shirt in Damon’s dresser, but he stops her from opening it, not wanting her to see that he’s stashed the cure there.
Lily has made Damon’s favorite breakfast as a child, “eggie in baskie.” Lily, I’m going to need you to say that again when Bonnie’s around. She needs to hear it. She mentions that Elena’s only been a vampire for a few years and asks if she misses being human. Elena casually says she does sometimes. Lily asks about the ascendant they’ll need to get her family out of the 1903 prison world (along with a celestial event). Damon is nonchalant about all that, but Lily has looked up a couple of possible events, having already familiarized herself with the Internet. She’s amazed by all the knowledge it contains. “And videos of cats riding robot vacuum cleaners,” Damon adds. Elena heads out when she gets a text from Jo letting her know that Stefan and Caroline have been attacking people at Whitmore.
Back in Enzo’s car, Sarah wants more information about Enzo and Lily and how Enzo knows who her family is. He tells her that Stefan compelled her to forget stuff she’d learned, to protect her from Damon. But now the good brother has gone bad and the bad brother is less bad than the good brother. Yeah, that doesn’t help. Anyway, here’s a flashback no one cares about!
1903: Enzo is trying to board a ship in South Hampton, England, but he’s not allowed since he’s sick. Lily finds him and offers to take him to a doctor.
Present: Enzo thought he was being helped by a classy woman who was going to lead him to a new life. By the time the ship docked in New York, everyone on board was dead, including Enzo. He compels Sarah to forget all about the Salvatores…but it doesn’t work. Someone’s been taking vervain! (Thanks, Matt!) She injects a syringe of it into Enzo’s neck and knocks him out.
Caroline and Stefan have taken over Scull Bar so she can do karaoke. She sings “Hit Me With Your Best Shot” for an audience of compelled students. One who must have missed being compelled complains and asks for the manager. She gets Stefan instead. Matt and Tyler come by on a break from training for the law enforcement program Matt got them into and quickly see that it’s not a good place for them to be right now. Stefan tells them to stick around, since Caroline’s taking requests.
Damon heads to Whitmore with Lily, who experiences a modern car and texting for the first time. She recaps the plan: Get Stefan to flip his switch, then go to 1903 to get her friends. Damon pretends he’s on board for that. Lily’s texting Elena for him and she asks if she should end the message with “I love you.” He does love her, right? Damon says it’s not Lily’s business, but yes.
She thinks he’s afraid of disrupting their relationship if he gives Elena the cure. Turns out Lily was eavesdropping when Damon discussed this with Bonnie. He asks her to keep it quiet, saying he’s not even sure if Elena wants the cure. Lily guesses that he’s afraid she does, and that she’ll leave him if he gives it to her. Lily notes that she and Damon are a lot alike – neither of them wants to be alone.
Elena helps Jo with some of Stefan and Caroline’s victims, hoping Damon and Lily find them soon and fix everything. Jo was unaware that Lily was alive, or that she spent the past 110+ years in a prison world, or that Kai is now trapped there. (She’s been working a really long shift and would have appreciated a text from the gang.) Elena assures her that Kai’s gone for good. She notices Jo putting her hands on her stomach and realizes she’s pregnant. “The last thing this baby needs is an Uncle Psychopath,” Jo says of Kai. Elena’s thrilled for her and Alaric, but also a little sad that she’ll never be able to have a baby herself.
Enzo wakes up in a photography studio, where Sarah confronts him for that whole thing with Matt in the tunnel, which she learned about from snooping through his texts. She can’t believe she ever trusted Enzo. He can relate to being naïve.
1903: Enzo’s dying, and the doctor on board the ship warns that the only treatment available to him right now is expensive. Lily says that’s not an issue, but when she compels the doctor to say how many people he’s saved, he admits that the cure is just a placebo. Enzo will be dead within the week. Lily sends the doctor away, and Enzo encourages her to leave, too, so he doesn’t get her sick. She tells him she can’t, since she already had consumption. He wonders how she survived it – is she an angel?
Present: Caroline has finished another karaoke performance, and Tyler thinks he and Matt have sufficiently fulfilled their roles as audience members and should be released. The rest of the audience has already been dismissed. Caroline wants to play a trivia game with her two exes, challenging them to stay alive by answering questions about her. Tyler gets her birthday right (October 10th) and Matt sees through a trick question about her favorite color (she doesn’t have one). For the tiebreaker, what was Liz’s final memory before she died? The guys have no idea, but Stefan does. Caroline says there’s no winner, so she and Stefan will just kill both Tyler and Matt.
Some more victims turn up at the medical center, and Elena admits to Jo that she’s not shocked by Caroline and Stefan’s behavior. She did the same things herself, after all. This is just a reminder that there will always be a part of her capable of hurting people. Jo tells her she won’t let it happen. Elena will have plenty to keep her busy in life, like her thriving family medical practice. Elena notes that she won’t be able to stay in one place for too long before people notice that she hasn’t aged.
Jo asks if she’s talked to Damon about her concerns. She knows Elena’s having complicated feelings about her loss of humanity and her inability to have children. Elena says she’s just happy for Jo and Alaric. Jo notes that Alaric used to be a vampire and is now human again. Elena says that Damon knows how she feels, but there’s nothing they can do to change things, so nothing can come from dwelling on it.
Sarah asks Enzo how she knows he’s not the one who’s been messing with her mind. He thinks she’s fascinated by morbid things, as evidenced by her photography preferences, because she has emotional scars from the circumstances of her birth – being delivered out of a dead woman. She admits to finding death interesting. Enzo tells her she can’t really appreciate it until she’s been close to it.
1903: Lily tends to Enzo like he’s her child, something he’s not used to. He was abandoned as a child and has never had anyone care for him with kindness. She can relate, since Giuseppe sent her to a TB ward to die. She felt free once she was given a reprieve, like she was released from a life that didn’t want her. She found her true family then. They’re outcasts like Lily and Enzo, and Enzo could join them and never be alone again. He thinks he’s nearing the end of his life, but Lily says it could be a beginning. She cuts herself and drips blood in a glass for him to drink.
Present: Elena texts Damon to tell him that Stefan and Caroline are at Scull Bar. Lily wonders if there’s a plan B in case she can’t get Stefan doesn’t remember her. Damon thinks she’s not sure she can get him to flip his switch. He suggests that she channel the emotions she was feeling when she came back to get them in 1903. Lily’s confused about that – she didn’t come back to the U.S. from Europe to get her children. Damon tries to brush that off and encourages Lily to connect with Stefan.
She’s frustrated, though, since she hasn’t been their mother in a century and a half. She’s only felt fear about what she might do if she saw them again. She had to find others who could guide her back to herself. By the time they did, she’d lost everything she felt for her sons. “I hate that I can’t make myself feel more,” she admits.
Caroline flips a coin, deciding that if it comes up heads, she’ll kill Tyler first. Tyler knocks the coin out of her hands before she can show him the results. He taunts her and Stefan for pretending they’re brave for messing with people who are afraid of them. He breaks a chair and throws part of it at Stefan, who just laughs. Tyler asks if he’s not used to people fighting back. “No, actually, I’m just not used to people being this stupid,” Stefan replies.
Matt tries to make peace but Caroline eggs Tyler on. He arms himself with a stake and invites the vampires to come after him. Stefan offers to kill Tyler for Caroline but she wants to do it herself. She dares Tyler to attack her. Matt again tries to make peace but Tyler ignores him. He swings the stake at Caroline, but she grabs Matt and pulls him in front of her so he takes it instead. Stefan’s amused. “Nice going, Tyler,” Caroline says sarcastically.
Damon calls Elena to tell her that Lily basically said she doesn’t love her sons. He downplays how that makes him feel, pointing out that he wasn’t going to hold up his end of their deal, so they’re even. “150 years is a long time to care,” he notes. Elena reminds him that he spent almost that long pining for Katherine. She wants him to know that it’s okay to be hurt. Lily and Katherine both abandoned him. He replies that at least Elena never has. He wants to come up with a plan B, but Elena points out that Stefan doesn’t know how Lily feels (or doesn’t feel) about him. If she can fake it, he might buy it.
Damon tells Lily that she’s Stefan’s only hope, so if she doesn’t put on a show for him, she’ll never see her other family again. He’s confident that she can pull this off. Lily wants assurance that Damon will get her back to 1903 even if she fails with Stefan. She can’t believe all his promises that he will – after all, he’s keeping something from his girlfriend. As a show of good faith, Damon gives her the 1903 ascendant.
Sarah thinks Enzo’s miraculous rescue was a pretty good deal. He tells her it comes with the side effect of deep hunger.
1903: Enzo wakes up in transition, surrounded by a bunch of dead people. The doctor tells him that Lily killed them all and sent him so Enzo can feed on him and complete his transition. Enzo does it with the intensity of a Ripper.
Present: Enzo tells Sarah that he searched the ship for Lily, but she and her family were gone. She never gave him the new life she offered him. “She made me a monster and then abandoned me,” Enzo says. He figures it was just part of some game she liked to play. Sarah compares it to the game he played with her. He confirms that he wanted to do the same thing to her that Lily did to him. He wanted to make her a monster.
Tyler tries to help Matt as Caroline wonders if Matt’s death would trigger Tyler’s werewolf curse. Stefan says this could be nature’s way of getting him to reconnect with his true self. Damon and Lily arrive just then, and Lily has no reason to worry that Stefan won’t remember her – he immediately recognizes her. As Tyler takes Matt to get medical attention, Stefan accuses Damon of making a dumb attempt to get him to flip his switch. After all, Lily’s dead. Caroline knows that this is just the first step; once Stefan’s humanity is back, he’ll get her to take hers back, too. Not wanting to stick around for that, she immobilizes Stefan with a stake to the back, then zooms out.
Tyler gets Matt to the medical center, where Elena starts to heal him with her blood. He refuses it and asks for a doctor instead. Back at Scull Bar, Lily removes Stefan’s stake, which allows him to try to run away. Damon stops him. Lily announces that she’s a Ripper, so she’s the reason Stefan is the way he is. That’s why she had to leave – she couldn’t be sure she could keep herself from hurting her sons. The day of her funeral, she visited Stefan, who mistook her for an angel.
A flashback shows that Damon has told her exactly what to say. She repeats his words, saying she wishes she’d been there to watch Stefan grow up, to protect him from Giuseppe. But she was ashamed of her actions and who she’d become. When she got herself under control and came back to the U.S. to see her sons, the Gemini coven captured her. The only thing that got her through her time in the prison world was the hope of seeing her children again. Lily knows she can’t make up for abandoning them, but they have eternity to repair their relationship. “Your angel has returned to you,” she tells Stefan, the same words Damon fed her. She promises to never leave him again.
Stefan closes his eyes and turns his humanity back on. Damon’s quietly pleased. Now begins the part of the Ripper cycle where Stefan starts feeling guilty for what he’s done, but Damon will only give him the night to do that before he has to find Caroline. Stefan says he doesn’t need the night – he’ll go after her right now.
Elena checks on Matt, who says he didn’t want vampire blood because he can’t risk dying with it in his system. He has a bad history of dying or almost dying, often because of vampires he considers friends. Elena protests, but as she mentioned to Jo earlier, Matt knows she’s just a flip of a switch from being someone who could hurt him. She surprises him by saying that he has a right to be mad. She just wishes he would let her make him better. Matt’s decided that he can’t hate vampires but also take advantage of their perks.
Enzo determines that the vervain is out of Sarah’s system, so it’s time to compel her to disappear somewhere. She asks for the choice he was never given. He wants her to be safe, but she doesn’t want this forced on her. She promises to stay away from the Salvatores, so he gives in, sending her off to do whatever she wants as long as it’s not around vampires.
Damon and Elena meet up outside Scull Bar, where she announces that she wants to throw Jo a baby shower. They should celebrate the best news the gang has gotten in a while. (Uh, Bonnie’s back. That’s good news.) She admits that she didn’t react the way she wanted to because she was a little jealous. She’s always wanted a family, or at least she did before she turned. Now she has to remember that it won’t happen for her. But on the plus side, she gets to have a life with Damon, something else she’s always wanted. She just needs a little time to be sad before she’s happy again.
“What if things could be different?” Damon asks. “What if you could change everything?” Elena says it’s not possible, so it doesn’t matter. Instead of telling her that it does, he just says he loves her. Their nice moment is interrupted when Jo summons them back to the medical center. She called Joshua to tell him Kai’s been banished again, and he asked where the 1903 ascendant is. Jo wants to destroy it. Damon says he gave it to Lily, and Jo tells him to get it back ASAP.
As Lily studies the ascendant at Vamp Villa, Jo explains that her buddies from 1903 are witches who were cast out of the Gemini coven. They’re called Heretics. Like Kai, they siphon magic. Lily turned them, but unlike most witches who become vampires, they didn’t lose their ability to use magic. They’re able to siphon magic from themselves since their vampirism gives them a constant source of it. Think of them as vampire/witch hybrids. The Heretics were on their way to attack the Gemini coven, who exiled them to the 1903 prison world.
1903: Lily goes to the ship’s cargo hold, where her Heretic buddies are freeing themselves from their storage crates.
Present: Jo tells Damon and Elena that Heretics are ruthless and shouldn’t be let out of the prison world. Imagine Kai but with a vampire’s bloodlust. Now multiply that by six. Yep, definitely not something you want running loose in the world. It’s a good thing they’re stuck in a prison world and can’t get out! That would be super-bad!
Keep in mind: Heretics are both vampires and witches. They siphon their own magic, giving them an endless source of power.
Etc.: Writers, seriously, NO ONE CARES about Enzo’s backstory.
I want to see Damon watching cat videos. I want to see him unable to pretend he doesn’t like at least one of them.
Thank you, Matt, for being smart and providing Sarah with vervain. Please do that for people more often.
Lily, composing a text to Elena: “My dearest Elena, I hope this finds you well.” I’m going to start texting like that.
Tyler, sweetie, you’re human again. Don’t pick fights with vampires.
Let’s not think about how much Lily is like Katherine, in that she turned Enzo and then ditched him. That borders on territory a psychiatrist would have a field day with. (Oh, Cami…)