Caroline’s humanity may be off but she still has manners, which is why she’s cleaning up the mess she made at Scull Bar. Enzo comes in and questions why she’s bothering. She points out that she can’t have people getting suspicious of her. Not only would the police and Whitmore take action but the gang would lock her up. She needs to keep her freedom so she can audition for the school musical the next day. Enzo’s there to get his phone, which Caroline stole. She tells him she used Sarah to get Stefan to flip his switch. Then she leaves him to finish cleaning up the bar.
Stefan goes home to Vamp Villa, where Damon is waiting for him like he’s Stefan’s father and wants to know why he missed curfew. Damon asks if there’s anything his brother would like to share. “Where do we keep our weapons?” Stefan replies. He starts to gather some, stopping only because Damon rushes him with a syringe full of vervain. He’s not surprised that Elena told Damon that he turned off his humanity. He tells his brother to stay out of his way.
Sarah spent the night at the medical center, and when she wakes up, Jo tells her that she got drunk and turned up on the quad. She doesn’t like using the hospital as a “supernatural holding cell,” but Alaric notes that there’s hardly anyone around, since it’s spring break. Plus, they can’t run the risk of anyone killing Sarah while she still has Elena’s blood in her system. They don’t need any more Salvatore vampires. Soon Sarah will be back at Duke with no memory of what happened. I’m sure everything will go exactly according to plan! Jo considers Duke as a baby name, and Alaric pretends he’s been brainstorming some himself. She doesn’t believe him, and she shouldn’t, because all he can come up with is Josette Jr.
Elena finds Damon taking out his rage on furniture and lamps at Vamp Villa. He dreads the inevitability of Stefan going Ripper, then feeling guilty for a year for each person he kills. Elena notes that since Stefan was Caroline’s emotional trigger, they now don’t have a way to get her back. Damon gives her his smashing weapon before he can use it on the video camera. He shows her Bonnie’s video and tells her that the woman in it is his mother. As he lists all the things he’s learned, Elena can only focus on the fact that Lily is alive.
Damon tells her Lily’s a Ripper, which makes sense to him since Stefan was always a mama’s boy. Elena realizes that that might work to their advantage – Lily could be an emotional trigger for Stefan. Damon says that Lily killed so many people, the Gemini coven put her in “permanent timeout.” They can’t fix one Ripper problem by releasing another. But Elena thinks they should try, since they could get Stefan, Caroline, and Lily back all at once. She asks if Damon isn’t even a little curious to see his mother again.
Damon comes around on the idea, but Bonnie isn’t on board to help since it means working with Kai. She can’t believe Damon is coming to her less than 24 hours after she told him how much she hates Kai. Damon promises that if the plan goes right, everyone will win. Bonnie agrees to give him some of her blood if he’ll go away. He’s fine with that but thinks he has a solution to her bigger problem.
He sends her to Kai to get the 1903 ascendant, which he happens to have on him. He looked for it when Damon told him about Lily. Fun fact: As the leader of the Gemini coven, Kai doesn’t need a celestial event to travel between prison worlds. How convenient! But he’ll only help the gang if Bonnie goes along on the trip. “I would rather die of cholera than spend an afternoon with you,” she tells him. Kai warns that Caroline’s probably a bigger threat.
It’s time for Caroline’s big audition, where she sings “Still Hurting” from The Last Five Years. She even throws in some fake tears. The director doesn’t respond when she’s done, but it’s not because of her performance – it’s because Stefan has torn off his head. He criticizes Caroline’s lack of authenticity and her desire to keep her facade as the good girl so she doesn’t have anything to make up for after her year without humanity is up. Well, except for the fact that she ruined Stefan’s life.
Unlike Caroline, Stefan isn’t going to keep himself in check. If his life is going to fall apart when he gets his humanity back, he’s going to take her down with him. He taunts that he’s her worst nightmare as a control freak – he’s upsetting her routine and forcing her to let go until she breaks.
Damon, Elena, Bonnie, and Kai gather at Vamp Villa so they can travel to 1903 together. Elena hopes she’s dressed appropriately to meet her boyfriend’s mother. Damon doesn’t want her to come along, and Kai points out that travel is harder the more people there are. Bonnie reminds him that she’s coming, too, so they can handle it. Kai activates the ascendant and the group quickly arrives in 1903. The witches send Damon and Elena to get Lily while they look for the ascendant (since ascendants can’t travel between prison worlds, they need another one to send them home). Elena’s hesitant to leave Bonnie alone with Kai, but Bonnie says she’ll be fine.
Stefan tries to leave Whitmore but discovers that his motorcycle has been dismantled. It’s Caroline’s revenge for killing the director. She won’t tell him again to go away. Stefan taunts that she’s bad at retaliation – all she did was unbolt the bike, which will only take him a few minutes to fix. “You’re an embarrassment to humanity-free vampires everywhere,” he tells her. Caroline gets a little more creative, punching a hole in his gas tank. I think he’s a little proud of her for that.
Alaric is trying to come up with baby names when Jo calls to tell him that since he has a ridiculous name, she’s revoking his right to choose one for another human being. As he points out, he didn’t pick his own name, so she grants him veto power. He immediately vetoes Duke. Heh.
Enzo comes by his office to tell him to grab some vervain and get Caroline and Stefan to the basement of Vamp Villa. Alaric reminds Enzo that he’s human now, so he can’t do that alone. Enzo thinks he’s just gone soft because he’s an expectant father. Alaric says he wants to stay alive for his child. Enzo thinks the kid would be better off without a coward for a dad. This does the trick and Alaric agrees to grab some weapons.
Elena takes a look around Lily’s 1903 home, the house that Stefan and Damon grew up in. Damon tells her to stop looking at baby pictures and remember their mission. They need to get the ascendant, get Lily, have her make Stefan flip his switch, and then figure out what to do with her. Elena suggests giving her a second chance, but Damon isn’t going to grant one to a mass murderer. She reminds him that Stefan was a Ripper and Damon never gave up on him. Since Lily let her sons believe she was dead, Damon doesn’t think she deserves forgiveness. He considers her dead since the day they buried her empty coffin.
Lily comes in and is shocked to see Damon. She tells him and Elena that she turned in 1858, when a nurse in a TB ward gave her vampire blood. Damon wishes she’d bothered to come home and tell her sons she wasn’t really dead. Elena asks Lily (“Mrs. Salvatore,” which Damon knocks her for) how she ended up in the prison world. Lily says she arrived in New York on October 31st, 1903, and was attacked by a coven of witches. When she woke up, she was alone. Damon notes that she must have made a lot of people really mad.
He notices an eyedropper with some blood on it and asks if Lily’s on a diet. She tells him she’s cleaned out every butcher shop from New York to Virginia and only has a little blood left. She only gives herself two drops a week to stay awake. Elena is sympathetic but Damon isn’t. Lily knows that Stefan and Damon turned during the Civil War and says their father must have been furious. “He was. And then Stefan ripped his throat out,” Damon replies. Lily’s proud of him for that – she despised Giuseppe. That just makes it worse that she left her children with him when she left to “join the Ripper coalition.” Lily says it’s nice that Damon has grown into himself. She asks how Stefan is.
Caroline’s studying in her empty dorm (hon, just compel yourself good grades!) when Stefan shows up. He throws a vervain grenade at her, then breaks a slat on a staircase to give himself a stake. He tells her this is how vampires are supposed to act – they hurt people. He urges Caroline to give in and let go, promising that she’ll enjoy it. Caroline says she won’t let him ruin her life, so he tells her he’ll end it instead. But before he can, Caroline bites him, grabs the stake, and uses it on him.
While Bonnie does a locator spell to find the ascendant, Kai tells her that he came along because he feels guilty. He needs one more chance to prove himself. When she ignores him, he gets frustrated, yelling and grabbing her hand. That just proves that he hasn’t really changed. Back in the house, Elena and Damon explain their plan to Lily. She agrees to go with them to see Stefan, but she has just one condition: Her “traveling companions” get to come, too. It turns out Lily isn’t the only person in her prison world. There are a handful of other vampires there, all desiccated.
Alaric and Enzo bicker as they head to the dorm to capture Stefan and Caroline. Alaric doesn’t get why Enzo wants Stefan to get his humanity back – he hates Stefan. Enzo says it’s only fun to ruin someone’s life if they care. Basically, he wants Stefan to turn his emotions back on so he’ll hate Enzo. “Games are more fun with two players,” Enzo says. Alaric thinks he should reconsider what’s “fun” after what happened to Sarah. Enzo’s just sad and lonely. Enzo notes that at least he’s not checking milestones off a list until death like Alaric is.
Caroline is dragging Stefan’s unconscious body through the dorm when a field-hockey player comes in unexpectedly. Stefan pulls the stake out of himself and whips it into her abdomen. Caroline starts to heal her, but that violates Stefan’s second lesson in losing control: “No saving strangers.” Caroline heals the player anyway, then fights Stefan off and compels the player to go to her room. She summarizes that letting go includes making bad choices. Stefan hears Enzo and Alaric approaching and zooms Caroline away. A vervain grenade rolls down the stairs and Enzo has to rush Alaric out of the dorm before it explodes.
Lily tells Damon and Elena that her companions saved her from her Ripper self. Well, really, being trapped in the prison world did that, since it forced her to confront the monster she’d become. The other vampires allowed themselves to desiccate so Lily could have all the available blood. She had to learn to control her bloodlust so she could save some blood for them, to eventually wake them. The other vampires made her feel human again.
As Lily goes to get some blood to revive her buddies, Elena tests the depths of their desiccation by moving her finger back and forth in front of a vampire’s eyes. Damon says that not only is his mother a Ripper, she’s a crazy one. Elena thinks she feels responsible for her friends. Damon says it’s like she has a dollhouse full of vampires. Elena spots the ascendant and wonders why Bonnie hasn’t found it yet. He tells her that Bonnie isn’t looking for it.
Outside, Bonnie leads Kai into some snowy woods, lying that the ascendant seems to be nearby. Kai’s surprised that she’s willing to be alone with him if she doesn’t think he’s capable of changing. After all, he could kill her right now. Bonnie replies that maybe deep down there’s a part of her that believes he has a small piece of goodness in him. But she’s not going to risk being wrong. She waits until his back is turned and stabs him. He begs her to stop but she wants him to feel how she felt in the prison world. He tells her again that he’s changed. “So have I,” she replies. She raises the knife to plunge it into him again, but he disappears.
Caroline checks on Enzo and Alaric, who are unconscious but alive. Stefan comments that Damon must be doing something else if he “sent the B team.” Caroline turns one of the guys’ weapons on him so he can’t kill them. If he does, the gang will lock him up again and torture him to flip his switch. Stefan says she’s overthinking things. Doesn’t she want to just kill Alaric and Enzo, and be done with them? Caroline won’t back down, so Stefan does, but only so he can go get the field-hockey player.
He reminds Caroline that he knows all about her ability to control herself – he taught her to do it. He bites the player to demonstrate what Caroline keeps resisting. Caroline says that won’t tempt her, but Stefan knows they’re the same deep down. She can break routine for just a little while. He bites the player again, and Caroline just can’t help herself. She feeds on the player, then tosses her aside so she can make out with Stefan.
Damon tells Lily they’ll have to come back later for her friends, since Bonnie can’t transport everyone back to the real world by herself. Lily doesn’t want to leave without them, so she runs to revive them just as the train back to the real world is supposed to be leaving. Damon breaks the jar holding the only remaining blood in the prison world and says they’re going now. Lily again refuses to leave the others – they’re her family. Damon’s hurt by that, understandably. He tells Lily that Stefan is his family, and if she doesn’t want to come with him now to help his brother, he’ll leave her there to rot.
The two of them join Bonnie and Elena to take the trip home. Kai emerges from the woods in time to see them leaving without him. Bonnie gives him a look that says she doesn’t have the slightest bit of regret.
Enzo goes to see Sarah so he can admit that he was just using her. She was a pawn in a game he’s lost interest in playing. He tells her she’s not just an ordinary person and she deserves better. He uses the name that would have been hers if she hadn’t been adopted, Sarah Salvatore, which piques her interest. Meanwhile, Jo examines Alaric and slams him for putting his life in danger. She needs him alive for the next 18 years to raise their child; then he can “run around with guns and vampires and be an idiot.” Well, then he’s going to have to make some new friends because most of them are vampires.
At Vamp Villa, Damon makes up a bed for Lily, who’s going to have a lot of adjusting to do in the 21st century. She confirms that she visited Stefan the night of her funeral. She had just turned and wanted to see her sons. But when she got close to Stefan, she was tempted to feed on him and ran away to protect her children from herself. She missed them just as much as they missed her. Damon doesn’t betray any emotions about that. Lily tells him she can’t really be herself until they get her friends from the prison world. She’d like to know when they’ll be going back. Damon promises it’ll be soon.
Kai goes looking for food in the prison world but only finds desiccated vampires. One of them got enough blood from Lily’s stash to start reviving, and he grabs Kai by the throat. Aww, I bet Bonnie would have loved to see that.
Elena brought back a picture of Damon and Lily, since she wanted to keep a baby photo of her boyfriend. She liked seeing the side of him who’s someone’s son. Damon insists that Lily’s just a way to get Stefan back. Elena urges him to give Lily some time to be the mother she once was. Looking for the good in someone is never a waste of time. Damon doubts that that’ll be the case with Lily, but Elena notes that they have plenty of time to wait.
They make out, as do Stefan and Caroline, who’ve just had sex in the Super Suite. She admits that his way of living without humanity is much more fun than hers. At Vamp Villa, Damon and Elena are nearing the point where they should find a bed. Bonnie walks in on them in the kitchen, so Elena excuses herself to check in with Alaric. Bonnie thanks Damon for helping her get closure with Kai. He turns on the faucet so they can discuss Lily’s friends without her overhearing. They both agree that they’re not going back to the prison world to get them.
Bonnie announces that she brought Damon something from the 1994 prison world. She was going to give it to him the day before, but then he was a jerk to her. To thank him for his notes about the island, which led to her freedom, she got him a souvenir: the cure. She guessed it was the reason he wanted to go to the island when they were in the prison world. She wants him to have it because Abby’s fine as a vampire, because Caroline will come back to them, and because she knows Damon wants to give it to Elena. If he doesn’t want that anymore, he can decide what to do with it instead. This time around, Damon gets to choose.
Etc.: If I had to choose between having Bonnie’s magic and her way with words, I would choose the latter.
The visual of Stefan’s motorcycle just collapsing when he sits on it is hilarious.
I was able to catch a few of the names on Alaric’s baby-name list: Benjamin, William, Michael (we already have one of those), James, Connor, Aiden (already taken), Jackson (ditto), Ethan (that gets saved for Legacies), Liam (dude, he was just in the last episode), Lucas (that would be nice, since that was Luke’s full name), Jacob, Jayden, Jack, Logan (really, Alaric?), and Ryan. Here’s a tip, Alaric: Spend a little more time thinking about girls’ names.
Enzo and Alaric working together is ridiculous. Writers, just admit you have nothing for Enzo and he shouldn’t have been kept on past season 5.
Annie Wersching (Lily) did a photo shoot with two little kids to get family photos for the house, and you have to see the adorable results.
There has to be some source of blood Lily can think of other than butcher shops.
Part of Stefan and Caroline’s makeout session takes place up against a soda machine, so I guess that’s a Salvatore thing.
A big UGH to Bonnie giving the cure to Damon and letting him decide whether to give it to Elena instead of giving it to Elena herself and letting her decide if she wants it. Come on, Bonnie.
An Eternity of Misery 
