Stefan brings Caroline to a B&B in Grove Hill, which she thinks is a strange location for him to complain about Lily trying to get him to turn his humanity back on. He says they need a break. This is, of course, all part of a plan cooked up by the gang. In flashback, Stefan tells Damon and Elena that he’s going to pretend he still has his humanity off, then torture Caroline until she breaks. Elena reminds the guys that the last time Caroline thought they were interfering with her one-year-without-humanity plan, she started killing people. Stefan says it won’t be a problem.
In the B&B, Stefan calls the front desk for towels, which is his version of having room service delivered. Damon thinks Stefan will be able to pull this off but Elena is skeptical that Caroline will even want to see him again. Damon implies that she will because she’ll want to sleep with him again. Elena doesn’t want to think about the fact that Stefan and Caroline had sex already. Stefan doesn’t love the way things happened and asks them to drop the subject.
He wants to drain Caroline’s blood to make her weak, then bombard her with memories of things she used to care about. There will be a special emphasis on Liz. She sent Caroline a letter that arrived after Liz died, and Elena thinks it could be the thing that gets Caroline to flip her switch.
Someone knocks on Stefan and Caroline’s door, and she opens it expecting towels (and the easy meal delivering the towels). Instead, it’s Damon. He shoots her with vervain darts, then confirms that Stefan wants the same treatment. He wants this to look realistic, so Damon shoots him, too. Three days later, Stefan and Caroline wake up weak and drained. She asks him what happened and he replies, “We got caught.”
Damon takes Bonnie some coffee at Whitmore, because they’re friends now and he loooooves her. She says that Elena told her that the gang found Caroline, but she didn’t mention anything about the cure. Damon hasn’t told her about it yet; he’s been busying dealing with Lily and getting the B&B ready for Stefan and Caroline. Bonnie notes that he had time to bring her coffee.
Damon says there’s a comet passing by soon that Lily thinks can be used to travel to the 1903 prison world. Though he and Bonnie agreed not to let her to back, he admits that he gave Lily the ascendant. Bonnie reminds Damon of how dangerous the Heretics are and how important it is not to unleash them in the real world. He says it doesn’t matter, since Lily can’t get them back without Bonnie. They just need to stall her and dodge her calls, like she’s a bill collector. Bonnie’s like, “They don’t just stop calling you if you don’t pay your bills.” She tells him not to come to her pretending he cares again.
The gang has been taking turns keeping an eye on Stefan and Caroline at the B&B, and during Jo and Alaric’s turn, they discuss wedding plans. Conveniently, they’re thinking about getting married at the B&B. Elena catches them making out when she comes to relieve them. Jo and Alaric run to the honeymoon suite to see if they might want to spend their wedding night there. Thanks for making an appearance in this episode, guys! You’re really contributing a lot!
Caroline is very unhappy to be trapped in a room with bars on the windows. Stefan cautions her not to drink any alcohol, since they’re already drying out and on their way to desiccation. She ignores him. Elena comes by their room and Caroline guesses that this was all her idea. She reminds Elena of how she attacked Bonnie after she turned off her humanity because Jeremy died. She also killed a waitress for no reason. Caroline doesn’t think Elena has any room to judge her for how she’s handling her mother’s death. Elena says she’s not there to preach. She just wants to give Caroline the letter Liz wrote her.
Caroline verifies that the handwriting is Liz’s, and just looking at it makes her come close to feeling something. She pushes it away, knowing this is exactly what the gang wants. She tells Stefan to burn the letter. He wants to read it first, in case Caroline flips her switch later and regrets not reading her mother’s last words to her. She lights a match for him and Stefan reluctantly lets her burn the letter.
Matt’s back at work after his latest vampire-related injury, and he calls Bonnie to let her know that Lily’s at the Grill, since Bonnie’s supposed to meet her there. Bonnie’s currently at Vamp Villa, looking for something. (Insert obligatory joke here about how she should look in the soap bowl in the bathroom.) She asks Matt to tell Lily she’s running late and stall her. Enzo handles that for Matt, since he’s come by to see Lily. She recognizes him, first from his visit to Vamp Villa and then from 1903.
Damon joins Elena at the B&B, where she’s disappointed that Caroline burned what Elena thought was a slam dunk to get her to flip her switch. “The fact that you suck at torturing people is nothing to be ashamed of,” Damon tells her. She says that at least Jo and Alaric crossed a honeymoon possibility off their list (they don’t want to travel since Jo’s pregnant). Damon asks Elena if she has her own list. She doesn’t, but if she did, the B&B wouldn’t be on it. The “extreme floral patterns” are a deal-breaker.
Since they’ve never really talked about the future, he suggests that they do it now: Where would Elena want to be in five years, if she were human? She says they’d live in a loft in Tribeca, above the bar where Damon works. “You made me Matt Donovan in your fantasy?” he asks. Elena decides he can own the bar. She’s a surgical resident and they’ll eventually have two kids. When Elena asks Damon what he would want in their future, Caroline yells from her room that they’re torturing her. Heh.
Stefan tells her that eventually someone will make a mistake, and he and Caroline can eat whoever they can sink their teeth into first. She decides to distract herself by making out with him, but he’s hesitant to take things too far. Damon and Elena inadvertently save him (or maybe purposely; who knows?) by bringing by a folder full of crime-scene photos from Caroline’s recent adventures. Damon notes that it’s a good thing Liz doesn’t have to come up with ways to cover up her daughter’s murders. She’d probably wonder where she went wrong as a mother.
Caroline taunts that she should be more like Damon and Elena, pretending that she has a future with a normal job and a family. She knows Elena would struggle as a surgeon, since she’d want to feed on her patients. Caroline asks how Damon feels knowing he can’t give Elena the life she wants. She knows Elena doesn’t want to be a vampire. She’ll always be settling. Elena can’t stand hearing any more from her.
Lily’s trip to the Grill is her first time ever in a restaurant. Enzo doesn’t believe her when she says she was imprisoned for 100+ years. Is that her excuse for not coming back for him after she turned him? Lily tells him that she and her friends were captured by the Gemini coven that same night. She promises that she didn’t purposely abandon him – she would never do that. (Yeah, her real kids, sure, but not Enzo!) Enzo seems a little overwhelmed to hear that.
Lily asks him not to talk about her past misdeeds, such as killing a ship full of people. He notes that it gives her something in common with Stefan. From the look on her face, he guesses that her reunion with her sons hasn’t gone well. She blames her time with the Heretics – she transferred her maternal instincts to them. Enzo thinks everything she had to do for them, like rationing blood, was a chore. “Loyalty is never a chore, Lorenzo,” she replies. She invites him to keep chatting, since it doesn’t look like Bonnie’s going to make it for lunch. She says Bonnie offered to get the Heretics back from 1903.
Matt changes clothes in the bathroom, examining his most recent scar and dealing with the pain he wouldn’t let Elena heal. He calls Bonnie to tell her that Lily and Enzo left the Grill while he wasn’t looking. Bonnie’s still searching Vamp Villa, and as Lily and Enzo arrive, she finds what she’s been looking for: the 1903 ascendant. Lily immediately notices that it’s gone, along with the only way to get back her family. She tells Enzo that the Heretics are the only people keeping her from turning into the Ripper she used to be, the monster who killed everyone on the ship. Enzo reminds her that she’s with her real family now, but that doesn’t help. She angrily kicks him out.
Back at the B&B, Elena assures Damon that she’s not settling for a life with him. He tries to confirm that she wants to be human again, but she knows they couldn’t be together if she were. He wants her to admit what she really wants. Elena tells him she’ll never be 100 percent okay with being a vampire, but she can accept it if it means spending eternity with him. Why isn’t that good enough for him?
Lily calls to ask Damon where the ascendant is. She either doesn’t believe him or doesn’t care when he says he doesn’t have it and has more pressing things to deal with right now. She orders him to find it or she’ll destroy something that’s as important to him as the ascendant is to her: the cure.
Caroline notes that Stefan didn’t speak up when she was taunting Elena. She even wondered if he felt sorry for her. He says he just couldn’t get a word in while she was talking. She’s hot, so she starts undressing, then offers to help Stefan do the same. He resists, which surprises her. She can hear his heart and knows it’s racing. Is he nervous? She tries to kiss him but he resists again. That’s all it takes for her to figure out that he turned his humanity back on.
Stefan tries to play innocent but Caroline knows better. He must be in on the gang’s plan to torture her. She tries to entice him to “take advantage” of her. He must be putting her off because he doesn’t want to ruin a relationship they don’t even have. As revenge for lying to her, she snaps his neck. Despite being weak, Caroline kicks the door to the room off its hinges and strolls out.
Bonnie starts a spell in the Super Suite to destroy the ascendant. Damon catches her, and when she says she’s protecting herself, he says she’s free to but not like this. He promises that when they use it to get the Heretics out of 1903, Kai won’t come with them. Bonnie tells him this isn’t about Kai anymore. The Heretics are a lot worse than Kai and a long stronger than the gang. They’d have a field day with Elena once she takes the cure.
Damon tells her that Lily stole the cure and will destroy it if he doesn’t give her the ascendant. Bonnie thinks it’s fitting that his mom is pulling this on him. She continues the spell, lighting fire to the ring of salt surrounding the ascendant. Damon attacks her, yelling for her to stop, but she shoves him off. She points out that giving him the ascendant would risk her life once again. He warns her not to fight him on this.
She asks if he really wants Elena to take the cure. She would grow old without him. If he wanted that for her, he would have given her the cure already. Bonnie spent 24 hours a day with him for four months with Damon and has never seen him this scared. She knows it’s not of what happens if Elena doesn’t get the cure – it’s of what happens if she does. She offers him the ascendant and tells him he’s free to release Kai and the Heretics so they can come after her. Then he can spend the next 70 years watching the love of his life grow old and die. If that’s what he wants, he can have it. Instead, Damon leaves empty-handed.
Caroline is heading to Mystic Falls when she’s pulled over for speeding. She’s pleased to have a chance to grab a convenient meal. But she’s shocked when the cop who comes to her window is Liz. She starts to arrest Caroline for the murders she’s recently committed. Caroline reminds Liz who she is, but Liz says her daughter is kind and compassionate. Liz raised her to be a good person, and Caroline knows how hurt Liz would be to see her like this. Caroline guesses that this is Stefan messing with her head and says it won’t work since Liz is dead.
She wakes up back in the B&B, where Stefan thinks she’s close to flipping her switch. He asks her to take his hand so he can show her something. She breaks the slats on the window shutters and threatens to stake him. When Stefan asks her again to take his hand, she backs down and does so. Then she stakes him and says she doesn’t want his help – she just wants him to die.
As Caroline shoves the stake deeper in and Stefan begs her to stop, he remembers one of the last times he saw Liz. He went to her for a sewing kit that Caroline could use to sew up Miss Cuddles. He shows this memory to Caroline, making her watch as Liz tells him she hopes he and Caroline will get together one day. Stefan says the time isn’t right – if he was going to start something with Caroline, he would want it to be perfect, not in the midst of a time of loss. Liz notes that he might have to wait a while. “I’m a patient guy,” he assures her. He offers to mail the letter she wrote Caroline, but she’s still working on it. She wants it to be perfect, too.
Caroline pulls the stake out of Stefan just as he’s starting to desiccate. She demands that he let her see the rest of the memory. He does, but it’s just Liz watching Stefan leave. Caroline runs to the door and asks Liz to come outside so they can talk. She starts crying, saying she wants to read the letter. Liz can’t hear her, and she leaves Caroline crying at the window.
Caroline orders Stefan to make Liz come back. She wants to see the memory again and find out what’s in the letter. Stefan says he already gave her the letter. Caroline realizes it’s gone and wonders what was in it. She cries as she thinks about all the horrible things she’s done. “I ruined everything,” she laments.
Damon gets home as Lily is preparing to burn the box he’s been keeping the cure in. He tells her he doesn’t have the ascendant, so he’s ready for his punishment. She throws the box in the fireplace and says Damon should thank her. Now Elena will never leave him. As Elena heads into the kitchen, which is filled with candles and flower petals, Lily tells Damon that he made the choice for her. “As long as you’re happy, she never needs to know,” Lily says.
In the kitchen, Elena finds a box that she can reasonably assume contains an engagement ring. Lily tells Damon that she’s not going to give him what he wants, since her intention was to punish him. She uses a poker to push the lid off the box. It’s empty. Elena comes in holding the ring box, which doesn’t hold a ring – it holds the cure. Lily says she left it for Elena to find since Damon was never going to offer it to her.
Jo tends to Caroline while Stefan drinks a blood bag, then tells Alaric he’s going home for a shower and a more intoxicating drink. He’s going to keep his distance from Caroline since he doubts she wants to see him. Alaric knows she’s struggling with her emotions and could use support, but Stefan is sure she doesn’t want it from him. Jo tells him to let Caroline decide that.
Caroline looks through the file of crime-scene photos, then the ashes left from the burned letter. She assures Stefan that she’s not going to flip her switch again. Though she can’t get the words out, she makes it clear that right now, whatever relationship they have or were about to have is on hold.
Enzo meets up with Lily, who summoned him to meet her on a street. He tells her that his family abandoned him and she took him in. Loyalty is important to him, as it is to Lily. She says that cars are so quiet now that you don’t always notice them coming. She reveals that she accidentally walked in front of a car, and when she approached the driver to apologize, she couldn’t stop herself from feeding on him. It erased her pain and loneliness. Unfortunately, it also triggered her Ripper side. “What have I done?” she asks in despair as Enzo comforts her.
Back at Vamp Villa, Elena realizes that Damon’s questions about their future weren’t hypothetical. She knows that taking the cure would change everything. He tells her that Lily threatened to destroy it and he didn’t stop her. Elena’s five-years-from-now fantasy scared him. While all he sees in five years is her, she sees her whole future. He wants her to have everything she’s dreamed of having. He knows he was selfish for not telling her about the cure.
Elena says the situation is complicated. They’ll give it to someone else. Damon firmly says that Elena is going to take it…and he’ll take it with her. He doesn’t want to face the future without her, so if she wants to be human again, he will, too.
Etc.: I can’t believe no one thought to take off Stefan and Caroline’s daylight rings when they locked them up. At least have a last line of defense if they manage to escape. That’s an amateur mistake; the gang should be experts at this kind of stuff by now.
How long have Damon and Elena been back together – like, a couple months? And she’s already back to wanting to spend eternity with him? Really?
Way to keep a constant guard outside Stefan and Caroline’s room, guys. Also, Jo and Alaric wouldn’t be able to do anything if Caroline got out.
We never find out what Liz’s letter said. I don’t think it matters. I think Caroline knows everything her mother wanted to say.
An Eternity of Misery 