- Stefan concocts a plan to get Caroline to turn her humanity back on. Damon wrestles with what he should do with the cure. Enzo seeks answers.
- Stefan's duel in cruelty among 'merely physical' lovers finally brings Caroline to turn her feelings back on, over a destroyed last letter from her late mother Liz, but in grief she refuses further contact. Bonnie is furious to learn that Damon didn't hand Elena the cure but stole the ascendant as reward if mother Lily triggers Stefan back to humanity, which might allow Kai to escape. Enzo shows surprising sympathy when his 'creator' Lily admits she can't suppress her ripper nature. Convinced Damon won't allow her to retrieve her ripper family, she tries to turn Elena against him by telling her he had the cure, but he now proposes to take it together.—KGF Vissers
- Wrestling with whether or not to tell Elena about the cure, Damon brings up their future together and what life would be like if they weren't vampires. Meanwhile, it's all hands on deck when attempts to stop a humanity-free Caroline don't go as planned. Elsewhere, when Bonnie discovers that Damon has betrayed her trust, she takes matters into her own hands, setting off a chain of events that leaves Damon dealing with the fallout. Lastly, after being forced to face his traumatic past, Enzo sets out for answers and is surprised when he learns the truth about the day he was turned into a vampire. Stefan, Matt and Alaric also appear.—snowflakeaudrey
- Stefan takes Caroline to a B & B for a break, telling her his mom was full of lies. It's part of his plan to convince Caroline his humanity is still off, then torture her until she breaks.
He calls for towels, planning to eat whoever brings them.
Going over the plan with Damon and Elena beforehand, Damon is delighted to tell Elena that Stefan and Caroline slept together. They plan to drain Caroline and make her weak, then overwhelm her emotions. Elena has a letter from Caroline's mom that arrived after Caroline flipped her switch.
Damon arrives with the towels and shoots Caroline with vervane darts, then Stefan to stage the scene. When they wake up, Stefan tells Caroline they got caught. Their room has been vampire-proofed.
Damon drops by Bonnie and breaks the news about leading his mom on about returning to the prison world. Bonnie isn't happy to learn Lily might be her problem soon. She also can't believe Damon hasn't told Elena about the cure yet.
Elena drops by Stefan and Caroline locked in their room. She gives Caroline the letter from her mom, but Caroline insists Stefan burn it. He goes along to preserve the illusion that his humanity is still off. Elena is horrified.
When Lily shows up at the Mystic Grill, Matt calls Bonnie. Enzo drops in to talk to Lily, his maker. She's happy to see him but he isn't feeling warm fuzzies. Nevertheless, he agrees to join her for a drink.
Back with Damon, Elena is reeling from the fact Caroline burned the letter from her mom. Damon asks Elena where she'd be in five years if she was human. In a loft in Tribeca, with Damon owning a bar and Elena working in the surgical residency program. She wants two kids.
From upstairs, Caroline gets annoyed eavesdropping and decides to distract herself by kissing Stefan. Damon interrupts with crime scene reports of all Caroline's kills, asking Caroline what her mom would think of it.
Caroline turns on them and asks Damon what it feels like to not be able to give Elena the life she wants.
Back at the Grill, Lily tells Enzo that the night she turned him, she and her friends were captured by the Gemini coven. She realizes he thought she abandoned him and assures him her ripper days are behind her.
She tells him about her six friends still in the prison world and that Bonnie has offered to help get them out. Enzo and Lily head back to the Salvatore house, as Enzo is smugly telling Lily that she shouldn't believe what Damon said about getting her friends back. Bonnie finds the ascendant and takes it before they return.
Enzo tries to explain to Lily that her real family is Damon and Stefan, but she thinks the six friends in the prison world are the family who keep her from returning to her ripper days.
With Damon, he prods Elena into admitting she will never be 100 percent OK with being a vampire, but she's OK with that if it means spending eternity with Damon. They're interrupted when Lily calls to demand Damon return the ascendant. She found the cure and threatens to destroy it if he doesn't.
Back in their room, Caroline figures out that Stefan turned his humanity back on when he won't return her advances. She snaps his neck and kicks the door down.
Damon finds Bonnie in the dorm at Whitmore about to destroy the ascendant. He tells her his mom has the cure, but Bonnie doesn't want to risk her life by letting the heretics out. Bonnie says if he wanted to give Elena the cure, he would have by now. She dares him to take the ascendant, knowing it could mean a life without Elena. He walks away.
Out on the road, Caroline gets pulled over -- by her mother. Liz lectures her about killing but Caroline realizes it's not real. She wakes up back in the room with Stefan putting visions in her head and calmly urging her to let the emotions in. Caroline appears to listen to him, but then uses a window shutter to stab him. He grabs her and begs her to stop.
She sees a memory of him going to Liz for a sewing kit to repair Caroline's teddy bear after they dug it up in the woods. Liz bluntly tells him she hopes he and Caroline end up together, but he says he doesn't want to start something when Caroline is grieving. He assures Liz he can be patient. Liz is finishing writing her letter for Caroline.
Back in the room, Caroline is affected by the memory and wants to see more. She asks to see the letter, but Stefan points out it's the one she burned. Caroline starts crying and everything she's done comes back to her. She breaks down.
Damon goes to see his mother. She tosses the cure box in the fire when he says he didn't bring the ascendant, saying she's doing him a favor.
Meanwhile, Elena finds a rose petal and candle spread on the table -- and a ring box. But it doesn't have a ring inside, it has the cure. Lily tells Damon the last thing she wants is for him to get to spend eternity with Elena. She tells Elena that Damon was never going to give her the cure.
Back at the bed and breakfast, Jo tends to Caroline. Stefan thinks Caroline doesn't want to see him, but Jo urges him to check on her. Caroline is beating herself up for everything she's done and isn't ready to talk.
Enzo arrives to meet Lily in the middle of the night, now feeling appreciative that Lily saved him in 1903. She tells Enzo about accidentally walking in front of a car and not being able to resist tearing the driver's head off. His car is a bloody mess. "What have I done?" Lily sobs.
Back at the Salvatore house, Elena realizes what Damon was getting at asking about her thoughts for five years from now. He confesses to Elena that he didn't stop his mother when she threatened to destroy the cure because he's a "selfish idiot" who doesn't want to lose her. Elena suggests they give it to someone else, but Damon tells Elena she's going to take it -- and so will he.
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