On The Vampire Diaries Season 6 Episode 19, Stefan and Caroline check into a hotel and he pretends his humanity is still off and wants to keep the party going. His plan is to drain her of her blood and torture her into turning her humanity back on. Damon shows up to the hotel to shoot them both with vervain darts in order to keep the ruse alive.
Damon visits Bonnie to bring her coffee. She wonders why he hasn't told Elena about the cure, but all he wants to talk about is Lily and how badly she wants to get her friends out of the prison world. Bonnie isn't happy to learn that Damon gave Lily the Ascendant.
Elena takes over for Jo and Alaric on Caroline and Stefan watch, delivering a letter Liz mailed shortly before she died. Caroline instructs Stefan to burn it and to make her think he's still like her, he does.
Matt works a shift at the Grill and calls Bonnie to tell her that Lily has arrived for lunch. Enzo gets there first and gets an audience with her first.
Elena and Damon discuss what their future would hold if they were human while Caroline kisses Stefan to take her mind off of the fact that she's desiccating. When Damon and Elena go up to deliver another round of humanity torture, Caroline turns the table on Elena and tortures her instead.
Lily tells Enzo that she didn't abandon him; she and her friends, the friends she intended to introduce him to, were captured by the Gemini coven on the night she turned him. She takes him to the house and discovers the Ascendant has been taken.
After the run-in with Caroline, Damon and Elena talk about what she wants out of her life and whether or not she's settling. Lily calls and demands Damon return the Ascendant or she'll crush the cure.
Caroline continues trying to come on to Stefan during their confinement and he continues spurning her advances. She knows his humanity has been back on the whole time and uses the last remaining bits of her strength to break out of their room after snapping Stefan's neck.
Damon finds Bonnie attempting to destroy the Ascendant in her dorm room. He tells her that Lily has the cure and will destroy it unless he returns the Ascendant and she tries to light it on fire. When she offers him the Ascendant, he refuses it.
Caroline gets pulled over for speeding hallucinates her mother when she's pulled over. Sensing it's a trap, Caroline wakes up from a dream put in her mind by Stefan. While she's trying to kill him, he gives her another memory, a real one, and Caroline turns her humanity back on.
Damon tells Lily that he didn't bring her the Ascendant and then she throws the box containing the cure into the fire. Elena enters the kitchen to find a ring box on a table with the cure inside.
Caroline tells Stefan that they can't happen after she pours over the case files of the people she killed. Enzo goes to Lily when she calls and she reveals she killed a driver on the road, becoming the Ripper once more.
Damon and Elena discuss the cure and whether or not she should take it.