Trama

Damon concocts a risky plan involving Lily to stop Caroline and Stefan from wreaking havoc; Elena re-evaluates her life as a vampire after learning that Jo is pregnant; Sarah turns the tables on Enzo; Tyler and Matt wind up in danger.

With their humanity turned off, Stefan and Caroline begin wreaking havoc at Whitmore, leaving Damon to come up with a risky plan involving Lily. After rushing to help Jo treat victims of Stefan and Caroline's latest killing spree, Elena discovers Jo is pregnant, prompting her to reevaluate her own life as a vampire. Meanwhile, when Sarah boldly turns the tables on an unsuspecting Enzo, he is forced to open up about his tragic past. Lastly, at Scull Bar, a twisted round of karaoke leaves Tyler and Matt in a dangerous situation.—snowflakeaudrey

Caroline and Stefan try to settle a bet by scaring a bartender to death after hours. Caroline compels him into thinking he's having a heart attack, then covered in spiders, until he finally dies. She declares victory and insists they go sing karaoke.

Enzo drags Sarah Salvatore to the boys house to drop her off. But he's unnerved when their mom opens the door. Enzo takes Sarah and runs. Lily was the one who turned Enzo in 1903.

Inside the house, Elena and Damon have a cozy morning with his mom playing house downstairs. When Elena goes to get dressed, Damon has to keep her from seeing the cure in his drawer.

At breakfast, all Lily can talk about it returning to her prison world to get her friends. Elena gets a text from Jo that someone has been killing people at Whitmore.

On the road, Enzo explains the Salvatores to Sarah, then calls Lily the most dreadful person he's ever met.

In 1903, Enzo tries to board a ship from London to New York, but is turned away because he's sick. Lily comes to his rescue.

Enzo explains to Sarah that he died on the voyage. He tries to compel Sarah to forget everything about the Salvatores, but she's on vervane -- from Matt. She jabs Enzo with a needleful.

Back at Whitmore's bar, Caroline sings karaoke to a captive audience of students trying to study. Stefan compels them to listen.

Matt and Tyler drop by in the middle of their police training and are appropriately freaked out. Damon doesn't let them leave.

On the road to Whitmore, Damon tries to prepare his mom to talk to Stefan and bring his humanity back. She overheard Damon and Bonnie talking about the cure. She knows he's afraid he'll lose Elena if he gives it to her.

At the hospital, Elena heals one of Caroline's victims. She breaks the news to Jo that Damon's mom is back and Kai is trapped in a prison world. Elena realizes Jo is pregnant and congratulates her. Elena feels a pang of regret.

Enzo wakes up hogtied on Sarah's couch.

Lily takes Enzo to the ship's doctor. Under compulsion, the doctor says Enzo won't live out the week. She explains to Enzo that she died of consumption.

Back at the Whitmore bar, Caroline leads Matt and Tyler through a round of Caroline trivia about herself to determine who lives. She asks a question that only Stefan knows the answer to, then announces they're going to kill them both.

Back at the hospital, Caroline and Stefan's victims line the halls. Elena sees it as a reminder that there's a part of her that is capable of the same thing. Jo mentions Elena's reaction to her pregnancy news and asks if she's talked to Damon about her feelings. Elena doesn't see the point, since there's nothing to be done about the fact she's a vampire.

In 1903, Lily tells Enzo how she was sent to a sanatorium by her husband and left to die, but it was there she found her "real" family. She invites Enzo to join them, making it sound all warm and fuzzy. As he coughs up blood, she slices open her palm and pours some of her blood into a cup for him.

At Whitmore, Lily worries how she's supposed to connect with Stefan. Damon suggests she tell the story of how she came back to get them -- but Damon realizes she wasn't coming to get them. Lily admits she's been struggling to reconnect with how it felt to be their mother. She explains her "new" family helped her find herself again, but she lost any feelings she had for her old family in the process.

In the bar, Caroline taunts Tyler and Matt as she threatens to kill them. Matt tries to mediate, but Tyler breaks a chair for a stake and tries to charge Caroline. She grabs Matt and puts him in the path of the stake and Tyler ends up stabbing Matt through the gut.

Damon calls Elena, who suggests Lily simply try lying to Stefan.

Damon orders Lily to give it her best shot, but she was assurances that they'll go get her people. She points out he's lying to Elena by not telling her about the cure and he gives her the ascendant as assurance.

Enzo tells Sarah he woke up on the ship at sea, starving for blood and surrounded by corpses. The doctor comes in, compelled by Lily, and slits his own throat as an offering to Enzo. He looked around everywhere for Lily, but she was gone, along with her promises of a new life.

Enzo turns on Sarah and decides to do to her what Lily did to him.

Back at the bar, Stefan and Caroline wonder if Matt dies, does that trigger Tyler's curse again? They're interrupted when Damon and Lily walk in.

Damon gives Tyler his keys to take Matt for help.

Caroline realizes Lily is there to turn Stefan's humanity on, and then he's supposed to turn on hers. So she stakes Stefan in the back and runs.

At the hospital, Matt refuses Elena's blood and insists on a doctor instead.

With Stefan, Lily tells her she's a ripper like him. She pours on the motherly warmth, telling Stefan the story he wants to hear about visiting him the day of her funeral. Damon watches as she reacts the sweet sentiments he fed her earlier. She promises never to leave him again.

It works. He turns his humanity back on and hugs his mother with tears in his eyes. Stefan takes a few moments to contemplate all the killing he's responsible for then resolves to go find Caroline.

Elena checks on Matt, who tells her he can't hate vampires and also use them to his advantage.

With Enzo, Sarah convinces him to let her go.

Elena tells Damon she was jealous when she heard about Jo's pregnancy because she always wanted a family and knows it's never going to happen. Damon asks how she could feel if things could be different, but doesn't elaborate.

They get an urgent call from Jo. She says they have to get the ascendant back from Lily. She explains that long ago Lily met a group of heretic witches who could siphon power like Kai. She turned them, and as vampires they always have power to siphon -- so they're both witches and vampire, and ruthless. They were coming to kill the Gemini coven when the coven stopped them and sent them to the prison world with Lily. "Imagine Kai with the bloodlust of a vampire -- now imagine six of them," Jo says.