Continuing from last week, Caroline and Stefan are still on their no humanity bender. This week they take over a bar allowing Caroline to sing to her hearts content. A guy hears a noise and sees the body of his dead friend. Caroline compels the guy to have a heart attack and Stefan says that’s cheating. She continues to compel him to think there are spiders everywhere and that he can’t breathe and he dies. Since she won he has to do karaoke with her.
Caroline continues singing even after students complain they are trying to study. Matt and Tyler arrive at the bar and find Stefan has compelled everyone to listen. Stefan blocks them from leaving. Caroline says its time to play Caroline trivia. She will ask questions and whoever answers them right gets to live. She asks Tyler when her birthday is and he gets it right. She asks Matt what her favorite color is and he gets it right. Caroline then asks what her mom’s final memory was before she died. They both have no clue, but Stefan says it was teaching Caroline to ride a bike. Since Stefan got it right they both get to die.
Caroline flips a coin to see who dies first, but Tyler slaps the coin out of her hand. Tyler breaks a chair into a stake and goes to stab Caroline, but instead stabs Matt.
Enzo takes Sarah to the Salvatore house to give her back, but Lily answers. Enzo says they are at the wrong house and he grabs Sarah and leaves. He tells her that woman is the one who turned him into a vampire back in 1903.
Enzo tells Sarah he was taking her to her family and explains that Damon was bad and is now good but he killed her parents and Stefan was good but is now bad. He says Lily is the worst he has ever met.
We see human Enzo trying to get onto a ship, but they won’t let him since he is sick. A woman offers to help and takes him to a doctor–it’s Lily. Enzo tries to compel Sarah to forget him, but she tells him Matt gave her some vervain and stabs Enzo instead.
Enzo wakes up to find Sarah and he says she made a mistake. She says her mistake was trusting Enzo. He remembers back when he was at the doctor’s with Lily. The doctor says he can cure Enzo but it is expensive. Lily compels the doctor and he reveals he has saved no one and Enzo will be dead in a week. Enzo says she should leave, but she tells him she already had it and that she didn’t survive.
Enzo is being taken care of by Lily and he asks why she is caring for him. Lily says she was sent to a sanitarium to die. She has found her true family and they are traveling with her. She tells Enzo he can join them and never be alone again. Lily cuts her hand and pours some into a glass and has him drink from it.
Enzo tells Sarah that when he woke up he had such a bad craving for blood. The doctor comes in and says the woman who helped him killed them all and told him to come feed him. Enzo searched for Lily on the boat, but she was gone. He ties Sarah up and checks to see if the vervain is out of her blood. She asks for the choice he never had and that she will never look for the Salvatores. He tells her to have a nice day.
Elena tells Damon that he needs to give his mom a chance like she gave him a chance. Over breakfast, Lily asks if Elena misses being human before bringing up the Ascendant. She says there is a meteor shower in two weeks that could be the celestial event. Elena gets a text from Jo about people wrecking havoc on campus. Elena gets to the campus to help Jo hand out vampire blood. She tells Jo about Lily and that Kai is in the 1903 prison world. Elena realizes Jo is pregnant and hugs her.
Damon drives Lily to the campus and has her text Elena on the way. Lily asks if she should end it with I love you and he says okay. Lily says he must be afraid he will ruin their love if he gives Elena the cure. She can tell he is scared Elena will want the cure and leave him.
Lily and Damon are on campus looking for Stefan. Elena tells him they are at the Skull Bar. Lily asks what if Stefan doesn’t remember her and he says she will. He tells her to channel the feelings she had when she came to get them back in 1903. She looks confused and Damon realizes she wasn’t coming to get them. She says she has been trying since she got back. She has been trying to remember mourning he and Stefan. She says her new family helped her find herself, but her feelings for Damon and Stefan were gone.
Damon calls Elena and tells her about his mom rejecting him. Elena says Stefan doesn’t know the truth. Damon goes to his mom and tells her that she is going to lie her best to get her desiccated family back. He gives her the Ascendant to ensure her best performance.
Tyler tries to save the injured Matt as Damon and Lily show up. Stefan is shocked and he says it is his mother. Damon tells Tyler to get Matt out of there. Stefan says his mom died and this is some attempt by Damon to get his humanity back on. Caroline puts a stake in Stefan’s back and runs off.
Tyler gets Matt to the ER and tells Elena what happened. Matt refuses vampire blood. She asks why and he says he has died so many times, mostly at the hands of his friends. He says she is always one flick of the switch away from being a monster. She asks to make it better. He says he can’t hate vampires and then use them.
Lily pulls the stake out of Stefan’s back. She tells him she’s a ripper and that it’s her fault for his lack of control. She explains that is why she had to leave. She was new to the blood lust and was afraid she was going to hurt them. She says the last time she saw them was the day of her funeral and that he didn’t imagine seeing his Angel. We see Damon telling her exactly what to say before they got to the bar. She says when she had gotten her appetite under control and was coming back for them she got banished by the Gemini. The hope of seeing them again was all that kept her alive there. She touches Stefan’s face and tells him she will never leave him and she’s his Angel. His humanity comes back and he hugs her.
Damon tells Stefan he has one night to do his shame spiral before he has to go get Caroline, but Stefan says he can find her. Damon tells Elena that Stefan is better and after Caroline. Elena says she wants to throw Jo a baby shower. She tells him she didn’t react well and wants to make it up to her. He asks if she is jealous. She says she wanted to have a family, but she also wanted a lifetime with him. He asks if things could be different, but she says they’re not.
She gets a text from Jo. She says her dad wants the Ascendant, but Damon confesses he gave it to Lily already. Jo says they have to get it back. We find out that Lily’s new family are bad witches that are now also witch-vampire hybrids, that syphon magic just like Kai did.