When Stefan loses a bet with Caroline over who can scare a human being the fastest, Stefan has to make good on his promise to sing karaoke with Caroline.
Meanwhile, Enzo wants to drop Sarah Salvatore Damon and Stefan's house only to find Lily Salvatore at the doorstep. Is this an apparition, or is Enzo seeing things?
Enzo races away with Sarah, and as Sarah wonders what's going on, Enzo let's her know that Lily was the one who turned him in 1993. Enzo recounts Ripper Lily to Sarah, who listens in horror that Enzo would know so much about her ancestors.
At the Salvatore mansion, Lily questions Damon on when she'll be reunited with her menagerie of plastered undead to which Damon says it has to take a celestial event, a rare one at that.
Over at karaoke central, Caroline sings her heart out, while Stefan watches on sipping on some human blood.
In walks in Matt and Tyler. Seeing Stefan drink from a compelled customer and bar patrons compelled to enjoy Caroline's performance, Matt and Tyler stand frozen in fear of what to do.
As Damon and Lily drive over to meet Elena, Lily relays to her son that she knows about the cure because she accidentally eavesdrop on his conversation with Bonnie. Like mother, like son, Lily knows Damon has not told Elena yet about the cure for fear of being alone.
After Matt and Tyler watch Caroline sing, the blond vampire forces the two to play Caroline trivia. Since both guys have dated Caroline, they should know her enough to survive the game.
However, when Stefan steps into the game, it's only a matter of who dies first. Temperamental Tyler grows to be impatient when Caroline flips a coin to see who dies first. Tyler points a stake at Caroline and begs Matt to leave, but before he can act fast, Caroline acts faster by using Matt as a shield when Tyler stabs Matt. Nice going, Tyler.
When Damon eventually convinces Lily to provide the emotional trigger for Stefan, it's just in time as Matt's bleeding out.
Damon tells Lily what to say to Stefan in a heartfelt speech, but will Stefan return to normal, and in turn trigger Caroline to come back?
Learning that Jo's having a baby isn't easy for Elena, especially since she can't have children of her own, or so she thinks. As much Damon wants to Elena that he has cure for her, he wants to cherish these moments with Elena as much as possible.
Jo, on the other hand, breaks the news to Damon and Elena that the ascendant should be destroyed as quickly as possible now that Kai's dead because Lily was in cahoots with vampire creatures, who could siphon magic off of each other. Vampire witches? Scary.
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