Katherine calls Damon to taunt him and get an update. He assumes that she's trailing Stefan and Klaus. Damon climbs into Elena's bed and wakes her up. "You know you were dreaming about me. Explains the drool," he says. She's annoyed but he knows where his brother is and tells her to start packing. They drive off and he hands her Stefan's diary. She refuses to read it and then does so. They go up to one of Stefan's old apartments. In the pantry is a list of people he killed. Damon explains that his brother was 'cocky ripper douche' and he spent most of the 20s avoiding him. She sits around and reads the diary while he takes care of something.
Stefan and Klaus arrive in Chicago. Stefan can't remember much of his time there. They start recalling his days during prohibition, having sex in cars and eating people. In a flashback, Stefan goes into a speakeasy. A blond licks what's left of his date off his face. He's intrigued. They keep trading barbs. Her name is Rebecca. Back in the present, Klaus tells his minion that they are going to see his witch. Klaus takes him to the old speakeasy to meet Gloria, the witch. She tells him spells have loop holes but ancient spells mean they need to contact ancient witches. She demands that he bring her Rebecca. On the bar, Stefan finds an old photo of he and Klaus in the 20s. This confuses him. Klaus reminds him that he blacked out a lot back then. They didn't get along. They go down to see Rebecca and take the knife out of her heart. She isn't reviving instantly. Stefan flashes back to killing people with Rebecca. Klaus shows up and orders her to come with him. She's his sister. They sit around a table and Klaus gets snarky. Some guy comes in looking for his wife. Stefan begins torturing his wife and then makes the guy drink her blood. Flashback over, Klaus tells him,"I was your number one fan." They leave for his old apartment while Rebecca wakes up.
Damon drops by Gloria's. He chats with her and she says his brother will be back with Klaus later. Meanwhile, Klaus and Stefan walk into his old apartment. Elena hides in the pantry. Klaus opens it so he can see the list of his victims. He doesn't see her but Stefan does. The vampires leave. Damon returns and gives her orders.
Stefan and Klaus recall more of their past. Klaus gives him advice about how to deal with his sister. They drink and Stefan wonders how he became such a 'hybrid dick'. Klaus recalls them being in the club when it was raided by cops using wooden bullets. Klaus compelled Stefan to forget him and his sister as they escaped. Stefan wonders who he's been running from for so long. "Story time is over," Klaus says. Stefan spots his brother and goes out to see him in the alley. He orders Damon to get Elena out of town before Klaus realizes she's alive. She's standing beside them. Damon goes inside and starts trading barbs with Klaus, which leads to the Original nearly tearing his head off. He lifts him up the throat and starts stabbing him with a cocktail umbrella. Before he can kill him, Gloria orders them to take it outside. Klaus tells Damon that Stefan won't want to go back to his other life. Back outside, Elena asks Stefan to come home and hugs him. She's about to stab him with a needle but he grabs her and explains that things can never be the same. His life with her is done and he doesn't want to be with her. He walks away. Damon returns and drives Elena home.
Klaus returns to the warehouse to discover his sister is out of the coffin. She leaps out and stabs him. They flashback to abandoning Stefan. Klaus tried to give her a ultimatum but she chose Stefan. He stabbed her for it. Back in the present, he pulls out the blade and tells her to stop pouting. He calls Stefan in and commands him to remember everything he felt. Rebecca notices her necklace is missing. Stefan looks guilty because he gave it to Elena. He recalls finding it and then being interrogated by a cop looking for the vampire siblings.
Tyler drops by Caroline's looking for her. Over at the crypt, Caroline yells for her daddy. Vervane flows in as her dad enters. He takes her ring off and starts waving blood in her face before opening the window. She burns and screams until he shuts it. He wants to condition her to associate vampirism with pain and starts again. Later, she tells him that she doesn't need to be fixed and she's learned to adapt. He keeps trying to condition her so he won't have to kill her. Once the sun is down, he leaves her in there. When he gets outside, Liz pulls a gun on him. He defends what he's doing out of love for their daughter. She calls Tyler out to free her daughter. He frees Caroline. Her mom takes her home, feeds her and puts her to bed. "Thanks for believing in me," she tells her mom. Liz leaves and Tyler comes in to cuddle with Caroline. She cries that her dad hates her.
Cryptic commentary: I'm really enjoying Stefan's life getting fleshed out like this. It makes him so much more interesting. Rebecca is an intriguing addition and could be a great counter to Elena. She seems designed for it. Thankfully Katherine is also back in the fold now. It was a tight episode that didn't feel rushed for once. Klaus has such a goofy laugh and I loved watching him stab Damon with a cocktail umbrella. Someone should do that every week.