Behind the bar, Stefan finds a picture of himself from the 1920s, with his arm around Klaus. When he asks about it, Klaus says, "I told you, Stefan, Chicago's a magical place." And he did tell him that earlier. I just didn't think it was worth repeating. Commercial.
Mystic Falls: Liz Forbes is leaving Caroline a voice message about having lunch, when Tyler knocks on the front door of Fortress Forbes. Yay!
I'm on the couch now. I couldn't lie in bed like that and keep writing. It was driving me nuts. I knew you'd want to know. Speaking of nuts, Caroline's father is still torturing his little girl. On a narrative level, I think it's interesting that Caroline's gay father is subjecting her to aversion therapy to condition his daughter to be repulsed by what is now her nature. Some people hate this, others find it offensive. I can see why, but I like the layers. Bill was closeted for a long time. He's out now, and out of his marriage. His daughter has been supportive of him and has expressed that she prefers him to her mother, and yet his perspective on the vampire issue is so narrow, thanks to the way he was raised, that he can't even let himself hear her when she explains that she doesn't hurt people (if we can just conveniently forget about that guy she killed soon after she was turned). So yeah, I like the layers. I like his blind spot. I don't think he's necessarily an evil person. I think he's a desperate one, doing the only thing he thinks he can do to prevent his daughter from being a monster. It's an evil act, but he can't see it, because he doesn't understand what she really is. He only believes the stereotypes about vampires, and of course they're true of some vampires, but we've seen a few on this show who don't kill: Rose, Lexi, Stefan (well, you know, before).
Bill shows Caroline the bag of blood again, and she vamps out again, so he explains he's trying to make her associate her appetite for human blood with pain, so that eventually, she will be able to repress her vampyric nature completely. Caroline cries that that's impossible. "Daddy, you can't change who I am." Bill insists he can and then says, "You remember this feeling." Deaf to Caroline's cries of, "No, no, no," he opens the blinds and poor Caroline begins to sizzle.
Chicago: Damon takes Elena to the apartment Stefan lived in during the 1920s. It looks like he left it a month ago. This is stupid and bad, Show. Why would an apartment remain relatively untouched for 80 to 90 years? Seriously? Damon finds a hidden closet and beckons Elena to come see. She just sees the shelves full of booze and says, "Stefan hid his alcohol. What a monster!" Damon tells her to look harder. When she steps up to the doorway, she sees a huge list of names filling up one of the closet walls. "Are these all his victims?" Damon says, "Still handling it?" Elena: "What were you doing in the 1920s -- paving the way for women's liberation?" Damon: "I was around. Chicago's a big city. Stefan was a cocky Ripper douche, but I could avoid him and still indulge in a few Daisy Buchanans of my own." Elena Ughs at him, and Damon leaves her ALONE IN THE APARTMENT while he goes off to investigate Stefan's old stomping grounds. It seems out of character, to me, for Damon to leave her there when he knows Klaus and Stefan are on the prowl, but then it makes little sense that he brought her to Chicago in the first place, since he's the one that's always telling her it's better if Klaus continues to believe she's dead. He tells Elena to come up with a plan while he's gone. He'll come back once he's found Stefan.