Later, an orderly brings Anna her meds, as she sketches a picture of what looks like a stained glass window. When she turns around, she jumps back in horror. When the orderly asks her what's wrong, she says, "Your face! What happened to your face?" His face is all face-like, for the record. He says, "I know, I'm downright kissable," and his eyes turn demonic black. Anna uses telekinesis (which she also can do -- just go with it; she has pretty red hair), to slam him against the wall, knock him out and make her escape. Run Anna, run. The title card flaps its way across the screen on bat-like angel wings.
At a pool hall, Sam is pretending to be drunk, but he's really just hustling some big, burly guy. Go Sammy, go! Good for you, you're spreading your wings. Not that you have any, yet. Or horns, for that matter. Dean plays along, and tries to convince the guy it's not fair to be taking advantage of his drunken brother. Sam, who has already lost "two bills," ups the wager to $500. Dean acts disgusted, while the victim can nearly taste this low hanging fruit. Just when Sam is about to make a killing, Ruby appears at the bar. Sam's face goes from fake-drunk to serious, and he tells his sucker to keep the money. Dean's all, "What?" until he realizes Sam is walking right to Ruby. Then he's all big-brother style mad. As Sam greets her, Dean tells Ruby she's got a lot of nerve showing up anywhere near him. Since she's equally enamored of Dean, she says she just has some information to pass on, and then she'll be gone. She tells the boys about Anna, who seems to be important. Ruby is working off demon whispers that some big-timers have shown up to find Anna, and their orders are to capture her alive. "I just figure that whatever the deal is, you might want to find this girl before the demons do," and Genevieve seems to have mastered varying her facial expressions in this episode. Good job, Gen. Don't let me down. Sam is receptive. Dean is not. Ruby feels she's done her duty, and after bickering back and forth with Dean, she turns to leave. Sam stops her and asks about the hospital Anna is in.
Nighttime: On the road in Metallicar, Sam's on the phone, finagling a copy of Anna's missing person's report. Dean is suspicious and annoyed that they're taking a three day drive based on the word of a demon. He wants to know why Sam trusts Ruby. Sam says, "I told you Dean, she helped me go after Lilith." Dean asks him to expound upon that. Sam gets his bitch on (which you'll see he does more than once in this episode, I'm just saying). "Sure Dean, let's trade stories. You first: how was Hell? Don't spare the details." Sheesh, I don't blame him for feeling hurt that his brother can't confide in him about his trip to the pit, as well as frustrated that that very same brother wants to be all up in his business, but that still seemed a little harsh, didn't it? I mean Dean was in actual Hell.