We fade back in on the image of the painting the librarian gave the boys while Sam tells Dean about the difference between the paintings. They're back in their Tony Montana motel room. Dean asks if Sam thinks that the dad is trapped in the painting, busy giving out "Colombian neckties like he did with his family?" Ugh, that phrase is too graphic. Though since it is also sometimes expressed as a "Cuban necktie," my Tony Montana obsession is becoming less random as the episode goes on. Sam doesn't understand how Isaiah could be out and about like he is if his bones are dust. Dean thinks they should look at the painting some more to see if anything else changed. Sam asks, "What, like a DaVinci Code deal?" but Dean looks at him blankly: "I'm still waitin' for the movie on that one." Hopefully so that he can hunt down and kill that hairdo Tom Hanks sports in it.
Dean concludes that they need to return to the auction house to look at the painting, and then changes the subject as he flounces on the white-leather-padded headboard. Why does Dean look so comfortable there? Ah, I think we've seen it before, set design. Dean says this turn of events is good because now Sam gets to "crush on [his] girlfriend some more." Sam gets mad at Dean for trying to "pimp" him out to Sarah, and yells some blather about how it doesn't matter if he likes her because he's just going to have to leave and why does Dean care about him hooking up anyhow? Dean's response to the last question is actually very believable: "So maybe you wouldn't be so cranky all the time." Sheesh, seriously. Sam's panties remain in a twist, so Dean decides to tug on them some more, telling his little brother that Sarah could be good for him. Dean then carefully broaches the subject of Jessica, assuring Sam that he doesn't know what it's like to lose someone like that, but suggesting that Jessica would want Sam to be happy. And, if you'll allow me to get blathery for a moment, I do have to say that I think Dean is making an emotionally intelligent argument. Sam looks off into the distance with watery eyes and reluctantly agrees. He says that Dean is right that part of his weirdness is about Jessica, but "not the main part." When Dean asks what the main part is, Sam just sort of looks at him pointedly, and Dean gets that he's talking about their hunt for the Big Bad. Dean leans back onto the headboard and pretend-closes his eyes, telling Sam that no matter what, he has to call Sarah about seeing the painting.