It's funny; there's these long stretches of being on the same page, and then something sneaks up and reminds him that there's still this huge gulf between his world and his despite the fact they're supposedly both part of 'the hunting community' – stupid things like having homework (and he'll conveniently be ignoring that the same gulf is opening up beneath his feet, with Sam on the other side, the more he thinks about that....). He'd scraped the GED – mostly on John's insistence; as far as he was concerned he could drive, and shoot, and so what more did he need to know to hunt? - in North Carolina (because it only costs $7.50 there, cheap enough to retake the friggin' science paper enough times that getting coaching from Sammy stopped being embarrassing), but schools and formal classes and homework are a different beast entirely, and he can't help but be grateful it's not one he has to tangle with.
It also drives home how young she is – or else just makes him feel really old, whatever - but that's another matter.
> Like, the guy who sang the macarena, is he dead? Because you can't tell me you wouldn't salt and burn him with a smile
“That Alaska chick? Don't think so” - he immediately cringes, because admitting he knows something random like that is pretty shaming for someone who prides himself on his musical taste, but hey; it's amazing what you pick up watching shitty quiz shows in motel rooms (who said TV wasn't educational?) - “Probably not human either though.”
> Might be worth it even without the hunt
“I like the way you think” he grins, though the smirk turns into a little frown as she talks about sloppy hunters and having to ring and ask for bail (Dean being merrily ignorant of the number of times Bobby's had to do the same for John). He's pretty sure he'd die of shame if he ever got caught out like that, because it's the mark of a good hunter that you don't get into trouble, and maybe that's why Dad's kept them out of this little circle – they're good people, probably, and well-meaning, but not really hunters, not in the same way the Winchester boys are.
> ... probably make their heads explode
That makes him snicker again - “That's one escape plan.”