In progress. In alphabetical order by first name because the mun is an anal freak.
ASELLUS
[ALLY/FRIEND/WOULD TAP]
Asellus is that chick that Dean gets both unbearably goofy around and can be serious business with in a heartbeat, and he couldn't tell you why that is. Part of it is because he wants to tap it. Hard. He's never made it with a green-haired chick, and she's fun to pal around with, besides. And she owns a bar. It doesn't get much more perfect than that. She might have more shame than him, but it's not much, and he likes that. Besides, she recognizes the Impala for the beautiful lady she is, and that sealed their friendship right there.
So, tl;dr: Dean has the hots for her, but she's a bro on the side.
CASTIEL
[ALLY/BRO/WOULD NOT TAP]
Cas is a bro, plain and simple. While they got off to a...Rocky start, he's pulled Dean's ass out of more cracks than he can count, and while he doesn't say it often, he's grateful. He's hilarious at drinking parties, hard to feed, and sometimes that...Pompous thorn in Dean's side (and he doesn't get Dean's jokes, which is a bummer), but he's got Dean's back, and that's enough. It only gets better with the fact that Cas has a rivalry going with an eight-year-old girl.
TL;DR: Cas is Dean's best friend outside of Sam, and he'd trust him with just about anything at this point.
CLARE
[ALLY/CAS'S WOMAN/PROBABLY WOULD NOT TAP]
She's nice to him, and a damn good hunter, even though she insists on lugging around that huge damn sword. He, amazingly, doesn't see her sexually, but mostly because he's got her all picked out for Cas. And she just gives off...Vibes, and he's slightly put off by them, for all the joking he does. And he thinks she and Cas line-facing is hilarious. Because he's easily amused. He thinks she's a little gullible, compared to Galatea, and so it inspires a little bit of protective instinct toward her, but he figures she'd get huffy if he tried to do anything about it, considering he's human and she's...Not. Amazingly, that fact doesn't bother him a bit. They share a job, and he kind of gets it after Sam's entire ordeal.
TL;DR: She's a good kid, and he thinks she and Cas are perfect for each other.