He knows it, of course he does; enough for it to seem like he's dealt with it himself.
You've only been hunting with them and the others for a few years, but he'd picked up on all of your little things and mannerisms, especially things that could bother you.
So, he knows. He knows about your upbringing, about the things you've been through, and he knows —understands — how sometimes, after a particularly hard hunt, or after seeing something particularly bad, you can't bring yourself to speak. So he doesn't force you, and neither do Sam and Cas, but he just— gets it. He knows how to treat you when you're like this — not with pity or anything of that sort. Just understanding.
And it's not a surprise after this hunt either.
It's bad, the crime scene specifically; it makes your stomach churn despite all you've seen, and it's one of the rare times where you have to step out, go around the corner and breathe.
And while Sam talks to the cops, Dean walks around to you, posture relaxed but eyes already a bit worried, and steps to where you're standing, nudging his knuckles under your chin to make you look up.
“You hurt anywhere?” He asks, gruff but with a certain gentleness that you already know, and his fingers touch your jaw, turning your face around a bit.
And when all you can do is open your mouth and close it again, throat tight, and shake your head, his gaze softens.
“Alright.” He mutters softly, his hand landing on the top of your back to lead you along, closer to the car, but making sure you're facing away from the crime scene. “Sam's almost done, and then we'll get you home, yeah?"