" uh huh. i know. i'm not lookin' to start any big conversation. just somethin' you ought'a know. and i'm not gonna let you make me feel weird 'bout telling you i care about you. — now, you gonna watch old movies with me, or what? "
That has always been an issue. Feelings of any kind, no matter how reciprocated they might be, falling flat because Dean feels obligated. He doesn’t say ‘I love you’ the last time he said that was to his mother right before she died. It’s just not- he doesn’t- it’s not what he does. Life and death situations? With Sam? Maybe. That can be decided on a case by case basis but just in general? No.
And because his experience has always been ‘I say it now you have to say it back’ he expected the same from Benny. What he gets is astronomically different. This isn’t baiting. Dean knows Benny and that just wasn’t his style. None of this really was. How like him to just get it off his chest and move on. He’d done the same with Castiel back in purgatory hadn’t he? Vetting him as to why the angel left Dean in the first place, totally unprompted. Then he wanted an answer but there hadn’t been anything leading to it. It seemed to Dean that Benny does what he wants and a man like that doesn’t expect an answer to a big thing like this.
“You gonna talk through the whole thing or actually let me watch? I want to watch Streetcar again, I like the bit about the shoes.” And while he might not say anything Dean’s body language speaks for itself. He’s closer. His heart rate has evened out. Cheeks a bit flushed. He’s comfortable. Relaxed. And yeah, sure, maybe he’s in love.