You’re not like the other guys in town, are you?
OH MY GOD, y’all.
You see that thing Dean is doing with his lip in the last gif?
That is a sign of disgust.
Suzy asks him if he’s a bad boy, and he says yes. And it may sound like he’s flirting, but does that look like Dean’s flirting face to you?
He’s disgusted with himself.
He’s just talked about how empty and unsatisfying this kind of sexual encounter is. And she asks him that question, and he thinks about all the times he’s had to lie and lie and lie and LIE to Sam, how he’s had to turn Cas out of a place where he’d be safe (and with Dean) with only lies for explanations, he thinks about how hurt Cas was, and how he’s kept the bad news about the angels from Cas.
He had a chance at something that would have lasted, but he threw it away because he can’t lose Sammy, and hey, that’s nothing new, but this time it feels different.
He’s fucked everything up so badly, and there’s no way he’s not going to lose either Sam or Cas or both when this all hits the fan.
And this just keeps happening, it’s the Winchester merry-go-round, and he is never going to have someone who’ll be there for more than a night, someone to wake up next to every morning, he’s only ever going to have these encounters that feel great for a few hours but ultimately leave him empty and longing for something real and permanent.
Because he doesn’t deserve anything better.
What I find most heartbreaking about this gifset is that they both feel the need to act it out. People are upset about the cheesy language, but was the point. This is not Dean and Suzie; these are two characters in a Casa Erotica reenactment, cause neither one of them can do this without role playing. Which does fit the seasonal theme (And that is about as positive as I can spin this scene)