Sam offered Dean a small nod, acknowledging that he wasn't going to push him any further on what had happened. He wasn't a complete asshole, he knew Dean and he knew he'd take something like that to bed with him. His bed was already full and full of liquor, he didn't need to add a figment of his head and his issue to it. Being without a soul had cleared him, made him unable to feel the guilt of the world anymore, and more, but at least he was learning. If in his world Dean had understood that and was patient with him, maybe he could have stayed this way. But he already knew how that ended.
"Yeah, forty's the new twenty, jerk," Sam's lips twitched up in a smile as he took another drink from his beer. "So see? We're still badass in the future. Well, your present. It's hard, a lot of stuff is - maybe our brand is a little harder - but, we're hunters. We knew we might not live past our twenties and have to give up a chance at normal when we signed up. I'd say we do pretty good, you know, from a kind of outsiders point of view."
When Dean moved to sit in the chair, Sam moved to the foot of the bed and sat on the edge. He drank from his bottle and listened as Dean talked. "And... okay, so, the Jo that was here before, you almost - almost were a thing? But she left and now that she's back, it's confusing you? So... take a chance. A little bit of what makes you happy for a short amount of time is better than none at all. I mean, honestly, no one knows what's going to happen tomorrow, or even five minutes from now, and that goes for anyone, anywhere, not just here. You just have to go for what makes you happy, or makes feel grounded." Sam paused. "But I know you won't listen to me about stuff like that, you have a hard head and I have a bad track record."