This certainly isn't a conversation that Dean wants to have sober so he doesn't begrudge Kara taking the whiskey. He smirks at her. "Give me a little while to figure it out, Sweetheart. I haven't found anything I couldn't take down eventually." Except Lucifer. He could never take down Lucifer, but a part of that has to do with all the time Lucifer spent in Sam's body.

Dean exhales noisily at that. "Maybe? Probably," he admits. "But I can't be talked out of it. One of us ought to get something that resembles a damn happy ending." He's been thinking about what he's going to leave behind when he's gone. He knows it's not going to be a brother because Sam won't ever stop hunting either. Sam is probably going to tell him how much their lives aren't fit for kids, how he can't protect Kara or any children from the things they hunt, but Kara doesn't need his protection and there's a good chance that their child won't either.

"You definitely shouldn't be there. Sam knows you're not sketchy. If you're here, Sam won't say what he really means. He'll save it for when you do leave. Besides, what's he really going to do? Throw a hissy? I'm 38 years old. If I want to have a damn kid, I can have a damn kid."

Sam's probably not going to react well, but Dean doesn't care. He has made up his mind.