Yeah, it was gonna be great to get out of the hell hole that was New York for a few days. Things have been pretty much taken the fast lane straight down for a ... while and Dean thought that getting away would be perfect. Plus seeing Sam? Bonus.
He was weary of taking a portkey, but he got over it quickly because he was going to see Sam and help him fix the only woman that was in Dean's life. Used to be. Now he had nothing but chicks surrounding him and while on most days that would be the most awesome thing ever ... let's just say, it wasn't.
He found the place where Sam was staying and he was ... impressed. Nice. Giving a nod to Sam as he came up, he looked around, sticking his hands in the backpockets of his jeans, "Looks like you're makin' out."