“So, dangerous mission tomorrow. Guess it’s time to, eat, drink and…you know, make merry.” Dean says with a flashy smile.

You, Dean, Sam, Jo, Ellen, and Castiel had planned to kill Lucifer tomorrow in Carthage. Thus referring to tonight as, “the last night on earth”. So now, here Dean was, pulling his “last night on earth” speech to hook up with you. Funny enough, this is the first time he’s ever made a move on you…. and man, did his timing suck.