"I'm never trashed." Dean said, downing another shot as he saluted Ruby. He'd insist until the day that he died again that he was Dean Winchester, who was never drunk, or hungover, because liquor was his friend. "Eh, what the hell." It was an indication of just how much alcohol Dean had going through his system that he indicated for the bartender to give them two more shots of whiskey, one for him and one for Ruby.
"What about you, Sammy? Gonna take shots with the big boys?" Ok, so maybe the fact he had bought Ruby a drink didn't mean much in the scheme of things. He still wasn't above making fun of her, even if he wasn't calling her 'bitch' right now.