Dean was nearly always immune to such things as hurt looks. He hunted things for a living that were so evil that they made most people run away in terror, so pouting blondes normally didn't mean that much. Jo, though...seeing her look hurt wasn't something that Dean could handle very well.
"Alright." He said hastily, clinking his glass against hers again. "Here's to you beating me even when you're drunk and I'm not, and to my little brother keeping his mouth shut."