Castiel and Kitty
Castiel decided being social was necessary in these sorts of situations. He decided that merely coming to The Musain and just drinking wasn't going to help him become social, he actually had to speak to people.
And that problem was solved when a woman approached him with a smile. "Hello," he offered her in return. "My name is Castiel."
See, Castiel could be... less than awkward sometimes.