Penny will learn if she stays friends with Dean that he will always say he's doing awesome, even if his version of awesome means bleeding to death and looking at this side of Hell.

Hey, he's got a unique way of looking at things as as someone who's died more times then he wants to count, he thinks he can make light of it in general, particularly when Penny is here and fine albeit City Dead.

"Yeah I'm going with still pretty damn cool. You want another mimosa?"

Yeah, he might get her drunk but he will stick to his word. He'll carry her home, make sure she's safe and not take advantage. Okay, he might kiss her but that's hardly taking advantage if you ask him.