The points for the leap of faith outnumber the stupid points. He needs another chance. Just the one though.
I appreciate what you're trying to do, but just because I'm single now, doesn't mean I need to be with someone else. Ruby is not my first love, but I have spent more time single than I have been with other people. I can cope on my own.
I'm not sure. With angels it gets odd. We tend not to really go there. And, no, you're not Dean's sister, in any way.