Most Awkward Winchester Family Moment
"Of Grave Importance"
I can honestly say, when you're waiting around for your lunch date to appear, perhaps that's not the best time to start talking about past encounters with the woman. Physical encounters, that is. Especially when it was mentioned first that she slept with your father figure. At least Sam had the "I was soulless" cop out. Just imagine what would have happened if Annie actually showed! Her death got her out of some explaining to do.