Warning: Spoiler Alert
I have a feeling that this would be one of the episodes that Kieren would have insisted that I talk about, since there was so much huge stuff happening when it comes to learning about the Winchester side of the family.
The first thing that should probably gotten out of the way is the continuity that hasn't exactly been followed. Yes, there was the part when Dean first met John in the past, and someone told him to say hello to his old man for him ... but if Henry disappeared when John was a small child, there would be no way for him to say hello for anyone. Unless, perhaps the person was talking about a step-father, or a foster father. But then, there's also the fact that there should be two whole missing years that we're dealing with when it comes to continuity (one from between seasons five and six, and one from seasons seven and eight). So, when Henry looked at the tags that where on the Impala, they should have read 2015, and not 2013 (especially when kind of a big deal had been made at the beginning of seasons six and eight that a year had passed). Boo, writers.
But beside that ... it was good to finally get at least a little bit of information about the Winchester side of the family (after being able to get some about the Campbell side ... even if some of those threads about the family that were picked up in season six were just dropped without the writers giving any real closure). I want to know some more about what this whole thing about being a "Man of Letters" entails. Henry kept repeating that he had no choice about being a member (cuz he was ... what was the term he kept using? ... a "legacy"), but why? With the hunters (from what we've seen so far), it does look like it kind of sticks with families (and there are people who are from "hunting families" who become hunters themselves), but that doesn't mean that there aren't those who don't "get out". So, why does being a "Man of Letters" mean that you have no choice about whether or not you are able to be something other than that?
And I'm not fully convinced that the reason that Cupid was ordered to make John and Mary fall in love was so that a family of hunters and a family of "letters" could have children together, and they could subsequently have both brains and brawn. I feel like there is so much more there than what we are aware of ... so much more than just that they needed the brains and the brawn. Maybe it's just that I want there to be more than just that they needed a family of hunters and a family of "letters" so that they could be vessels, or so that they could possibly stop the apocalypse. Part of it (I'm sure) is that it still bothers me that they haven't explained what it is that makes someone so different that they are able to be the vessel of an angel, and what makes the people within the Winchester line so special that they are able to be the vessels of archangels. I kept talking to the screen during the is episode, and kept wanting Henry to say that they were actually the descendants of angels, and that was why he had no choice about being a Man of Letters ... like he had to learn all of this very specific magic, and at a certain point, he would learn about his heredity ... and that perhaps the organization that he was a part of was created by an angel before they all went back into Heaven so that there would still be someone looking after humanity and protecting it from the demons that would still be roaming around.
I am also very suspicious about the fact that Abaddon is supposedly the last Knight of Hell. They made kind of too big of a deal about it for me to think that we aren't going to see another one at some point ... and why do I want to say that the big reveal that we're going to find out toward the end of the season (or at least one of them) is that Naomi is one? Yeah, I'm still very suspicious about her, but at lot of that has to do with the fact that she's up to no good.