Wow guys. I didn't expect to come out of this particular episode overwhelmed with feelings about Dean Winchester and his desire for love, but that shows what I know. "Paint It Black" was a story about two things we've see a lot of this season: vengeance and hope. And also possibly coming to terms with one's latent bisexuality, but we'll get there.
In the underworld secondary plot we had Rowena, a witch who was disgraced and exiled from the vatican of Witches because of her family choices (having a child). She finally gets to confront the head of the grand coven...and learns the object or her revenge dreams are powerless, their secrets stolen by the Men of Letters. She deals with this very well by turning her rival into a hamster and shifting her sights to her son's favorites - the Winchesters. On the other side we had the ghost of a jilted renaissance nun, Isabella who took vengeance on cheating men. She was defeated also by a man of letters, using her own words. Neither of these ladies found release from their cycles of violence, just more anger. Isabella and Rowena both are so lost in revenge, much like Dean can become lost in the Mark of Cain, that their humanity is gone, rendering then nothing but killers. Rowena however is a very dangerous and ambitious killer.
Contrast that with the still human, for now, Dean and his hot nun friend for the episode, Sister Matthias. He expressed some respect for her choice and ability to transform her pain into devotion to something higher, a different kind of life and love. Though Dean has given up being cured, he still has a mission. But he also still wants more. We see this again in the stand-out scene of the episode when Dean, after false confession to cheating to draw out Isabella, confides in the priest that he's not ready to die yet...And also he wants things he's never dreamed of before.
Those few lines were enough to make certain sections of the internet explode and with good reason. What we have here was, for me and for a lot of viewers, a pretty clear admission that there are relationships in Dean's life that he wants to change, to experience in different ways as he said. Given that we've been getting hints at this sort of thing for, well, years; and that we've had Dean suddenly liking cake over pie and the only way we've seen the Mark of Cain be controlled is through romantic love etc...the idea that this confession may be laying the foundation for Dean to maybe be more willing to explore his sexuality isn't too much of a stretch. No matter how you read that confession, whether as opening the door further for an end of season change in Dean's relationship with a certain angel or just Dean confessing finally that he does want to live and find something new to live for, rather than the pedal tot he metal life he's always known it was a powerful moment. Bravo to the writers and Jensen Ackles for such an amazing scene.
What this episode seems to be doing is setting up the final run of the season. It looks like Sam still won't let go of the idea of saving Dean, and perhaps since there's now a connection between the Men of Letters and Witches, he might turn to dark magic to do it. It seems also that Dean, like sister Matthias is going to have to give himself over to some faith and a higher power to release him from his cycle of violence, though I do indeed hope that means Dean confessing to someone (anyone) that he not only wants to live but that he believes he deserves to.
Next week: everyone we love is back as Cas, Metatron and BOBBY return!