You know, I heard plenty of unflattering things about 10x16, but I rather enjoyed it!
I mean, I think if I didn't have six more episodes to catch up on and I'd been waiting on it a week I'd be less patient with it, because it's pretty MotW and the segments dedicated to the larger mytharc (Rowena's bits) aren't immediately arresting. Like, woo, the Men of Letters fucked with witches. Of course they did. XD
But the script made so many quick, delightful little moves (Sam flubbing their pseudonyms; the retarded appearance of "1520" after "Florence, Italy"; Dean's "I'm sure it's a different question"--which idk, I just loved because it acknowledged internally the rote speech patterns that accompany this kind of case, and the requirement of that).
And I adored the BM tag, as one does. I feel like the actual worth and craft of the conversations they tend to have during those scenes is somewhat variable, but this one really hustled, I feel like. Sam's dialogue had some real dimension to it, and I liked that there was a nod to the residual effects of Dean's ghost-strangulation. I thought the Dean confessional scene played well, too--and I don't think I'm typically one for these longer Dean expositions, because they make me feel naked by proxy and I just want to call all those words back into him, haha. But that scene really worked for me. <3
But mostly, keeping in mind that all I've seen of Rowena is 10x07, 10x17, and 10x16, so this could all be very wrong... some thoughts cast towards her corner: When she's thrown out of Hell and walks into the streets alone at the end of 10x17 (after shedding what I believe were genuine tears, tbh), I thought, you poor girl, there's no room here for your brand of loneliness.
Inasmuch as family is one of SPN's guiding themes, the flipside then becomes loneliness. And if over the years we've found that family has many dimensions and plenty of interpretations and expectations that must be grappled with, loneliness is much the same.
Rowena's villain-relationship to the Winchesters doesn't stem from wanting to use or manipulate them (YED, the Apocalypse), or underestimating them (Leviathans), or being eschatologically at odds with them (Godstiel, Metatron)--and while she does see herself and Crowley as technically superior to them, that's not ultimately what this all seems to be about. Not really. (When she first encounters Sam and Dean in 10x06, she seems genuinely concerned about her escape prospects, after all.) I think mostly she's just jealous of them.
With the exception of humanish!8x23!Crowley (hey, maybe it's a familial trait), I think the last person who was jealous of these dudes was that guy who'd taken the coin out of that wishing well. XD
She's jealous of all the attention they get (though arguably most of that attention is, uh, not desirable), and with the wealth of networks that coalesce around them--they're Men of Letters, they're in with the King of Hell, they also consort with angels, I mean. Given 10x17, she might even know a little bit about the Mark of Cain, and hell, why not be jealous of that too. Not for its effects or powers but for its notoriety. She downplays it as "just a curse," but stories are written, legends are told, legacies are formed; and these are all things Rowena has forever, ever wanted.
I'm not saying that we should feel bad for Rowena, necessarily, or sympathize with her. Because I also think the point of her is to largely exclude that relationship to her/that humanization.
So the fourth wall probably won't be rallying behind her any time soon, but I think it's interesting to have a character who shuffles herself endlessly from one site of flawed companionship to the next--her tawdry suitors back in the day (which, let's remember, gave her the pregnancy that got her expelled from the coven), the coven, the prostitutes she half-befriends, Crowley, whomever comes next--victim to, as Olivette put it, the conspiracies of her own mind, especially when contrasted against Sam and Dean, who do exceptionally little shuffling of companionship.
This isn't to say that Sam and Dean are the positive, feel-good example to Rowena's relational itinerancy, of course. I mean, their family's been generationally marked by weird insularity, and it's not like morbid codependence isn't a thing. S10 and previous seasons don't pretend interpersonal perfection by any stretch. Because family and loneliness, even as we describe them as flipsides of one another, aren't mutually exclusive. You can absolutely be lonely within your family, and you can feel alone even if that family explicitly announces its commitment to you/your well-being.
I don't think we can--or should--attempt to draw explicit parallels between these ideas and 10x16's MotW, but I think all of this, from both SamnDean's and Rowena's ends, play well in conversation with Sister Mathias and her Florentine ghost. I really liked that her relationship to Isabella, and the existence of ghosts, period, was such an explicitly private thing to her. So often, the mutual acknowledgement of the existence of ghosts serves as a relational anchoring point (okay, cool, we've all admitted we believe, let's salt and burn this thing, etc.) but for her, her ghosts are both a familiar presence and a deeply private experience. And someone else's expression of belief (or disbelief) has no bearing on her own relationship with them. That is, her faith and her way of being in the world were wholly independent from what she perceived the FBI to believe or not. Which we can then put against Isabella, who severed a finger in pursuit of a shared experience she was not destined to have.
It's a relational dysmorphia (tied up in self-harm) that's served as SPN's undercurrent since time immemorial, and which applies to Rowena as well. I mean, she carves herself up pretty good in 10x17. But more than that, she doesn't seem to understand the shape of the Winchesters' narrative or their world, or really her own. And so, as I said before, there's no room for her kind of loneliness. Even in the Winchesters' world, which has as many kinds of loneliness on tap as one universe (or four) could ever need.
As Sister Mathias and Isabella say:
MATHIAS: Loneliness is--
ISABELLA: Yes, it is.