Revisiting the lyrics to "Watching Over Me" in the context of what Jensen has said before and most recently, about Dean's thought process in the aftermath of Cas's declaration, as he sat sobbing on the dungeon floor in the hours that followed.
We know Jensen has Thoughts about what Dean was going through in that scene. He’s said that in the aftermath is when Dean really processed and Understood Cas’s words. Dean was too overwhelmed by everything happening in the moment, but it’s after that everything sinks in. And it’s also in this “after” that Dean mourns and regrets never saying anything back, and that Jensen thought as Dean while filming, “I should’ve said I love you and hugged him.”
So with that context, I’m revisiting the lyrics of "Watching Over Me":
Lay it on
Now that I can see
Couldn't barely talk
Without the will to breathe
Didn't hear the strength within your words
And what they mean
You were watchin' over me
This first stanza details exactly what Jensen has spoken about before, Dean left in the aftermath. Dean now looking back, “now that [he] can see” what Cas’s words meant, “the strength within” them. And at the time, in the moment of Cas’s declaration, Dean was overwhelmed, couldn’t talk, couldn’t breathe. He didn’t hear what it really meant in the moment, but now on the dungeon floor it’s all hitting him.
You can hear the call
When trouble's on the way
Who said the beast was gone?
He was only just away
Tryin' to find the peace and always knowin'
I was never really free
You were watchin' over me
In the second stanza, I interpret this as sort of jumping into the future, into 15x19 and 15x20 (from a Chuck Won angle, they were never really free), but also touching on the pervading theme throughout season 15, about realizing they were never truly free. The beast is Chuck. At the start of s15 they believe Chuck has “gone” and abandoned them but he wasn’t truly gone, “only just away.” Dean especially spends much of the season really struggling with the knowledge that they were just pawns in Chuck’s game.
Cas also was always the wrench in Chuck’s stories, always disrupting the narrative. If we continue to presume the “you’s” in the song are Cas then “You can hear the call / When trouble’s on the way” could mean that Cas was more in-tune with celestial things, knowing when trouble was on the way, or just always willing to step up to the plate when trouble came knocking. I think, with the refrain of “You were watchin’ over me” it’s clear that Dean sees Cas as someone who was always looking out for him, and that he now understands Cas wasn't simply "watching over him" as an angel, but because he cares deeply for Dean. (Even when Cas wasn’t physically there to “watch over him” Cas was often doing things with this intent—whether his plans panned out or not, I think Dean sees and acknowledges the intent behind a lot of Cas’s actions as being protective in nature).
With the will to look away
When I was fallin' down
Crawlin' in the dirt?
I can see these lines as being about the moment when Cas pushes Dean aside for the Empty to take him. Cas has always been “watchin’ over” Dean but in that moment he had “the will to look away” as he smiles and saves Dean one last time. And Dean may not literally have been “crawlin’ in the dirt” but metaphorically he feels like this, as he tries to get his bearings after “fallin’ down”, trying to get back up but paralyzed to do so. Internally he’s grappling, crawling through the dirt of this awful moment.
Is it fair enough to say
That I needed you through the crazy pain
Of livin' here with all this hurt and what I feel?
Dean, broken and defeated in his grief, bargaining, praying, thinking: how can I go on without you, Cas? How can he go on “livin’ here with all this hurt” and what [he] feels !!!! WHAT HE [DEAN] FEELS!!! What does he feel? Going back up to that first stanza, and how Dean couldn’t speak, couldn’t breathe. Thinking back to what Jensen has said, about him thinking as Dean in that moment, “I should’ve said I love you and hugged him.” And here Dean is wondering, “how the hell am I supposed to live like this? What am I supposed to do with all this “crazy pain” and all these words left unsaid and what I feel."
Another angle of interpretation is also, “I needed you here to get through all of this, to get through living in this world we live in” looping back to the stuff about Chuck and Free Will. He needed Cas with him, by his side, as his best friend, partner, everything, to get through the horrors of living the lives they live. And now Cas is gone, and how can he go on?
All I touch and how I steal?
This line is interesting to me. It feels like self-blame. Guilt. Echoing the sentiment of “the very touch of you corrupts.” In conjunction with the next two lines, Dean’s feeling regret. He let it all “slip away.” But also this line is in the same stanza with the previous lines. And reading it all together there’s this feeling of “I needed you. I needed you here in my life through all the horrible pain, through everything we’ve been through together, I’ve always needed you, even when I’ve been at my worst, even when I ruin the things I touch. I’ve always needed you here by my side through it all."
The fantasy was far too real
Oh, I let it slip away
This could mean so many things depending on your reading of Dean and his feelings for Cas. I don’t know if this is what Jensen was thinking when he wrote these lyrics, but my personal interpretation of these lines are, well Dean had this fantasy in his mind, of them winning, of them getting out. Of one day being able to declare his own feelings for Cas (the Trap “there's something I need to say—”). But in the end he never got to speak his feelings. Everything slipped away from him so fast. All his hopes and dreams, gone. Also, if you take into consideration the idea that Dean was pining after Cas but never thought Cas would or could feel the same way because of various reasons, this line could also be Dean mourning that when it finally happened and his fantasy (hearing Cas say i love you romantically) came true he didn't even realize that's what Cas meant! He let the moment slip away! His big moment! He didn't even get to say "I love you" back. His deepest fantasy finally made real and then he let it all slip away.
Another more general interpretation is just this sense of regret, of letting Cas go, of not being able to do anything in that moment to stop him from leaving, feeling helpless and hopeless and blaming himself.
Didn't hear the strength within your words
And what they mean
You were watchin' over me
And again, the refrain. In the moment of Cas's declaration he didn’t hear what Cas’s words really meant. Now, he’s processed them and understands the fullness of Cas’s love, that it was romantic, that Cas was always watching over him, protecting him, saving him.