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. Heโs said that in the aftermath is when Dean really processed and Understood Casโs words. Dean was too overwhelmed by everything happening in the moment, but itโs after that everything sinks in. And itโs also in this โafterโ that Dean mourns and regrets never saying anything back, and that Jensen thought as Dean while filming, โI shouldโve said I love you and hugged him.โย
So with that context, Iโm revisiting the lyrics of "Watching Over Me": ย
Lay it onย
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, โnow that [he] can seeโ what Casโs words meant, โthe strength withinโ them. And at the time, in the moment of Casโs declaration, Dean was overwhelmed, couldnโt talk, couldnโt breathe. He didnโt hear what it really meant in the moment, but now on the dungeon floor itโs 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 โgoneโ and abandoned them but he wasnโt truly gone, โonly just away.โ Dean especially spends much of the season really struggling with the knowledge that they were just pawns in Chuckโs game.
Cas also was always the wrench in Chuckโs stories, always disrupting the narrative. If we continue to presume the โyouโsโ in the song are Cas then โYou can hear the call / When troubleโs on the wayโ 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 โYou were watchinโ over meโ itโs 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 wasnโt physically there to โwatch over himโ Cas was often doing things with this intentโwhether his plans panned out or not, I think Dean sees and acknowledges the intent behind a lot of Casโs 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 โwatchinโ overโ Dean but in that moment he had โthe will to look awayโ as he smiles and saves Dean one last time. And Dean may not literally have been โcrawlinโ in the dirtโ but metaphorically he feels like this, as he tries to get his bearings after โfallinโ downโ, trying to get back up but paralyzed to do so. Internally heโs 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 โlivinโ here with all this hurtโ and what [he] feels !!!! WHAT HE [DEAN] FEELS!!! What does he feel? Going back up to that first stanza, and how Dean couldnโt speak, couldnโt breathe. Thinking back to what Jensen has said, about him thinking as Dean in that moment, โI shouldโve said I love you and hugged him.โ And here Dean is wondering, โhow the hell am I supposed to live like this? What am I supposed to do with all this โcrazy painโ and all these words left unsaid and what I feel."
Another angle of interpretation is also, โI needed you here to get through all of this, to get through living in this world we live inโ 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 โthe very touch of you corrupts.โ In conjunction with the next two lines, Deanโs feeling regret. He let it all โslip away.โ But also this line is in the same stanza with the previous lines. And reading it all together thereโs this feeling of โI needed you. I needed you here in my life through all the horrible pain, through everything weโve been through together, Iโve always needed you, even when Iโve been at my worst, even when I ruin the things I touch. Iโve 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 donโt 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 โthere's something I need to sayโโ). 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 didnโt hear what Casโs words really meant. Now, heโs processed them and understands the fullness of Casโs love, that it was romantic, that Cas was always watching over him, protecting him, saving him.