Supernatural was about two brothers who traveled around, hunting monsters, gods, and everything in between. In season five, the angel Castiel becomes a series regular, and Team Free Will is officially formed. Sam, Dean, and Castiel fight against fate to save billions of lives.
As Supernatural progressed, Castiel became family to Sam and Dean, but audiences couldn’t help but notice that Dean and Castiel had a special bond. Fans started interpreting the subtext between the two as romantic, and it became a very popular «ship» within the fandom. At a recent convention, «Destiel shippers» got a treat when Jensen Ackles confirmed that one of his band’s songs was partially inspired by the Dean and Castiel relationship.
Dean and Castiel Share a Profound Bond
Castiel first appeared on Supernatural in season four. He was the angel who gripped Dean tightly and raised him from perdition. From early on, Castiel seemed to have an interest in Dean and his humanity. The more time he spent with the eldest Winchester, the more he started to doubt his orders. By season five, Castiel was a renegade angel, working with the Winchesters to stop the impending apocalypse.
The bond between Dean and Castiel continued to evolve and deepen as they saved the world together. Some moments that highlight the deep bond they share include, after Castiel’s betrayal and apparent death in season seven, Dean is sent into a downward spiral, slowly losing faith in himself and everyone around him. When Castiel is back, despite his numerous infractions, Dean can’t help but forgive the wayward angel. In the finale of season eleven, Dean has a heart-to-heart with Cass, where he tells him, «You’re the best friend we’ve ever had. You’re our brother, Cass. I want you to know that.» After the world is saved, they all assume Dean is dead. Castiel is understandably delighted when he learns Dean is alive and immediately hugs him. During the mid-season, Castiel is sure he’s about to die and makes a «deathbed speech,» begging the Winchesters to save themselves.
«No, you listen to me. You– Look, thank you. Thank you. Knowing you, it… it’s been the best part of my life. And the things that… the things we’ve shared together, they have changed me. You’re my family. I love you. I love all of you. Just please… please, don’t make my last moments be spent watching you die. Just run. Save yourselves. And I will hold Ramiel off as long as I can.»
After Castiel dies in the season twelve finale, Dean is notably depressed. When Castiel returns from the Empty, Dean regains his childlike enthusiasm in the next episode, as the case takes them to an old western town. Sam observes how Dean is in a much better mood after getting Cass back. Following the events at the end of season 14, Dean is angry about Mary’s death at Jack’s hand and takes it out on Castiel. When the two go to purgatory and get separated, Dean prays to Castiel, apologizing for not stopping Castiel from leaving after their fight.
«Cass, I hope you can hear me… that wherever you are, it’s not too late. I should’ve stopped you. You’re my best friend, but I just let you go. ‘Cause it was easier than admitting I was wrong. I—Ohh. I don’t know why I get so angry. I just know—I know that it’s, it’s just always been there. And when things go bad, it just—it comes out. And I can’t, I can’t stop it. No matter how, how bad I want to, I just can’t stop it. And, and I—I forgive you. Of course, I forgive you. I’m sorry it took me so long. I’m sorry it took me till now to say it. Cas, I’m, I’m so sorry. Man, I hope you can hear me. I hope you can hear me.»
In one of the final episodes of the series, Castiel uses his final moments to confess his love for Dean and save him from Billie. Knowing the Empty was the only thing that could stop her, Castiel realizes his moment of true happiness when he speaks his truth in an emotional speech to Dean, ending with «I love you.»
«I always wondered, ever since I took that burden, that curse, I wondered what it could be? What my true happiness could even look like. I never found an answer because the one thing I want… It’s something I know I can’t have. But I think I know… I think I know now. Happiness isn’t in the having, it’s in just being. It’s in just saying it.
I know. I know how you see yourself, Dean. You see yourself the same way our enemies see you. You’re destructive, and you’re angry, and you’re broken. You’re «daddy’s blunt instrument.» And you think that hate and anger, that’s… That’s what drives you, that’s who you are. It’s not. And everyone who knows you sees it. Everything you have ever done, the good and the bad, you have done for love. You raised your little brother for love. You fought for this whole world for love. That is who you are. You’re the most caring man on Earth. You are the most selfless, loving human being I will ever know.
You know, ever since we met, ever since I pulled you out of Hell… Knowing you has changed me. Because you cared, I cared. I cared about you. I cared about Sam, I cared about Jack… I cared about the whole world because of you. You changed me, Dean… I love you.»
Jensen Ackles was asked about what Dean’s response might have been during one of the Supernatural The Road So Far Conventions, which was in Oklahoma City this past weekend. When answering the fan question, Ackles revealed that he had an answer when they were filming the next scene and used it to inform his performance.
«…I had an answer for that in the next setup—camera setup—after Castiel was taken, and Dean’s on the floor and puts his—I put my head in my hands. At that moment, I did that not because I just lost, well because I lost Cass, but also because I didn’t say anything, I didn’t give him anything. And what I had in my head was I should have said, ‘I love you, too,’ and hugged him. And I know that some, y’know, people out there that might try to sexualize that in a way, and it doesn’t have to be that… what was in front of me was a family member and someone that was a brother in arms, and someone that Dean truly loved, much like Sam. And so losing—I mean, essentially, he lost his brother in that moment. And that’s how I think—that’s how I played it from Dean’s perspective.»
Jensen Ackles Confirms "Watchin' Over Me" Is About Dean and Castiel
In 2021, Jensen Ackles’ band, Radio Company, released a track titled «Watching Over Me.» Supernatural fans were quick to theorize that the song was about Dean and Castiel. At a convention a few months ago, Misha Collins said that the song was, in fact, about the angel and
his favorite Winchester, but fans still wanted to hear from one of the songwriters himself.
Last weekend at the Purgatory 9 convention, Jensen Ackles was asked by a fan if «Watching Over Me» was inspired by the relationship between Dean and Castiel. Ackles warned the crowd not to get too excited and said that Radio Company’s songs aren’t literal, and that «they are analogies.» Ackles elaborated, saying, «There’s a way to kind of read two meanings into them.» The actor went on to confirm that Castiel was part of his inspiration when writing the song. «Yes, ‘Watching Over Me’ was definitely—not all of it, but there were many lyrics in there that were inspired by that story,» Ackles said.
The title of the song directly echoes a line that Castiel had in Season 8. When Sam, Dean, and Castiel run out of leads for the night, Dean calls it, saying he needs to get his four hours of sleep. Castiel responds, saying, «I’ll watch over you.» Other, more subtle lines of the song that could be about the angel are, «You can hear the call when trouble’s on the way.» The lyrics could refer to Dean’s prayers to Castiel. Another couplet that listeners can’t help but think of Castiel when hearing is, «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?» Considering how much Dean needed Castiel and how defeated and downcast he was when Cass died, it could definitely be about the angel.