A year ago today on the fateful night of November 5, 2020, television history was made on Supernatural when the angel Castiel confessed his love for the one and only Dean Winchester. A long-time staple of the show, Cas had been with the brothers Winchester through good times and bad times, ups and downs, and to Hell and back (literally) ever since his character’s introduction in the show’s season 4 premiere, changing the trajectory of Supernatural forever.
Showcased on-screen for over 11 years, Castiel and Dean had a “profound bond” that was hard to ignore, becoming one of the show’s most quintessential examples of found family — one of Supernatural‘s most pervasive themes. With this bond undeniably cemented into the very foundation of the show, many fans speculated that there may have been even more emotion behind the angel and hunter’s relationship, showcased by Cas’ now-infamous reveal in “Despair.” In honor of the one-year anniversary of Castiel’s confession, we’re showcasing some of the best moments Cas and Dean have shared over the years.
“Lazarus Rising” brought us a pivotal moment when everything changed for Supernatural and effectively breathed new life into the show. With the introduction of Castiel and the angels, the show took on a new trajectory that shaped the rest of the series and the lives of Sam and Dean Winchester. So we must begin with the very first moment Castiel arrives on our screen by blowing apart a barn, shattering lights, and landing himself both a shotgun blast to the chest and a stab wound in a matter of seconds. A lovely way to be greeted. Our early iteration of Cas was a fierce warrior who was heaven-bent on saving Dean Winchester, whether Dean wanted that or not. It was Cas who forced Dean to reflect on his own self-worth and ultimately helped him grow as a character. In looking back on the series as a whole, the beginning of Destiel is certainly a bright spot!
The Purgatory Arc
The first Purgatory arc comprises some of the most beloved (and heartbreaking) moments for fans of Destiel. Taking place over the first few episodes of season 8, Dean is dealing with a lot of guilt (what else is new?) after Castiel is left behind in Purgatory. We get flashbacks to their time in Purgatory together, with Castiel pulling away from Dean so the Leviathan can’t hurt him as Dean tries to find Castiel, wanting to make sure they both make it out alive. We find out that Dean prayed to Castiel each night to find him — and that Castiel heard those prayers and had to ignore them to keep Dean safe.
In an even more devastating twist revealed in “A Little Slice of Kevin,” Dean’s memory of losing Castiel turns out to have been wrong. Beating himself up about “failing” Castiel when Castiel mysteriously returns (again, par for the course for Dean), Castiel realizes that Dean is deliberately misremembering the day Castiel was left behind and decides to show him what really happened. Dean believes he failed to save Castiel, while in truth, Castiel pushed Dean away to atone for his season 7 actions, thinking he deserved to stay in Purgatory. It’s another fundamental misunderstanding for the pair that says a lot about their individual characters, but the overall arc shows just how much they care for each other.
Season 15 brought us one of the best speeches from Dean Winchester of the series in episode 9, “The Trap.” Dean and Cas have once again been separated in Purgatory, and Dean is faced with the real possibility of losing Cas (again) forever. In a heartbreaking and tender prayer to Cas, Dean apologizes for letting him leave the bunker. He apologizes for his anger, for his frustration, for everything he’s done to Cas and makes it clear Cas is more important to him than any of it.
“I don’t know why I get so angry. I just know that it’s just always been there, and when things go bad it comes out. I can’t stop it no matter how bad I want to. I forgive you, of course I forgive you. I’m sorry it took me til now to say it.”
This moment culminates in 15 years of character development for the often quick tempered Dean who is coming to terms with the fact that he hides his fear behind rage. Dean is more self-aware in this moment than is comfortable for most, and it’s why his prayer shines in the minds of Destiel fans. It’s the apology Cas needed from Dean, it’s delivered in a heartbreaking prayer at the proverbial final hour and was made all the more moving by the hug when Dean and Cas reunite. In Cas’ perfect understanding of Dean, he simply tells him he heard the prayer, and they need not say anymore. All is forgiven.
Some of the most powerful Destiel moments are the ones that occur while one of the characters isn’t even in the room. In “Nihilism,” Sam, Jack, and Castiel are desperate to get Dean back as his body is possessed by Michael and monsters make their way to the bunker. Michael cruelly twists the knife as Team Free Will 2.0 listens to Michael calmly discuss killing everyone they love (Jensen Ackles, once again knocking it out of the park). In a hair-raising scene, Michael wonders exactly why Castiel cares: “Tell me. Why do you love this world enough to risk your own life?”
Castiel listening to Michael mock his loyalty while wearing Dean’s face is sad enough, but when Castiel and Sam journey inside Dean’s head to kick Michael out, we also see Dean’s traumas playing on a loop. We also see his happy memories as Sam and Castiel find the fantasy Michael has hidden Dean in, and Castiel has to plead for Dean to wake up and remember what happened: “It’s just a dream, Dean. That’s all it is. Please, you have to — you have to try to remember, because the people in your life — in your real life, out there — we need you to come back.” It’s not the first time Dean or Castiel has begged for the other to wake up and come back to their real life, but it cuts deeper knowing that Castiel had to watch the man he loves disappear and be replaced by Michael.
Throughout the show, Dean and Cas managed to prove over and over again that the bond forged between them could transcend just about anything — Heaven, Hell, or anyone else that dare stand in their way be damned. This is just one of many of those moments that shows how deep their connection goes. In season 8, we find out that Cas had endured literal millennia of being controlled in some way or another by Naomi’s reconditioning, with Heaven constantly working to mold the angel into the perfect soldier again and again. And when the big halos in the sky come knocking at Castiel’s door this time in the quest for the angel tablet, they order him to do the unthinkable — kill Dean.
A heartbreaking scene ensues as Cas, under the seemingly inescapable influence of mind control, absolutely bashes an ever-loyal Dean, staunchly begging his best friend to come back to himself. Just when it seems too late, three desperately whispered words by the elder Winchester get through: “I need you.” This painstakingly vulnerable admission serves as the impetus for Cas to snap out of his stupor, tenderly healing Dean. Once again, the shakeable, but unbreakable bond between a mere man and his angel fundamentally change the course of the story, something that would continue to pervade storylines throughout the show’s run.
One of fans’ most beloved Dean and Cas moments by far, “Tombstone” has cemented itself into the minds of the fandom as one of the greatest Destiel moments of all time. The pure, unfettered joy that Dean exudes throughout this episode simply from playing cowboys with Cas back by his side is so telling to the effect the angel’s presence has on the hunter, especially when looking at his behavior not 24 hours prior.
Cas’ death at the hands of Lucifer was absolutely devastating for Dean. Often dubbed by fans as the “Widower Arc,” Dean spirals hard following the angel’s passing, becoming extremely depressed and reckless and putting himself in harm’s way without a care if he lives or dies. At one point, he even tells the newly minted Death, Billie, that he doesn’t care if she reaps him, as he’s tired of losing and failing so much. He looks like a man on whom the weight of the world has rested for too long. However, as soon as Cas is resurrected by Jack, Dean’s temperament changes drastically almost instantaneously, something that Sam mentions when he says it’s nice to see his big brother smile again.
“Well, I said I needed a big win. We got Cas back. That’s a pretty damn big win.”
“Tombstone” exemplifies some of the best (but rarely showcased) lighthearted aspects of Dean and Cas’ friendship. Dean’s contagious excitement and Cas’ begrudgingly fond agreement to strut the streets donned in Stetsons and their best southern affectations — and of course, the reveal of the movie nights that educated Cas on his ranger etiquette in the first place — are all small details that reveal the depths the pair go to in order to make each others’ days brighter. And what can we say? The duo looks good in their getup.
The introduction of the Mark of Cain in season 9’s “First Born” was a huge shake-up for the show, and it had lasting repercussions for Dean and Cas. The Mark enabled the Winchesters to be free of Abaddon, but at what cost? For much of seasons 9 and 10, it seemed like the answer might be Dean himself, a price that Castiel was simply not prepared to pay. His desperation to find a cure for Dean — despite his fading grace and heaven’s problems — further demonstrated the devotion interwoven into their relationship. He refused to give up on Dean, even when Dean was at his worst; even when Dean had given up on himself. Another thing that makes the Mark of Cain arc so painfully beautiful for Destiel fans is the deliberate parallel drawn between Cain, Abel, and Colette in the past and Dean, Sam, and Cas in the present. Even under the influence of the oldest curse in existence, Dean and Castiel’s profound bond shines through. Again and again, we’re shown that Dean and Castiel’s bond is different. Dean even reneges on his deal with Crowley and gives the First Blade to Cas during “The Executioner’s Song,” entrusting him with the only thing that can kill a Knight of Hell.
Cain himself brings Dean’s relationship with Cas to the forefront when he says, “First … first, you’d kill Crowley. There’d be some strange, mixed feelings on that one, but you’d have your reason. You’d get it done, no remorse. And then you’d kill the angel, Castiel. Now, that one … that I suspect would hurt something awful.” The idea that the curse might cause Dean to harm those he loves is chilling enough, but it’s even more heart-wrenching to see it play out on screen. By season 10 episode 22, “The Prisoner,” Dean is fighting a losing battle against his bloodlust. Savagely beating his angel and threatening to kill Sam and him both if he sees them again, Dean is a hair’s breadth away from the killer Cain said he would be. As he watches the corrupting influence of the Mark further consume the man he loves, Castiel’s impassioned plea is filled with more emotion than we’d once have believed the stoic, season 4 solider capable of:
“Maybe you could fight the Mark for years. Maybe centuries, like Cain did. But you cannot fight it forever. And when you finally turn, and you will turn … Sam, and everyone you know, everyone you love … they could be long dead. Everyone except me. I’m the one who will have to watch you murder the world. So if there’s even a small chance that we can save you, I won’t let you walk out of this room.”
But, even then, with the curse of the Mark of Cain burning not just into his skin but into his very soul, Dean cannot bring himself to kill Castiel. Instead, with blood on his hands and a weapon mere inches from victory, Dean abandons the blade, turns, and leaves.
While there were plenty of intriguing Supernatural plotlines over the years that left audiences wanting more, one of the biggest teases was the single-episode glimpse into the Croatoan zombie apocalypse in season 5’s “The End.” Dean finds himself tossed into a grim, dangerous alternate universe in the future, courtesy of Zachariah. When he comes across Camp Chitaqua, which is led by his cold, hardened future self, he finds a version of Castiel that’s very different from the one he left behind (“I’ll just wait here then”).
Dean may have only stepped five years into the future, but those years have done a number on his friend, who he’s shocked to learn is no longer an angel. At this point in the series, the Dean-shaped chips in Castiel’s angelic armor had begun to show periodically, but he was still very much an awkwardly stoic angel of the Lord. Endverse!Cas, on the other hand, is carefree, open, loose, and an entirely eye-opening experience for Dean.
Beyond the fact that Endverse!Cas and 2009 Dean’s interactions are just wholly enjoyable (and we deserved much more of them — “I like past you”), the entirety of this episode is so important for these two because it’s one of the first times that Dean realizes that Cas isn’t invincible. In a short amount of time, he’s grown very used to depending on Cas’ angelic powers — hence why he sought him out at the camp and asked him to strap on his wings and take him back to the past (although 2009 Cas did end up saving him from Zachariah after all, because of course he did). But this Cas is “powerless, hapless, and hopeless,” which further fuels Dean’s fury when he realizes that Endverse!Dean intends to lie and use him as a decoy. It’s also worth noting that when Dean inquires about Cas’ whereabouts, Chuck comments, “I don’t think Cas is going anywhere,” a layered sentiment that would ring true throughout the series as a whole.
Can an angel feel? The question hovered in the background of Supernatural — both in canon and in fanon spaces — for years. Castiel was always a little different, sure; he had a crack in his chassis, after all. He learned about humanity, about family, about love. But what kind of love? It’s interesting that the show chose the episode right before “Despair” — episode 17, ” Unity” — to show, unequivocally, the answer to that question in the form of Adam and Serafina, the first man and his angel girlfriend of 300,000 years. Then, in “Despair,” Castiel got to say his piece.
And as much as Castiel deserved to finally say it, Dean deserved to finally hear 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 see 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.”
Bobo Berens wrote Castiel’s confession speech to be an endorsement of fans’ reading of the character as queer, canonically confirming him as somewhere on the LGBTQIA+ spectrum. But he also used it to skillfully cut right to the core of Dean and his character development over the entire past decade and a half. Castiel sees Dean. He always has. Dean’s angel was never pulled in by his performance, he was pulled in by all that Dean is and always has been. Dean has always struggled with seeing his own worth. (Did anyone out there manage to watch this scene and hear “daddy’s blunt instrument” without flinching?) He learned to weigh himself by what he could provide for others, and in this scene, Castiel gifts him with something instead: love. And he doesn’t even ask for anything in return; Castiel’s happiness “is in just being.”
“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.”
The depth of emotion both actors put into this scene is astounding. It is the ultimate Destiel moment, not just because of Castiel’s raw, honest confession, but because of Dean’s clear terror and sorrow — not as he realizes what Castiel is saying, but as he realizes what it means, what is about to happen. Dean’s grief begins before Castiel has even gone, all over his face while Death is still beating down the door and in every shaking breath as the Empty arrives, and his angel is taken away one last time.
Dean and Castiel’s relationship was characterized by two things from the very beginning: devotion and sacrifice. No matter what mistakes they made or how angry they got, they always came back to each other in the end, and they put each other first far more than they should; ahead of themselves, ahead of others, ahead of the whole world on more than one occasion. It’s only fitting that their final on-screen scene together was steeped in the same devotion and sacrifice they’d been practicing for over a decade.
Castiel’s love isn’t an obligation. They aren’t related; he isn’t Sam, or John, or Mary, they may be family, but they aren’t the kind that came premade. Castiel’s love for Dean was born without expectation, and it exists simply because of who Dean has shown himself to be, even when Castiel has often seen the worst Dean has to offer. Doesn’t everyone who is any way romantically inclined want that? No matter what expressing love means to someone personally, the idea that there might be someone willing to care for even the parts of us we don’t think deserve it … that turns “Despair” into hope for a lot of people.
No matter what did or didn’t happen after Castiel’s confession in “Despair” and for the remaining 2 episodes of the season, this — this heartbreakingly beautiful Destiel moment — deserves to be cherished and lauded for everything it represented and confirmed.
Castiel learned love through Dean; he learned love by loving. He may be an angel, but there is no experience more human than that.
“The Things We Left Behind”: Dean doesn’t think he’s a role model. Castiel disagrees.
“The Future”: The mixtape. Need we say more?
“Good God, Y’all”: Castiel rebelled for Dean, is a thank you too much to ask for?
“Stairway To Heaven”: Castiel is in love … with humanity. “Humanity.”
“Survival of the Fittest”: Meg claims Castiel was Dean’s boyfriend first.
“Destiny’s Child”: Dean has some theories about the Occultum. Castiel wonders if this is Hell.
“Yada Yada Yada”: Balthazar does not want to be mistaken for the angel “in the dirty trench coat” who’s in love with Dean.
“Hello, Cruel World”: Dean hangs on to Castiel’s trench coat. You know, in case he comes back and needs it.
“The Third Man”: Sorry Sam, Castiel just has a more profound bond with Dean. To be fair, he wasn’t going to mention it.
“Fan Fiction”: Dean getting flustered at Sam guessing his and Cas’ ship name … not to mention the real-life couple dressed as the hunter and his favorite heavenly being.
“Lily Sunder Has Some Regrets”: Just … the whole thing.
There are countless other moments between these two characters that we could list if we had the time or space. What favorite Destiel moments did we miss? Let us know in the comments!