This was always going to be a painful episode, and boy, it was a multi-hankey tear-jerker from start to finish. We’ve come to expect this out of Supernatural, but the stakes that were raised here have little equal in the show’s near 300 episode run. Let’s dive right in to Meredith Glynn’s gut wrenching brilliant episode.

Turn back now if you don’t want spoilers.

Our episode starts in Jack’s bedroom, with all three fathers watching over him as he rather cheerfully gasps his last breaths. Jack is at peace with his fate, and original recipe Team Free Will is anything but. Sam is melancholy and not leaving Jack’s side. Castiel is stoic, with a quiet fury as he stands beside a photo of Jack’s mother, Kelly. And Dean is just damned pissed off. He storms out of the room, and we’re right there with him – he has seen his share of death (we’ve watched it too), but something about Jack’s demise doesn’t seem right. It’s too soon. Castiel reminds him to stow his crap, and what Jack really needs is to be surrounded by the people that care about him most.

Jack asks Sam what happens next, after he passes. “I don’t know,” Sam admits and Jack smiles. “Then it’s going to be an adventure.” (Great nod to Peter Pan!) By the time Dean and Cas rejoin them, Jack’s gone. Cue the fandom tears.

We watch Team Free Will 1.0 try to decide what to do next. Of course they’re going to have a hunter’s funeral. But before they can make any decisions, Sam takes off. In the meantime, Dean, in a questionable move, calls Mary and leaves the news on her voicemail. (I cringed – poor Mary.) Dean and Cas go after Sam (in an interesting twist, Cas was driving Dean, and Dean wasn’t angry that Sam took the Impala), and when they find him, Sam is sitting beside Baby in defeat. Dean assumes he tried to “make a deal,” but Sam had just taken off to build a pyre. In the process, he actually breaks the ax he was using. They all feel like they failed Jack, despite how hard they tried to keep him alive. In the end, they decide to say goodbye tomorrow; “Tonight,” as Dean puts it, “we get loaded.”

In a sequence that will likely go down in Supernatural fandom history as one of the best, we see Team Free Will sitting in the kitchen, drinking, talking, laughing, and reminiscing about the son they lost. The music set to the scene is “Please Call Home“ by the Allman Brothers Band. Greg Allman wrote it in 1970, and in 1971 his brother Duane died in a motorcycle accident. The song has a melancholy tone, but it’s amazing to watch Sam, Dean, and Cas really enjoy each other’s company (along with several bottles of whiskey, and a couple of nougat candy bars). “Here’s to you Jack,” a very drunk Dean says, “wherever you are.”

We find our Nougat Son in Heaven with Sam, Dean, and Cas. His version of Heaven is burgers and a hunt, and if we weren’t crying before, we are now. Heaven short circuits, and Jack leaves his Heaven to investigate. Upon entering the brightly lit hallways, he is met with some sort of angry black goo that starts to chase him.

To no one’s surprise, Dean has one hell of a hangover the next morning, waking up face down on the kitchen table to the sounds of voices in the other room. When he stumbles in, he is face to face with an old friend – Lily Sunder. We met the angel killer last season, and the loss of her vengeance streak isn’t the only thing that’s changed – she’s aged quite a bit as well. She can’t read the angel tablets as they’d asked her to, but she does offer to resurrect and cure Jack using her magic. It would require Castiel to find Jack in Heaven and to put his soul back into his body long enough for the magic to work. The cost? Just a tiny bit of Jack’s soul will be needed to sustain his body. This doesn’t sit well with anyone, especially Dean, but it’s looking like their only option.

But Lily isn’t going to do this just out of the kindness of her heart. Turns out, she’d expected to die when she’d killed her last angel, but there’s a sliver of her soul left. What was once a guarantee of an eternity in Hell has now become a tiny possibility that she could be with her daughter again in Heaven. In order to ensure which direction she is going when she dies, they agree to summon Anubis, guardian of the dead (and also, Heaven’s temp when God took a vacation). Sam and Dean are still conflicted about it, but Castiel interrupts them with news from Heaven – apparently all of the gates are open and there’s a distress signal being sent out. He has no idea what he’s about to walk into.

In Heaven, Jack has found his way to his mother. It’s time to cry again, because we watch Jack and his mom meet for real for the first time. I absolutely love Courtney Ford as Kelly – the emotions she depicts from the joy of seeing her son, to absolute devastation that his appearance means he is dead were gut wrenching to watch.

Castiel arrives in Heaven to two dead angels… or so it seems, as Dumah wakes with a gasp. The black goo had gotten to her, and Castiel takes her with him to find Jack. They check his Heaven, and while they don’t find him there, they do run into Naomi. She informs Cas that Heaven is under attack, and that the black goo is actually “The Shadow” or what we’ve known as “The Empty”, the entity that rules over the void where angels go when they die. The Empty wants one thing – Jack. Castiel won’t let him get taken, of course, but Naomi reminds him – there are 46 billion human souls in Heaven that will be lost if it falls. What is the cost of one nephilim life compared to that?

“But our Nougat Son!” The fandom cries to deaf ears.

Sam and Dean successfully summon Anubis, who shows up looking like Heaven’s accountant. Lily asks the question she’s quite literally dying to know. Her hand over an abacus reveals that there’s more black than white on her record, which means she is damned. Sam and Dean threaten him to change it, but the truth is he is not the one who decides. It’s all of us, the individual moments of our lives, that adjust the scales until the moment that we die. Sam scrapes the sigil and releases the God, realizing that their own place in Heaven is not worth the risk.

Lily is ready to be gone but Sam and Dean stop her. I love them here, because while they’re a tough and threatening duo, they use emotion to appeal to her sense of reason and humanity. After all, she’s very aware of what it’s like to lose a child – something that they’re experiencing right now.

Cas finds Jack and Kelly, and we’re crying again, because it’s too beautiful to watch this small family reunion. Jack gets the full explanation of what’s going on and how he can be saved – but they’re quickly interrupted by Dumah. Only, it’s not really her – it is the Empty possessing her. I have to say that Erica Cerra’s depiction of the Empty is the best yet – creepy and frantic. She absolutely nails the cosmic entity’s sense of self-importance and gravitas.

Like a true Winchester, Castiel sacrifices himself to it – after all, he says, he is what the Empty actually wants. Upon consideration, the Empty agrees, but with one caveat: Castiel will not be taken now. The Empty wants to watch him suffer. So it will wait until Castiel is at his most happy, most content – and then rip him away to nothingness.

There’s a lot to unpack here about how the character of the Empty is an excellent allegory for depression – waiting in the shadows, until you almost forget it’s there, and then suddenly it rips you from your happiness and back into darkness. It’s quite literal here as well for the character of Castiel, who has always struggled with his own importance and place with the Winchesters and in this world. He seems to have found his stride in being Jack’s father (as Sam and Dean have as well), and we’ve watched Castiel smile and laugh more in the last season or two than we have in all other seasons combined. Part of that has been because he has allowed himself to be happy and experience joy in the people he loves.

The brilliance of Meredith’s writing here is that now she has taken a beloved character and made him into someone we actively do not want to be happy. I’m both incredibly angry and incredibly impressed. This also has a vague Buffy feel to it, for those of us who watched Angel turn to Angelus as his one moment of true happiness was achieved. We hope Team Free Will won’t suffer a similar fate.

Dean and Sam have Jack ready, and they pray to Castiel to send his soul back. Jack’s conflicted and angry because of Castiel’s decision, but Cas reminds him that he did it because he loves him, and that Sam and Dean love him too. And then we’re all crying again. In a melancholy moment, Castiel asks Jack to not mention the deal to Sam and Dean because “they’ll worry,” and Jack agrees. He says a tearful goodbye to Kelly, and with a minor face squishing, Castiel sends Jack back into his body.

He wakes with a gasp to Sam and Dean, who quickly hand him a spell to recite. Something works, his eyes glow and Dean asks him how he feels. “Good,” Jack says with a smile, and Dean goes in for the hug. They turn to thank Lily, but she’s gone, having died in the process of helping Jack.

Lily is now with Anubis, who asks her to try her hand at the abacus again. This time, it comes out more white than black. Evidently, her last act of heroism was enough to tip the scales. “Say hello to your daughter for me,” Anubis says, bidding her goodbye.

Outside of Kelly’s Heaven, Castiel runs into Naomi. She is not there to fight but to thank him for saving Heaven. As a reward, she offers to give him Michael’s location. We don’t get to know it, though, as the scene cuts away to Team Free Will 2.0 sitting at the dinner table. And now they’ve got a tentative plan at least – with Michael’s current location, and the knowledge that the spear can hurt him, they’ve got a direction. And as long as they have that, and all members alive and in relatively good health, they can take on the world.

Next week is the mid season finale, and it looks like we’re getting a Christmas episode that is sure to bring the pain. What was your favorite moment from this episode? Let us know in the comments below!