It's a funny thing, all of them gathered together, working on a 'hunt'. This is Heaven, and they're all choosing to be here, the family business really is an essential part of what makes them who they are.

Sam told Jess everything, she took it all in stride, and he still stands by his initial assessment, Jess is way out of his brother's league. Still, seeing them happy together might be the best thing that's ever happened to Dean. And Jess is smart, so she takes to hunting like a duck to water, and a little bit of him wonders what Sam's life might have been if he'd just told her the truth from the start. Could the three of them have hunted together all those years?

"So," Jess says and they let her try, because there's no rush, and because it might be good to get a fresh perspective. "If the Empty is the only one who can release people, you'll need to make a deal for them."

All four Winchesters wince because that's something that has never ended well for their family. He can't say Jess is wrong though either.

"The only thing I know the Empty ever wanted was quiet," he says. "So what? We bust in there, go all Animal House, and say we'll quit it when it hands Benny and Crowley over?"

"That sounds dangerous, Dean," his mom warns. He knows what she means, poking the bear is risky, but his reply is out his mouth before he knows it.

"Benny's worth it."

And then suddenly every pair of eyes in the room are on him, filled with various degrees of shock and fondness. What? Isn't he allowed to be in love too?

It's his dad who breaks the silence.

"Well I for one can't wait to meet him."

His dad always had a way of saying the right thing at the right time to get everyone to fall into line, and they get back to work, his mom giving him an extra smile as they do.

"The biggest problem," Sam points out, "is figuring out how we contact the Empty. We used Billie before but we can't do that now. How did Cass do it, Dean?"

He's never actually told anyone this whole story before, mostly because it felt unfair to Cass, to share his biggest secret without asking. He thinks about telling it now, but then he decides maybe he should just pray and let Cass speak for himself. That feels cruel though, to ask for Cass's help so he can find a happy ending with someone who isn't him.

"Can't we just call Jack?" he suggests. "Has anyone seen him up here?"

It turns out no one has. His mom and dad and Bobby all saw Cass a while ago, but apparently Jack's been true to his word about a more hands-off approach. And he certainly doesn't sit on a throne all day expecting to be worshipped like that douchebag Chuck was known to do.

"Dean?" Sam says again. "What did Cass do?"

He can't lie so he spills.

"He made a deal to save Jack, and the price came due."

"What price?" Sam pushes. "It might give us a clue about what we could offer."

"A life for a life. When Cass experienced a moment of true happiness, the Empty would take him. It was meant to come at a random time I think, to pluck him away when it would be as cruel as possible, but Cass forced it. He made his own happiness and then it came for him."

"What did he do?" his mom gently prompts, not because it's vital information, but because she can see that he's struggling, and because after him and Sam, she probably knew Cass best.

He looks at her when he says it, because it's hard to say and she's his mom.

"He told me he loved me. Finally admitting his feelings is what did it."

There's silence again, and he knows how it makes him look, chasing Benny when Cass, who was there all those years, wants him, but that's the thing about being in love, you don't choose it.

It's Bobby who rescues him this time.

"Okay, so that way in isn't an option. Maybe Dean's right, maybe we do need Jack."

"I don't know," his dad says. "As much as I love you Dean, and son I honestly couldn't be prouder, we have to stop and ask ourselves if there are gonna be repercussions here. You boys fought your whole lives to achieve this status quo, Heaven is a better place for billions of souls because of you both, so we have to be careful we don't tip the scales the wrong way."

He doesn't know what to say, because his dad might be right, but it also goes against everything in him not to fight for what he wants. Usually that desire was to save the world, this time it's to be reunited with someone he loves. Can he simply let it go for the sake of everyone else? He's a Winchester, of course the answer is yes.

And then, he might not have to. Cass appears, it's the first time Dean's seen him since that day at the bunker, the day that Cass died, the day he confessed his feelings.

"Cass..."

"Hello Dean," the angel smiles. "Hello everyone."

They all return the greeting, some a little nervously, because Cass is different than the last time they saw him.

"You look..."

"Angelic?"

"Yeah..."

Cass is actually glowing, in fact he doesn't look corporeal at all. He's made of light, of grace, Dean realises. And he's beautiful in the way a sunset or a fresh wax job on the Impala is beautiful.

"I always wondered what you really looked like..."

"Does it make you uncomfortable? I can change."

"No. No, it's a good look. Very divine."

Cass smiles, glowing brighter.

"I heard your plans-"

"I'm sorry," he instantly apologises. Even though he's not in love with Cass, he still hates to think of him not getting what he wants.

"Dean, it's okay. Things have changed. Again. I'm fulfilled."

"I hope so, pal," he offers with utter sincerity, trying to touch Cass's shoulder but his hand slips right through. Cass gives him a little smile, and carries on.

"Now, as for this plan to bring a vampire and a demon back from the Empty, Jack won't get involved."

"It can't be done?" Bobby questions.

"No, it can," Cass clarifies. "It's just that you'll need to work it out for yourselves."

Dean fights an inner battle, trying to decide if he should ask for help, wondering if that's going too far, but in the end he has to know.

"Do you have a way in, Cass?"

"There are only two ways. Dead supernatural beings go there, or The Shadow summons you."

"So we need to get The Shadow's attention?"

"That's a dangerous thing to do. There's no guarantee it would let you go again. Besides, you have to be something divine, demonic or monstrous, for it to work."

What he's hearing is that it's impossible, but that's never stopped them before.

"There must be a way..." They've never not figured things out before.

"Dean, can we talk? Alone?"

"Yeah, sure," he agrees, following Cass outside because he can't refuse him after what happened.

"Cass, I-"

"Dean, really it's okay. I'd do this for you myself except I can't right now. Not without taking another vessel which I won't do."

"I get it, Cass. It's not up to you anyway."

"I think your best bet will be riding a demon in. I think Rowena could help you with that, so what you need to do is go to Hell."

"Hell? How?"

"Heaven and Hell are connected, there's a path, a stairway, but it's difficult to traverse. You have to be very strong and very focused to make it all the way."

"And if we don't make it?"

"You'll just get spit back out here. It's usually a path travelled in the other direction."

"You mean souls climbing out of Hell?"

He'd never thought about it like that, but being able to work for redemption makes sense.

"Exactly. One thing it will demand of you is complete honesty. So can I ask you Dean, was there ever a chance for us?"

Cass is aware now that gender wasn't the issue, so it's a fair question to ask.

"Maybe at the start there could have been, but you broke my trust, Cass. Big time. It was never the same for me after that."

Cass nods, glow dimming a little.

"That's what this Benny has that I don't?"

"He's never let me down, Cass. No one has ever loved me as much as he did."

"I know that's not true."

"Maybe, but no one has ever loved me as selflessly as he did."

Cass nods again, he can't deny that. There were times when Cass asked too much.

"Okay, Dean. You're ready. I'll show you the entrance to the stairway. But after that it's up to you."